“Would It Be Cheating if I Taught My Sugar Daddy Tennis?”


I’m in a relationship with a guy I truly adore and love and eventually plan to marry. However, he doesn’t spoil me the way I like and doesn’t really offer me any financial help even though I desperately need it right now. I just moved and I am helping my mom start her business and at the same time trying to take care of my pregnant little sister.

In the midst of all this change I met a guy who is about 13 years older than I am. He’s married and I guess you can say he’s looking for a little excitement. We don’t have a physical relationship, but he likes spending time with me and likes to give me money and gifts. And he really helped me out when I was going through a rough time. We are friends and, instead of sleeping with him, I try to offer him advice about his family life and working things out with his wife. I don’t find him attractive and he’s definitely not someone I would ever go for, but I stay because of the money. It’s reeeeaaallllyyy easy money. And in some sense I feel good about helping him.

So here’s my current situation: I ended the “sugar daddy” relationship because he crossed the line and sent me flowers at work while my boyfriend was there. I was really relieved to get out of our arrangement because I felt horrible about lying to my boyfriend even if I didn’t have a romantic or physical type of relationship with that guy. But we have thought of a brilliant arrangement, though, that makes me feel a little easier about spending time with him and making some serious money again. I could teach him tennis lessons. That way he can pay me without it looking strange and he can still spend time with me without my boyfriend getting alarmed.

So what do you think? I know I am wrong for lying . . . but would this be considered cheating in any way? — Tennis-Playing Sugar Baby

It depends on what your definition of “cheating” is, but, regardless of whether you or your boyfriend call it cheating, what you’re talking about doing is deceitful and sneaky and those aren’t qualities and issues you should be introducing to a relationship that you hope will be life-long.

And let’s talk about this idea of a life-long relationship with your boyfriend. You say you eventually plan to marry him, but what’s your plan if your boyfriend continues not to “spoil” you the way you want or financially assist you the way you need? Even if you fessed up about your sugar baby gig (and that’s exactly what it is, however you want to slice it. A rich man pays you for your company; that makes you a sugar baby), and even if your boyfriend was ok with the situation, you can’t be a sugar baby forever. For one thing, you will age out of the “baby” bracket faster than you might imagine right now. And even before that happens, something else might occur in your life to change your looks and/or your desirability to prospective sugar daddies in a pretty major way (like pregnancy, weight changes, or simply being married). And what is your plan once you can no longer count on making easy money off rich men and your long-term partner doesn’t spoil you or financially assist you the way you want? What are you going to do then?

I bring up these future considerations because they very much affect the decisions you need to make in the present. If your boyfriend isn’t a long-term fit for you, then maybe it doesn’t matter all that much whether your relationship survives your current money-making scheme. Maybe, if it’s going to end anyway because you don’t believe your needs will ever be met, it’s better if you just end it now. Or, maybe, if you don’t believe that your boyfriend will be able to give you the things you think you want, it’s better if you adjust your expectations and re-prioritize the things you’re looking for in a mate.

Regardless, if you DO decide to continue seeing your boyfriend and you DO decide to pursue this sugar baby set-up, you need to tell your boyfriend about it. You need to tell him that this guy pays you to spend time with him and you aren’t intimate with him and he doesn’t touch you, but he does pay you for your company. Maybe your boyfriend won’t care. But I bet he will. And you know why? Because most guys wouldn’t like the idea of another man paying for their girlfriends’ company. It won’t matter that you don’t screw the guy. It will matter that some dude is paying you to hang out with him. And if your boyfriend truly cares about you, he will worry about this guy’s intentions (and you should be too!) — this guy who has a wife but is paying another woman to be his companion. He will worry about him crossing boundaries and touching you or worse. He will agonize over this guy fantasizing about you, picturing you naked (even if you don’t let him see the real thing), potentially pushing you out of your comfort zone and taking advantage of you because he’s paid for you, after all, and because he’s the kind of guy who is used to getting what he wants (and probably used to crossing boundaries, as he’s already proven when he sent you flowers at work).

You know this is how your boyfriend will likely react (because it’s how most men would react), and that’s why you don’t want to tell him the truth. And your withholding the truth makes what you’re doing, or thinking about doing (and have already done!), every bit as dishonest and hurtful and damaging as “cheating.” Because in the end it doesn’t matter if you plan to not allow this man to screw you. It doesn’t matter if you aren’t attracted to him and that you’re only using him for his money. It doesn’t matter how innocent you make your arrangement seem (“It’s just tennis lessons!”); as long as you keep it a secret from your boyfriend, you ARE a cheater. You are cheating on the basic rules of a relationship, which include being fucking honest about shit, especially shit like getting paid to be some dude’s companion.

So, be honest. Be honest to your boyfriend, and, God, be honest to yourself.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Avatar photo something random says:

    Don’t feel good about “helping this guy”. He isn’t listening to your advice, he’s trying to establish intimacy and hoping he will grow on you. He’s banking on you hitting the skid with you boyfriend and being that sweet paternal figure that knows the real you.

    And that easy money, he’s giving you? It belongs to his wife and kids. If she ever wakes up and sees her sleazy husband for what he is, half of it is HERS. You are taking money from a family not just a bachelor.

    Also, Why can’t you just give tennis lessons for real (to other people)?

    1. Avatar photo something random says:

      Also, you say you ended the sugar daddy relationship because he “crossed the line and sent flowers while your boyfriend was there”. What if your boyfriend hadn’t been there? Can you honestly say you would have ended things on your own? I ask because you seem to have a really hard time with the concept of boundaries and how to enforce them. I hope you don’t think I’m trying to rub dirt in the wound. I honestly think it might be something worth thinking about.

      Other evidence of this is you guys coming up with a “brilliant plan” after the relationship ended. Clearly you were still in contact. When you decide to end a relationship with someone you put up boundaries to protect yourself. You don’t seem to do that.

      Presumably your pregnant sister is an adult. So is your mom. If you are putting your personal relationships at risk to try to score easy money to help them, stop. It isn’t a healthy dynamic. Poor boundaries don’t just hurt one person. You are also limiting your mom and sister from being healthy, autonomous adults by enabling them. Learning how to be a healthy adult means learning to know and respect your own personal limits. I suggest you explore why you feel uncomfortable putting up safe boundaries. Do you generally have a hard time saying “no” to people you like? Why does helping others justify ignoring yourself? What do you get out of “helping” these people. Can you honor that part of yourself in a way that isn’t so unhealthy?

      Wendy gave you some kind, compassionate advice. I hope you listen to it and really look at yourself honestly.

      1. I actually was looking for a way out and he gave me one.
        We actually didn’t talk for a while.
        But he sent me a message this month just basically telling me that if I wanted the arrangement could be back on just with a snap of my fingers.
        My pregnant sister is not an adult. And it may be unhealthy but it worked.
        I don’t hardly ever tell people no unless I really don’t feel like doing whatever they need me to do.
        It makes me happy to help other people though. I feel like we spend our whole lives searching for purpose and that is one of mine. I fill fulfilled in helping other people even though it might put a strain on me financially, emotionally, or physically.

      2. Avatar photo something random says:

        You should not have felt you needed to look for a way out. You should have been able to end it anytime you felt it wasn’t good or healthy for you.

        It is very kind of you to want to help you sister. But if you hadn’t stepped up, the world would not have exploded on her. She would have found another way. I’m glad it worked out for you this time. But taking on another persons problems as your own may end up sabotaging you down the line. This does not mean I don’t think you should be a loving, giving, person. But you shouldn’t give more than you have to spare.

        You really do sound like a well-intentioned person at heart. But your actions sound hurtful to your relationship and your boyfriend. Having good intentions at this point would include learning something from your mistakes and not making them in the future. You seem to be in this process now.

    2. I did feel good about this guy.
      I’m not trying to defend myself but I’m smart enough to know what I was doing.
      And I did it well.
      The majority of the time we hung out was discussing his wife and children.
      And I did help him. I got his to see a therapist. I got him to try and fix their marriage problems.

      1. Avatar photo something random says:

        It sounds like you felt good about your interactions during your time with guy. We all have the power to influence each other but adults only achieve major, lasting change from the inside out. Its nice that you told this guy to see a therapist and he told you he did so (implying it was because of you). But you do seem overly-trusting about this guy’s intentions. This does not mean I think you stupid. Perhaps you don’t have any practical marital experience. Him talking to you about his closest feelings and relationships would not be considered therapeutically appropriate. From his spouses perspective, it would most commonly be considered a serious violation of trust. This guys behavior escalated, did it not? With the flowers? and if several months later he wants to pick right back up, chances are his marriage isn’t getting better. This is not your fault. Nor would it be your accomplishment if it did seem to improve. Learning this has been an ongoing lesson for me in my own life. You really can’t fix others, they have to want it for themselves.

  2. Yeah, this set up isn’t ok. You need more money? Get a second job. Don’t financially help your mom start her business. Be emotional support for your sister but tell her you unfortunately can’t help out financially. I know you want to be everything for everybody, but if you can’t afford it and you don’t have the money for it then DON’T fork over money for expenses besides your own. Focus on supporting yourself. Focus on your own budget. Cut the unnecessary expenses, and stop seeing this guy entirely. You may not have a physical relationship, but it’s still cheating.
    I’m also kind of sickened that you don’t think your boyfriend “spoils” you enough. Is he a good boyfriend? Does he treat you well? If the answer to both of those is yes, you already have a better boyfriend than half the boyfriends we hear about here on DW. Quite frankly though I don’t think he deserves YOU.

    1. Avatar photo something random says:

      I thought that “spoils” comment was nasty, too. It’s so old-school patriarch rewarding the pretty/sweet/compliant little woman -esque.

      Be a strong, Independent woman. Wasn’t there a Destiny’s Child song about that?

      1. It’s horrible. My boyfriend treats me well and he respects me. He’ll make me coffee in bed sometimes, or help me out with my dishes or something, but it’s like this LW is EXPECTING financial assistance from her boyfriend. Not ok.

      2. “spoils” is a word that doesn’t adequately describe what I would like in my relationship.

        My boyfriend is a spoiled rich boy who has always had a maid.
        I come from a lower to middle class family and have worked hard for everything I own.

      3. But it is the word you used.

      4. I was trying to keep it short and sweet.

      5. I don’t know if you have all that much respect for your boyfriend. I’m really not trying to be mean here, but you call him a “spoiled rich boy who has always had a maid”. I get that he grew up in a better environment than you did and you work really hard for what you have but that doesn’t mean that he owes you anything financially.

      6. Avatar photo something random says:

        Thank you for clarifying this point. You can see how using this language triggers a lot feedback. I think it didn’t help that the last letter writer hadn’t supported herself in eight years. You may have inherited some of the blowback from that.

      7. spolied is not good. I had no money from anybody. I did marry but quickly realized i needed an edu so I took out grants received a college edu while rasing children. Only to have money going to something like this feeling sorry for the pretty poor girl while the wife is and had worked her self to death to manage . I say get an education it last longer. From experience looks will always fail . But if you have cash for surgery your in luck. But men come and go so edu yourself and be happy for you.

    2. Also…a man is NOT a financial plan. YOU are responsible for that for yourself. It is the 21st century, time to act like it.

      1. Avatar photo something random says:

        Well said! We need a Dear Wendy mug that reads A MAN $ NO PLAN.

      2. I wasn’t searching for a financial plan.
        I was searching for help.

      3. Sorry but I think you were looking for “help” in all the wrong places. Start with yourself — focus on what YOU can do to improve your situation. Budget and cut what is unnecessary. That’s the first step.

    3. Family is family. You do everything you can for family. I believe that with all of my heart.
      I have three jobs actually. I work very hard for my money. Sd offered a little assistance.
      It’s hard to understand me and my family’s situation. And since I am not friends with all the people on here its easy to look at this from the outside and give advice.

      My boyfriend is wonderful. Everyone has their downfalls.
      And sometimes its hard when you go all out for his birthday and for yours he forgets.
      Sometimes I feel under appreciated but that doesn’t change the fact that I love him.
      Your right I probably don’t deserve him.

      1. I really do get that and I understand that. I’m sorry that you’re going through a rough patch — I know all too well what it feels like to not have enough money for bills. The fact is that you can’t afford to financially support your family members. I know you want to –trust me I get it — but you HAVE to put yourself first. By all means, be for your family emotionally, mentally, and spiritually. But if you can’t pay your own bills, you definitely can’t afford to pay your family’s bills. If your mom can’t afford to start her own business, quite frankly she should be looking for a job of her own. That’s on her. If she wants to start a side business while working and being able to pay her bills then great! She should do that if she can afford it. It’s financially irresponsible to start a business you can’t afford.

      2. I’m legitimately not trying to be mean here, but does your mom know your financial situation? Does she realize that you’re giving her money you don’t really have? If she does and she is still letting you support her, she’s being pretty damn selfish. If she doesn’t know, tell her. Sit her down and tell her that as much as you would like to help, you can’t afford it right now. If your family is as close as you say she will understand and she will expect you to take care of yourself first.

      3. Avatar photo something random says:


  3. Avatar photo something random says:

    (Somewhat Unrelated) Does anyone watch Amy Schumer? She has the funniest skit about Maria Kirilenko. That’s the girl in the picture, right?

    1. Avatar photo something random says:

      I may have had too much coffee this morning.

      1. Avatar photo Addie Pray says:

        haha, wait for me! I’m only on my first cup. though i’ve been up since 4 am. (stupid day light savings; it only means people like me who wake up naturally at 5 am are now waking up at 4 am.)

      2. RedroverRedrover says:

        We just got our baby sleeping till 6, and now he’s back to getting up at 5. 🙁 Why can’t we get rid of daylight savings already?

    2. Avatar photo Addie Pray says:

      i’ve seen some of her stand-up routines on youtube and thought they were awesome. i’ve seen a few episodes of her show but just thought “meh” though.

  4. Avatar photo fast eddie says:

    No matter what you call it, your taking money and giving a service. Nothing wrong with that oldest story in human history, but the boyfriend is your dirty little secret and all three of you going to be hurt by the arrangement.

    1. SD knew about my boyfriend. He knew he couldn’t come between us and he respected that.

      1. Avatar photo something random says:

        You thought that. Can you honestly say that is the case after the flowers? You don’t need to defend yourself again. Just think about it.

  5. Avatar photo Addie Pray says:

    Oh for Pete’s sake. Barf. There’s been a theme with these LWs lately. … But I’d just like to say how impressive it is when Wendy is able to give good advice to certain LWs without judging. That would be hard.

    1. Here’s some judgment: Sugar daddies and sugar babies is one of the most repugnant tropes in modern society. Prostitution is what it is. It is simple and doesn’t pretend to be other than what it is. I object to the commodification of human intimacy on aesthetic and romantic grounds, not moral. But the commodification of “relationships” gives the lie to everything I want a human relationship to be. The idea of expecting to be pampered and spoiled instead of being responsible for your own development into a worthy human is just sad. The idea that someone else should pay you for the privilege of your “company.” That your transient and superficial “hotness” should be not only the way you make your living but how you define yourself. LW, I actively avoid people like that. Hats off to Wendy for her fair-mindedness, and I’ll understand if she thinks this comment is too judgey and deletes it.

      1. I like that you are very opinionated.
        I wasn’t making money off my “hotness” I guarantee that.
        I was making money off of a lonely sad married guy who lost interest in life.
        I was making money by telling him what I though about his current situation and giving him a friend to talk to when things weren’t doing so well.

      2. Avatar photo Addie Pray says:

        “Making money off a lonely sad married guy” … this is a good thing?

      3. If you could help a person like that than I say yes.

      4. I disagree. It’s parasitic.

      5. How?

        I am a firm believer in creating a better world.
        I’m also human and I am still learning from my mistakes every day.
        In order to create a better world you need to start with the people. One person at a time. That means lifting people up and helping them instead of alienating them to their own problems.
        Everyone needs help in one way or another. And if I can help someone out I will, and hopefully inspire people to do the same.

      6. Then do it for free. Or become a professional therapist. That’s what this guy needs. Look, all I read in your letter was how it was easy money. That sort of belies any altruistic motive.

      7. Avatar photo something random says:

        Lifting people up and helping them is only something you can do for those who want it. Yes, everyone needs help in one way or another. I truly believe aren’t in a position to help this man in a way that would really impact his life. If this guy wants to fix his relationship or become a happier person that are better channels out there. The “help” he is requesting is inappropriate assuming you want a healthy relationship. There are men that wouldn’t mind if you decided you really wanted to work as a sugar baby. Your boyfriend doesn’t appear to be one of those men. If you want to create a better world it starts at home.

      8. You helped him for your own benefit, not to “change the world.” From all of your comments on here there’s no way you could ever get me to believe that you helped him because you wanted to.
        And for the record, if you did not have a boyfriend, I wouldn’t think what you were doing is wrong. It’s the fact that you are in a committed relationship, that is serious enough that you want to marry him. That’s what makes all of this wrong.

      9. Avatar photo Monkeysmommy says:

        Okay, I have read as much as I can without chiming in. LW, like many LWs before you, you have written in asking for advice on a situation that you have no intentions of changing. You just want everyone to go along with you and tell you that you were doing the right thing, that there is nothing wrong with your current situation. I am not going to do that. If you need financial security, then you either need to get a job that pays more, or you need to stop helping and overextending yourself. Who cares if your boyfriend is a spoiled rich kid? The fact that he has money does not entitle you to one penny of it. He is not your husband and is not responsible for keeping you up financially. As for this poor sucker that is paying for your time, his money would be better spent lavishing attention on his wife and children. You better believe if I found out that my husband was spending his money on some little floozy who claim to be doing me a favor by helping him work through our marriage,there would be hell to pay for both of them. I don’t care how good of a person you think you are being by trying to help your mother and sister, all of that is negated by what you were doing to this man’s family. Are you a fool? Are you really that stupid? You really think this man does not want to get in your pants?? That he will be happy with just paying for your attention forever? Get real. He is working you like a job, ha ha literally, to make you see what a sweet and understanding person he is, unlike your boyfriend, so he can get a piece of that.I know, I know, we are all just old and jealous right? We just don’t understand your life, right? We just don’t know how hard you have it? Again, get a reality check. Everyone has problems. Everyone has struggled financially at some point in their life. You don’t see us cozying up to married man begging for a handout. If you really want to make money off of man, take up stripping.

        Geez, I’m really judgy today!

      10. IF I was the wife I would be furious with my husband. Its not the LW who is doing something to this man’s family, it is the MAN himself who is choosing to go outside his relationship. Really! He is making that choice & if it wasn’t this LW it would be another woman. How is this the LW’s fault?

      11. It’s her fault as well as his because she is participating as much as he is. She knows he’s married, and despite what she might say, she knows darn well what he hopes to get from her.

      12. HIS relationship is not HER responsibility. She is wrong because she is also in a relationship, but what he does to his wife is between him and his wife, not this LW.
        I don’t undertand why we are so quick to react and judge “the other woman” when they’re hooking up with someone that is in a relationship. Some people have morals and can’t do it, other single people see it as NSA hook ups. If HE wants to cheat on his wife, that’s between them.
        Again in this scenario it is wrong because they are both in relationships and even if they weren’t physical there is an emotional relationship that is building.

      13. We just need to agree to disagree. To me, NSA means no boyfriend, no spouse, nothing. If a woman helps a man cheat on his wife, she’s as guilty as he is, IMO.

      14. All sex work (to use an all encompassing term) is about the commodification of relationships to a degree. It’s the human condition. I was once a stripper and I wasn’t making money because I had a hot body, and I definitely wasn’t doing any extras. It’s not that hard to find someone with a hot body. I made money because I engaged with customers and developed relationships with them. I made money in the VIP room to simply talk and have a private conversation, albeit at a very expensive rate. It’s really not that different from a sugar baby relationship. I also had a loving boyfriend who supported my choice.
        Many people would rather have a friend with benefits or ongoing fling than multiple one night stands to get laid. There is also a relationship and intimacy aspect there. FWBs are “paying” each other for the company.
        I’m not defending this LW in particular, but to call sugar daddy/sugar baby relationships repugnant is ignorant at best. You don’t have to like it, but Instead of actively judging women who partake in such activities, maybe you should judge and avoid the men who create these opportunities in the first place.and they’re definitely not who you would expect them to be.

      15. Avatar photo Dear Wendy says:

        I agree with all of this.

      16. Well said Mylaray …. I feel like the LW today is really getting beat up. Her story as presented is…. well, I can see how it opens her up for judgement shall we say? However, we all know that 3 paragraphs in an advice column can in no way encompass everything that went into this situation, nor do we know what kind of person the LW really is. I choose to err on the side of compassion. We all have things we are less than proud of, but it doesn’t mean we deserve harsh condemnation. LW I think that your intentions were good maybe, but if you truly love your BF & see a future with him you need to sort out your values & be honest with him. If your values don’t match up, then he isn’t a good fit. When it comes to opinions on whether this is cheating or not, his is the only one that matters. Relationships built on deception are not strong & lasting.

      17. RedroverRedrover says:

        I think if you want to do sex work, then do it. I personally think it should be legal. But what you should not do is try to paint it as an innocent friendship, as an excuse for not telling your boyfriend about it. That’s why the LW’s getting beat up, for the most part.

      18. She has stated several times that she has not had sex with him. I’m sure the older guy would LOVE to have sex with her, but she hasn’t done it. Its an emotional affair, & she was asking if that is considered cheating. I happen to agree that it is. But there is still such a thing as compassion & respect, & the tone here today is far from either of those. We are better than that. Just my opinion….carry on.

      19. Agreed. People are arguing about semantics and word choce when she already refers to herself as a sugar baby in her letter, and telling her to own it, comes across as a way to shame her instead. Having empathy is key. Yes, she’s emotionally cheating on her boyfriend and needs to stop that, but it’s clear much of the negative tone here is because of her way of making money. A lot of “other women” get portrayed harshly and it gets taken too far, in my opinion. Where’s all the negativity for the older married man cheating on his wife? Oh, right.

      20. Slut-shaming….. It was an unfortunate choice of words for the signature line, & now she is getting trashed.

      21. Avatar photo something random says:

        I love that this thread is still going 🙂
        @mylaray, if the older married man cheating on his wife wrote in, I have no doubt there would be much harsher comments for him. My understanding of professional sugar babies is that they have they go in with intentions and boundaries in place and up front. While this lw might technically be a sugar baby in that she is pampered in exchange for companionship, I don’t really think of her as a professional in this situation. If that were the case she wouldn’t even need to question whether there is infidelity within her own relationship. The details of how she met this guy and what the agreement was and how it came to be are all a vague. People are inferring what they can. And I don’t think this is slut-shamming. Nobody is bringing up the letter-writers sexuality at all. They are bringing up the morals or lack of morals associated with dishonesty and or infidelity (not only from the perspective of the married man’s family, but also from the lw’s own boyfriend). Yes, some of the response and judgments are harsh. But I think that is to be expected when discussing such a triggering topic.

        FWIW, I don’t think most of the sex industry is empowering to women and I own that as my personal bias. But my distain is not for women choosing to use their own bodies to make money but rather the industries that fail to protect women from disease, harassment, and abuse while taking exploitive cuts from women with low bargaining power. I don’t think this bias applies to this letter because I don’t actually see this letter writer in the sex industry.

      22. This is exactly why I commented. I agreed with the general advice (be honest, examine boundaries, what are you exactly looking for out of this, etc), but the tone in the comments was making me angry. Even Wendy’s whole paragraph about the boyfriend’s possible reaction, like another guy is picturing you naked? You don’t need to be a sugar baby for that to happen, I could be thanking the guy at Starbucks for my latte and that could happen.

      23. I’m not really sure why you think I am judging women but not men here. I’m also not sure why you think I am ignorant. I’m not. I’m well aware of all of the permutations of relationships that you outline. I don’t partake in any of them. i’m aware that you are likely to say that this is easy for me to say, being long married, being male, reeking of privilege, etc. I also highly doubt that you paint what you do as anything other than what it is – a business relationship in which each party benefits, one with services, the other with cash. As i said, i don’t object on moral grounds. But i am a romantic. Perhaps I am lucky, but i also invested heavily in the kind of love relationship that would make me happy, one that was based on equality, mutual love and respect. I rejected opportunities to do otherwise, and there have been plenty. The one time I was in the presence of a stripper, at a stag for a former male friend, I found the unequal power dynamic in that basement rec room horrifying, and I left. The friendship ended soon after, and the marriage only lasted a couple of years, due to the groom’s unsavoury attitudes toward women and fidelity. (I understand that after I left, several guys there, including the groom, had sex with her. Ugh. Gross.) Mylaray, i would never judge an intellectually honest person for choosing your way of making a living, even though I would not personally be interested in buying the product. But i don’t think that describes the LW here. you and I may disagree about the expression of physical love, but I think you are mistaken to call me ignorant. i simply don’t see the world and relationships as you do.

    2. Avatar photo Dear Wendy says:

      Sometimes there’s some judging. I’m only human.

  6. It’s kind of sad that you had to come up with a plan to make yourself feel better about what you’re doing. Does it matter if Wendy or someone else thinks it’s cheating if it makes you feel crappy to do it? Wendy’s advice is spot on and a lot nicer than anything you’re going to read from anyone else.

    1. I completely agree. I didn’t say I didn’t feel bad about it.
      I probably felt the worst I ever had, but it wasn’t a question of right or wrong. It was a question of was it deemed cheating or not? In my opinion cheating is having either romantic or sexual relationship with someone. Both of which my situation was neither.

      1. And my comment still stands if you feel crappy about it does it matter whether or not it’s cheating? If you can do it and not feel bad about it there is no problem. If you feel bad about it then there is probably a problem.

      2. That’s the part that gets confusing.
        The reason I felt so bad was because I could have been spending quality time with my boyfriend instead of trying to help a grown man with his own problems.
        The other reason I felt really bad was because I knew that if my boyfriend would ever find out or if I would tell him I don’t think he would believe that I didn’t have a sexual relationship with this guy. He wouldn’t believe me. And I cant blame him for that. But knowing any second I could lose him made me sick to my stomach. That’s why I wont do this again. Even if I could get away with giving tennis lessons and still being able to make a little extra money.
        Nothing is worth losing him. It just took a little while for me to realize that hard truth.

  7. Really? I see how this could go bad and she needs to protect herself and make sure she doesn’t put herself in a dangerous position (meet in public places, for instance, maybe make sure someone knows where you are). And it needs to be clear that he can’t encroach on her real life. And probably not lie to the boyfriend about it, because people shouldn’t lie to their significant others. But it doesn’t sound like she’s cheating on her boyfriend. And if they only meet on the tennis court (which as a former tennis player I assume to be very public at any club they go to), I see no real harm. Models get paid for their looks, psychologists (and case workers and others) get paid for talking to people about their problems. It’s not a standard and socially-acceptable form of service work, but it doesn’t seem to me as much like prostitution as the rest of you all think. Unless she feels indebted to him in some way and is guilted into doing more than she’s comfortable with. But that happens in regular relationships and is not sugar daddy-specific.
    The problems I see with this situation echo others, though: that she’s looking for a man to support her (be self-sufficient!), lying to her boyfriend, not able to set strong boundaries, and being a little too materialistic. But that would be the case without this sugar daddy business. But it sounds like even if she leaves this current situation, her priority would be to find a romantic partner to support her financially and it’s not really better to choose a boyfriend because he will support her financially, right?

    1. RedroverRedrover says:

      She didn’t go into it much, but I’m assuming they’re “dating”. Going out together, he pays, he buys her gifts, etc. She says he’s married and looking for excitement, so clearly she’s offering something. She must be flirting with him and letting him treat her as if they’re a couple, in public, even if it’s not physical. Because otherwise, what is he paying for? He could easily go to a psychologist if that’s what he wants.

      1. I really just don’t see it as so much of a departure from other service jobs or other things people do for their work. For instance, during my fieldwork, I was overly friendly, used some flirting-like behaviors, got people to talk about whatever they wanted to talk about, etc. And it allowed me to amass way more data than someone who wouldn’t kind of play the game could do. I even discussed my interviewing with someone at a recent conference because he (as a very opinionated gay man) was not having luck with his fieldwork and most of it came back to the fact that he wasn’t going about it in the same way.
        Another academic friend interviewed someone the morning after sleeping with him. I don’t think that makes him a prostitute…
        I do agree that she should be above board with her boyfriend. But I don’t find what she’s doing inherently wrong or cheating.

        In the topic area of hiring people for unconventional service jobs, I also have been watching a lot of old House episodes recently and find the kinds of interactions he has with women he hires fascinating.

      2. RedroverRedrover says:

        I think the fact that she thinks it’s cheating, means there are behaviours going on that would probably be considered cheating by her boyfriend. If it crosses the line of what they agreed to as a couple, it’s cheating. If she’s dating another guy for money when they’re supposed to be exclusive, it’s cheating.
        If it had been tennis lessons from the beginning, that would be different. But they have a certain relationship now. It won’t matter to the boyfriend that it’s just tennis lessons now, when it was dates for money in the past, you know what I mean?
        In short, I don’t think she’d be asking for advice if she felt good about this and that there was nothing wrong with it. She’d be able to just tell her boyfriend what her job is and leave it at that. If she thinks her boyfriend will be upset with what she’s doing, then it’s probably out of bounds of a monogamous relationship, which I’m assuming they have.

      3. I think we’re reading different things into the guilt she’s feeling. I’ve had friends feel guilty for the most harmless stuff, and not feel guilty in the slightest for things I can’t imagine doing. Think about accepting a free drink at a club while you’re monogamous with someone. Some people will feel guilty and not accept it. Others will feel no guilt and accept it. It’s the same act, and some significant others would take it as not cool and others would be totally fine with it.

      4. RedroverRedrover says:

        Well, like I said, the only person who will know if it’s cheating is her boyfriend. Maybe he’s ok with the idea of her being a date for hire. Who knows? Regardless, she has to tell him and deal with the fallout if there is any.

      5. Avatar photo something random says:

        I don’t think being personable and good at your job is comparable here.

      6. And my friend was just really good at his job and personable when he slept with that guy he interviewed… I’ll let him know the moral police won’t be knocking down his door for that.

      7. Avatar photo something random says:

        If your friend gave preferential treatment to the guy he interviewed over candidates that didn’t elect to fuck him then I do think it was wrong. There are no moral police because morals are self-imposed constructs. I happen to think giving preferential treatment in exchange for sexual favors is an abuse of power. But I don’t know what was in your friends heart and head.

    2. Other types of jobs that are not long term plans but the moral police would not jump all over: football player, modeling, adjuncting. I’m sure I’ll think of more in my meeting…

      1. I imagine not a lot of football players get flowers sent to them at work and they don’t hide what they do from their partners. I think people are objecting to the deceit aspect and the attempt to ‘put lipstick on a pig.’ You can dress it up in how may ever tennis skirts you want to but she’s essentially an escort.

      2. No, but I imagine the more attractive football players get sent panties. I assume something like that they’d hide from their partners.
        I’m also objecting to the deceit aspect, but it really does sound like the moral police around here today. Which is fine, everyone has their own opinions, mine is just different.

      3. I’m guessing the people paying them aren’t the ones sending the players panties! Otherwise I’m looking at those old, white men a lot differently after today.
        And that is the point here… Getting paid to do a certain type of work. And if that work is, at the root of it, legitimate. I’m personally torn – I feel that women should be allowed autonomy over their bodies and lives to do whatever they want with them. But so much of the sex trade is truly not consensual and it isn’t a environment that empowers women – it subjugates them and traps young girls as essentially sex selves to their pimps and objectifies women as objects that bleeds over into the rest of society. But if that is the life you choose – then so be it. Don’t obscure your paid companionship as tennis lessons in an attempt to deceive your boyfriend. If you are big enough a girl to work in that field then you are big enough a girl to own it.

      4. Avatar photo something random says:

        Football players, models, and adjunct faculty can all put that on a resume so I do think they are investments even if they are short-term careers. I actually do have some ethical reservations about professional football players by the way. Even a professional escort could potentially dress it up and put it on a resume. Secretly re-establishing a relationship with a married man that you know is actively pursuing you because he continues to give you presents in the hopes of something more is something else. Helping him with his uh stroke might not be overtly cheating in her mind but it probably is in her boyfriends mind. Only one person has to think of it as cheating and make it clear it’s a boundary-violator for it to be so.

      5. Avatar photo something random says:

        And adding a cutesy name like “sugar baby” doesn’t make things any more innocuous.

      6. I really didn’t know what else to call it. That essentially is what this is. Is it not?

    3. But, she feels kind of crappy doing it and it sounds like she needs someone to say no of course it’s not cheating. Does having someone not in your relationship say that actually make it better? If knowing yourself and your relationship you do feel bad? That and assuming she’s going to lie to the bf about it, making it seem like a job when it’s really just a way to get around hanging out with the guy without him knowing. I don’t think it’s as cut and dry as a single person or a person with a partner who is on board with it, being in this situation.

    4. I really liked that you looked at my situation different than the rest. So for that I thank you.
      I am not looking for a man to support me. I support my self. Let me clear that up right now.
      I work three different jobs and spend the majority of my time working.
      With my money, yes I do help my sister and my mother. Because that is the right thing to do.
      All I was looking for was a little help. The money I received didn’t go to buying new clothes and shoes. It went towards bills and food.
      I am not looking for a romantic partner to support me. I love my boyfriend the way he is.
      It be nice you know to get flowers every once in while or take me out.

      I feel like the only thing I am guilty of is lying. Feel free to disagree.

      1. RedroverRedrover says:

        “I feel like the only thing I am guilty of is lying”
        Unless your boyfriend would consider what you did to be cheating. If he would, then you’re guilty of cheating on him, too.

      2. I’m not sure.
        If I told you I went for drinks with a friend of the opposite sex and that’s all that it was and I was accused of cheating, would that be cheating? Just because he thinks that it is?
        This is the problem that I am having.
        I didn’t have a romantic or physical relationship with this guy.
        He paid me essentially for my advice and the ability to look at his issues from a different perspective.

      3. RedroverRedrover says:

        But what exactly was your agreement? You call yourself a sugar baby. Are you saying that this guy hired you as basically a therapist? Or did he hire you as an escort, even though you made clear that it wouldn’t be physical? And if it was the former, why would you consider yourself a sugar baby, and why would you be worried about what your boyfriend thought?
        I don’t know, if my husband came to me and said he’d been going out for drinks with women for money, I would consider it cheating. It’s not the same as going out with a friend of the opposite sex, and you know it. For one thing, friends of the opposite sex don’t pay you for your services.

      4. Any relationship where one party is plying the other party with gifts and flowers, in an attempt to please, them is a romantic one. Being willfully blind does not change the truth of a situation. Why do you think the old married guy is giving you gifts and money? Are you a psychologist? a psychiatrist? marriage counsellor? Do you have a fee schedule and an office? Or are you pretty? And he likes spending time with you? Prostitutes say 90% of their work is just listening to the John. Stop trying to spin everything. You traded companionship for money. You call yourself a sugar baby – a sugar daddy/sugar baby relationship is a romantic one – even if the primary motivation is financial for one party. Unless you see something wrong with that – why not just admit it?

      5. I also think you needed to set stronger boundaries with that guy.
        Anyway, since you’re not planning to get back into that financial arrangement anytime in the future, my advice would be about your current relationship. I think you need to have a discussion with your boyfriend about the types of demonstration of affection you say you want, like flowers and dinners. If buying you gifts makes him uncomfortable, make it clear you want him go do things that let you know he’s treating you in some way. Make you dinner? A hand drawn card? Your favorite type of chocolate? This may stem from a love language mismatch type of thing and I think you should explore it with him instead of looking for it elsewhere. Also, don’t give money to people if it’s beyond your means. It sucks to not be able to help out people you love financially, but it happens. Focus on what you can help with instead: doing chores, running errands, making them food…

      6. Thank you! This advice I will follow!

  8. RedroverRedrover says:

    Aw, your boyfriend doesn’t offer you financial help even though you really need it? Well, welcome to the real world. No one owes you anything. Time to take care of yourself. If your job is that you’re a plaything for rich old men, then be honest about it. And even though it’s not technically prostitution (yet), it’s thisclose and you’re fooling yourself that it’s something innocent.
    And stop expecting men to support you through life. You’re an adult (presumably). It’s no one’s job to support you but you.

    1. I do support myself. I am very aware of the world I live in. And I do not consider myself a “plaything” for older rich men.
      I am a firm believer that every situation is different. The problem is that all situations get “grouped” together by judgmental non-understanding people into categories they don’t fit into.
      How can you or really anyone give a biased opinion if you haven’t experienced or known someone that has experienced a similar experience?

      1. LW , coming from someone in a swinging relationship, here is my & my BF’s rule for whether its “cheating” or not. If its just sex, its not cheating. Drinks, dinner, hanging out, texting, calling, movies, etc is a no-no, its more like emotional cheating, or maintaining another relationship outside of your primary relationship. Its taking away time & focus away from the one you love. I realize your situation didn’t involve sex, but it was still developing a relationship away from your BF. So in that sense, it was kind of cheating, but everyone makes mistakes. I did it myself, & once we talked about it & I understood how that made him feel, I resolved to never let it happen again. And it hasn’t.

  9. Call a spade a spade. If you want to be an escort – be an escort. Some escorts don’t have sex – they just provide companionship – for money. Which is what you are doing. If you think your boyfriend will object to your side business of being spoiled by old men you spend time with for money – whether or not you carry around a tennis racket – then that is a risk you take. I imagine most boyfriends would be upset if their girlfriends escorted old men for money – on or off the court. Get another job if you want to keep the boyfriend – oh and lose the attitude that men are supposed to spoil you and shower you with gifts. You aren’t a two year old that someone should be catering to and showering you with sparkly things just because you are cute. You are a grown ass woman and there should be a hell of a lot more to you than that.

    1. PLease read the other comments I left.
      I promise I’m not a spoiled brat.
      I just would like to feel appreciated every once in a while.

      1. Avatar photo Crochet.Ninja says:

        then you’re with the wrong bf. if you feel like you have to go outside of your relationship to be appreciated, MOA – for yourself and him.

      2. Not every relationship is perfect.
        It takes hard work.
        And I guarantee not every guy or person for that matter is perfect.
        I love my boyfriend.
        I don’t need to look for someone else
        Because I know that If I did happen to find someone tat wanted to spoil me rotten they would be lacking in other areas that are essentially more important

      3. “I don’t need to look for someone else” … But you did, hence the letter you wrote in asking for advice. You weren’t getting what you wanted (attention/appreciation) from your boyfriend so you found an old man to give it to you. That is looking AND finding someone else.

        If you were your boyfriend in this situation, how would you feel?! I bet you’d feel cheated. I’d bet you’d feel deceived and lied to. Think about how you’d feel if you were him and that should answer any question you have.

      4. THIS! If your needs aren’t being met, it’s time to MOA.

      5. Feeling appreciated and being ‘spoiled’ are not the same things…maybe with another boyfriend they might be but not with the one you have and not with one worth having. That he doesn’t spoil you isn’t a reflection on him…that you would want/expect it is a reflection on you.

      6. You are absolutely right
        And I am trying to work on that

  10. TheRascal says:

    Oh for crying out loud. You are being dishonest and selfish. How about you break up with your boyfriend (because you are lying to him) and you ditch the old guy. Take care of yourself for a while and try to figure out why you think being a liar is okay.

    1. I never said being a liar was okay.

      1. TheRascal says:

        Your actions say differently. You are being dishonest with someone that you say you love. And you are okay with it, as long as it isn’t “cheating.” So, you are lying. And you think it is okay. So you think being a liar is okay.

      2. No I think you are putting my words in to an equation. Its not that simple. Most things rarely are.
        I am lying to someone I love. And I am by no means okay with it.
        I didn’t right this piece to figure out if I am wrong or not
        I wrote it because I wanted to know if it was deemed cheating
        lying and cheating are not one in the same
        they mean and are different things

      3. TheRascal says:

        You are correct that lying and cheating are not the same thing, though they are not mutually exclusive.
        And honestly, who cares if this is “cheating.” Lying about a secret relationship is just as bad. You lied and continue to lie. You are untrustworthy.
        I will tell you this: if you are uncomfortable with your boyfriend knowing of your secret relationship because you believe he would be hurt….why do you think he would be hurt? Is it because you are sharing a closeness with another man without his knowing? Is it because you are being paid to do this? Why not just be this older man’s friend? Why do you have a problem with that, if this older man is someone you truly want to help?
        You have acted in a manipulative way with the older man, exploiting his emotional situation. Then, you justify it by claiming how benevolent your for-profit actions are.
        I think you have a lot of soul searching to do. If you are not okay with lying to your boyfriend THEN STOP LYING TO YOUR BOYFRIEND.

      4. I would actually be more forgiving if my boyfriend cheated once – i.e., a one night mess up – than if he continually lied to me about what he’s doing or who he’s hanging out with or what he’s getting paid for or where that new cologne came from.

      5. LW, in my relationship, if I am dealing with someone and feel uncomfortable telling my spouse, I don’t do it. If I have to say “Is it cheating?” I don’t do it. You need to decide if you love your boyfriend more than the money and if he loves you enough for you to give up the money.

  11. I have nothing else to say, really, except this: LW, if I were your boyfriend, I would run far, far away. I would not marry you. You lie, you cheat, you’re a potential home wrecker, and in addition to not enforcing boundaries, you don’t have your boyfriend’s best interests at heart. He sounds like a good guy. When he discovers your little “arrangement”, do you stop? No. You find a way to continue doing it even though you know it’s wrong. You’re not fooling anybody with that “tennis lesson” schtick. It’s not brilliant, it’s pathetic. Grow the hell up.

      1. You’re welcome.

  12. Avatar photo Crochet.Ninja says:

    you’re already cheating. i’m assuming you haven’t told your boyfriend about this guy – because you feel guilty. and you should.

  13. Avatar photo Dear Wendy says:

    No one has commented yet on the stock photo I used? You should have seen the selection for the search term “sexy tennis.” I COULD have used a picture of a woman wearing a bra and panties and thigh high pink fish nets, holding a tennis racket, but I didn’t (nsfw?). You’re welcome.

    1. RedroverRedrover says:

      … kind of disappointed now. 🙂

  14. Hey Wendy and the people who commented on this post,

    Thanks for your brutal honesty lol.

    First, let me say that there is a lot more to the story. (AS THERE ALWAY IS)
    All in all you guys are completely right and I did not disagree with anything you guys said.
    I know I am wrong in this situation.
    I did this because I felt in control of the arrangement so to me it was perfect way to make money as long as I was in control of the rules.

    Second I don’t plan on setting up our arrangement again. The way I felt in this arrangement was indescribable and I don’t wish it on any human being. I know he wanted to sleep with me and I did set up boundaries. I helped this guy get to the root of his problems. He actually had slept with other women and nothing made him feel better.

    He didn’t come to me because he hoped that one day something might come out of it. He knew about my boyfriend and why I was doing the things I was doing. And he respected me and listened to my opinions. In addition he tried some of my “crazy” new age rituals to try to make things work with his wife. I even made him right a letter to her to try to spark up their love life.

    My intentions in all of this were very innocent, however wrong I may be.

    I’m aware of what I did and how that might impact me and my boyfriends future together. I do regret not telling him, but I’m not sure I regret befriending this guy. I feel like I impacted his life in a positive manner. And he helped me when I really needed it without degrading me and making me feel worthless.

    I’m not going to tell my boyfriend about any of this and try to forget all about it.

    Just because he doesn’t spoil me doesn’t mean I’m going to end things with him.

    That’s not what love is. Sure I wish he’d buy me fancy gifts and take me on vacations, but what girl doesn’t? I love him just the way he is and eventually I’ll be able to handle my finances by myself.

    When your working three jobs and trying to eventually finish school, shit gets tough.

    I looked for options and I am lucky to have found an easy way out even though in only lasted a couple months.

    Anyway thanks!

    1. Avatar photo something random says:


      It sounds like you have gotten some clarity. I appreciate you coming back and filling us in with your perspective; it always makes the letters so much more detailed and interesting. You brought up a number of things I may go back and comment on when I have time if you are still interested in debating- (things like what constitutes cheating versus general dishonesty, having good boundaries while being loyal, communicating with your boyfriend, secret keeping, the impetus to do good and make the most of situations versus the umbrella desire to maintain boundaries, The difference between inappropriate relationships and sugar babies) There’s really a ton of interesting topics you’ve brought up. Anyway good luck with everything.

      1. Thank you very much. and I’d love to debate

      2. Avatar photo something random says:

        Okay I didn’t really have it in me to debate but I did respond to some of your other posts. I’m sure reading internet judgements from limited, biased strangers is not easy, especially when they are harsh. I don’t usually bother to get this involved in the comments but overall I like you, letter writer. It takes guts to come here and respond to everyone. I hope you got some clarity and are better off for the collective experience.

    2. LW, I just want to caution you in regards to this older man… you’re being very naive when you say:
      ” I know he wanted to sleep with me and I did set up boundaries. I helped this guy get to the root of his problems. He actually had slept with other women and nothing made him feel better. He didn’t come to me because he hoped that one day something might come out of it. He knew about my boyfriend and why I was doing the things I was doing. And he respected me and listened to my opinions. In addition he tried some of my “crazy” new age rituals to try to make things work with his wife. I even made him right a letter to her to try to spark up their love life.”
      He is not establishing this relationship and emotional intimacy with you because he wants to fix things with his wife. If he were, he would be spending time on repairing things with his wife, and not seeking out ways to get close to you. If he wanted to fix things with his wife, he wouldn’t be seeking out companionship with other women. This tennis thing is just his way of getting you to open that door again, for one sole purpose. He wants to have sex with you. Men like this are not in these types of relationships just for friendship, or just because they like the advice, or just because they like spending money on someone. You need to realize this, and to protect yourself. Don’t be naive. He’s playing the long game on this one, and he does not have your best interests at heart.

  15. The real problem here is the secrecy. I mean, if she had been giving legit tennis lessons to old creepy men in exchange for money, no one would be all like OMG you are exchanging “a service” for money WINK WINK. That’s what we all do at work anyway. But when we start hiding who we work for from family and SO’s is when it gets weird. Also, how did LW hide these fabulous gifts and prizes from this guy from her boyfriend? Then you move from lying by omission to just outright lying… If you’re going to have this sort of deal, at some point the boyfriend will have to know and be on board. A better system would be to either communicate your relationship needs with your current boyfriend or find a boyfriend who is more willing to “spoil” and “treat” you to the things that you like and make you feel loved.

    1. TheRascal says:

      I so agree with this comment, MsMisery. The lying is the problem.

  16. Agree with everyone else that the lying is the problem. If you are in a situation where you have to lie to your SO, either the situation or the SO needs to change.

    Also, LW, I think you are long overdue for a good, hard look at your finances, and a discussion with your boyfriend about your future together (financial and otherwise). You say he’s in a position to help you out financially, and doesn’t. Certainly he has no obligation to do so, and you should not presume that he should. However, if you are talking about getting married, you should be talking about your values, including how you handle money. Do your long-term financial goals line up? How will you pay your shared bills? If you have kids, will one of you stay home or work part-time? This is a conversation that goes beyond “I want you to take me to dinner more often” (although that is also something you need to communicate).

    Are you planning to support your mother and sister long-term? You REALLY need to re-think that plan, especially if it is driving your decision to imperil your relationship with the guy you think you’re going to marry. You said it yourself – you are selling the time you could be spending with your bf to a creepy married dude who is hoping to get in your pants. If I knew my daughter was working three jobs and being a “sugar baby” just so she could EAT, I can’t even imagine the abject awfulness that I would feel knowing that I was part of the problem. As someone said above, there are ways to help support your family without starving or resorting to shady behavior.

  17. Sue Jones says:

    Hot Chick Problems…

  18. LW–everyone has pretty well covered the lying issue and the problems with the nature of this “suger daddy” relationship.
    So, just to focus on your question–is this cheating? I think it is, on both sides. It sounds to me like a form of emotional cheating. An emotional affair ) is one based not on physical intimacy, but on emotional intimacy. It is characterized by: an inappropriate amount of emotional intimacy, deception and secrecy, increased fighting with your primary partner, sexual and emotional chemistry, denial.
    Sound familar?
    The emotional intimacy you have with this man is affecting your relationship with your boyfriend, and (even though you think you are helping him repair his marriage) it is affecting his relationship with his wife since he is using you as his primary confidant (creating emotional distance from her).
    If your primary concern is whether you are cheating or not–you are. And so is he. If you don’t want to be a cheater (or be party to helping this man cheat on his wife), put a stop to it.

    1. RedroverRedrover says:

      And LW, if you’re just going to come on here and keep insisting that it’s not cheating, why did you even ask the question? Clearly a lot of us think it is, and obviously your boyfriend wouldn’t like it either or you wouldn’t have told him. So what’s the point of asking? You already decided to just keep lying to him about it. So go ahead and do that. You’re not going to convince everyone on here that it’s A-OK when it’s not.

      1. RedroverRedrover says:

        Correction – you *would have* told your boyfriend, not *wouldn’t have*.

  19. Avatar photo bittergaymark says:

    Sure, it’s not cheating. Hey, you’re only misleading some sap with money. And you’ve got an equally classy knocked up sister to worry about. I say, GO FOR IT. But be forewarned — not everybody out there likes a whore with no followthrough.


  20. I know a ton of beautiful smart intelligent women whio would cherish an honest man. You know what your doing. It is true what goes around comes around. I say turn him out let him find a good beautiful honest hard working woman.

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