“I Cheated on My Sugar Daddy With his Close Friend”

I am a 24-year-old girl who started having an affair with her boss a little over a year ago. It was just ok in the beginning. He was a sugar daddy, per se, and I expected a lot from him, and my expectations were not met. Or they were met too late. It put a strain on me. For example, I had asked him for my rent in January of this year — rent that was due in December — but he didn’t give me even half of it until May. Meanwhile, since I worked with him, I was quite aware of his other girlfriends. He’d bring them to the office whenever he liked, which was disrespectful to me. I knew he took these girls shopping, took them on vacations, and even bought them cars. But when I asked for something, I wouldn’t get it until six months later. I really was not satisfied.

In January of this year, a friend of my boss’s who comes to the office regularly started to ask me out. My boss and I were on and off. His friend told me he liked me, and he wooed me and all that. I asked him for the rent. I was about to lose my place. He gave me the rent. He was trying to get into my pants, sure enough. But it felt really easy with him. I didn’t see him with other women and he was very responsive. So, I began a relationship with him. It was good. Until May.

Then, he stopped calling me. And then by June, my boss stopped calling too. They are very close friends. I figured they found out about my stupid game. So by July, I couldn’t take them ignoring me anymore. The friend would come around and pass my desk like I didn’t exist. My boss would do the same thing. So I quit my job. For my happiness. But every day ever since then I have been thinking about the terrible thing I did. Especially to the friend. I have been thinking of a way to make it work with either of them.

So, which do you think I should do:

1. Apologize to them separately (and if so, what is the best way to go about it?).
2. Apologize to my ex-boss because he is the one I cheated on.
3. Just let it go and move on with my life.

— Feeling Like a Bad Woman

Here’s exactly what I think you should do:

1. Let it go and get on with your life.

2. Find a new job, if you haven’t already, that pays enough to cover your rent and/or get a roommate so you no longer have to ask random men to pay your rent for you.

3. Is your boss married? If he is, instead of thinking about how you ruined things with either of these two men, think about the woman your ex-boss is married to and how you contributed to a pattern of chronic cheating in her marriage.

4. Think about how, one day, you won’t be 24 anymore. One day you might be married. Maybe you’ll even have a kid or two or three. Imagine how you’d feel if the man you’re married to — the father of your children — was sleeping with multiple other women and spending money he could be contributing to your family and household and YOU on these “sugar babies.”

5. Stop thinking about men in terms of what they can give you or get for you. Start thinking about what you can get for yourself.

6. Stop thinking about your sexuality as a commodity (unless you really want to become a professional escort or hooker). It is so much more than that. It’s an expression of YOU — of your passions and your ideas and the way you look at the world. It’s an expression of the things you’ve learned, and the places you’ve been, and loss you’ve overcome, and the joy that has filled your heart again and again and left you breathless in its intensity. It is so much more than your June rent.

7. Do something kind for someone else. Get out of your own head and stop thinking about you, you, you, and do something that will make a difference — even a small difference — in someone else’s world. You will be amazed how a simple act of kindness has the power to change the way you think about yourself and your place in the world. You will be amazed by how thinking of someone else limits the breadth of your own problems while also empowering you to tackle them.


Follow along on Facebook, Twitter, and Instagram.

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


  1. OK I could only read the 1st lines. “a sugar daddy, per se” WHY THE HECK USE PER SE???? Sorry, it´s one of my pet peeves.

    1. Now I´ve finished the letter and Wendy´s (awesome) advice. LW; please learn to live within your means. And no man (especially not one for whom you´re just another one of the girls he´s sleeping with) owes you a damn thing.
      Take Wendy´s 4th point and further it, if you have a daghter one day, would you lke it if she slept with any guy just to make rent???

      And finally, you can´t make it “work” with either of those guys. It´s quite obvious neither was intested in anything long term or serious with you.

    2. Avatar photo suzyinthesky says:

      I KNOW!!! I had to look up the definition.
      by, of, for, or in itself; intrinsically:

      1. Yeah. It´s somehow become the new fashionable term to butcher. At least LW spelled it right, I suppose.

      2. Avatar photo Dear Wendy says:

        No, she just had an editor.

      3. I suspected that! But I thought I´d give her the benefit of the doubt in one thing haha. Silly me.

    3. I just can´t leave this letter alone. LW ,it´s not cheating if the guy is also sleeping with lots of women. And if you want better gifts, maybe learn some new tricks?

  2. Beautiful, thoughtful advice by Wendy. This letter just made me want to bang unintelligibly on my keyboard and that is why this site is “Dear Wendy” and not “Dear Jenny”.

    Also, anytime your boss wants to sleep with you it’s time to find a new job because that is just bad news. If you’re financially strapped enough that you’re almost getting evicted because you can’t pay rent, then don’t jeopardize your income source by sleeping with your boss.

    1. IKR? I had to bite my tongue (fingers?) soooo much while writing.

    2. Avatar photo suzyinthesky says:

      Yeah I had to sit on my hands. Also, everything about this letter is just so, so wrong, my brain just exploded a little.

  3. Skyblossom says:

    No need to apologize. You used them for money and they used you for sex. You’ll get much further in life if you don’t have to sell your body to pay your bills. Consider your options for making a bigger income or for deceasing your bills or both. Have you gone to school? Can you take some classes that would lead to a higher income. Can you find a cheaper apartment or a roommate?

  4. So I’m trying to ignore the whole sugar daddy/ dating your boss business and just look at the basics of this situation. As far as I can see, this was all between consenting adults. You didn’t cheat on your boss and I’m not seeing how you wronged the other guy either. I mean, workplace affairs are a bad idea, but they participated in that too, and gave you their money voluntarily. So I’d say there’s no need for you to apologize. Be glad you’re not working there anymore and focus on getting a new job. If you ever get a sugar daddy again, do it out of the workplace. But I would advise earning your own money.

    1. “If you ever get a sugar daddy again, do it out of the workplace.”

      Yes, this. The only thing your boss should be paying you for is doing your actual job.

      Aside: I hope this guy owns his own company. Can you imagine if you found out one of your employees was paying his subordinates for sex? Lawd.

    2. Wendy, I didn’t see that the boss was married in the letter, did you edit that out?

      1. Avatar photo Dear Wendy says:

        You know what, I didn’t! Obviously, i read the letter several times and somehow had it in my head the guy was married, but you’re right — there’s no mention of a marriage or a wife. My bad. I’m going to go edit my response now. Thanks for pointing this out!

      2. Maybe it was the use of the word “affair” that pointed you toward thinking the boss was married? I’m not a native speaker and I wasn’t entirely sure about whether people would even call something an “affair” if there wasn’t some sort of cheating involved. (In German you could definitely speak of an “affair” even if there was no cheating).

      3. Avatar photo Dear Wendy says:

        It was definitely the word “affair.” In American English, affair usually connotates something inappropriate — like extramarital intimacy — but in this circumstance, the word affair couple simply point to their boss-subordinate relationship.

  5. Skyblossom says:

    Your boss thought it was fine for himself to cheat on his wife, he considered it fine to have sex with his own employee and then he considered it wrong for one of his sugar babies to have sex with his friend. His boundaries are all out of whack. There are so many levels of wrong in this situation. It sounds like the only relationship he protects is his business relationship. You should run from this situation and never look back.

  6. Avatar photo Raccoon eyes says:

    Wendy, amazing response. I, like the dork I am, try and anticipate your advice, and usually I’m not too far off…but reading this, all that came to me is, “This is a joke, right???”
    Also, how does one even request (demand?) rent money in this day and age? Am I just not enlightened enough?
    Blah, whatever. LW, please live within your means, and if you truly want a relationship with a man, you need to not rely on him like a “sugar baby” or whatever.

  7. This letter seems fake to me. How many friends drop by your workplace on the regular? I’m assuming the “friend” would have a job himself and may be occupied so as not to allow him to wander the halls of another workplace.

    Also, ever thought of the fact that your “sugar daddies” may not have been interested in you at all but since you were ready and willing they thought they’d have a go? I mean if they’re taking other girls out they clearly must prefer them to you. Time to learn new tricks or plastic surgery maybe otherwise I don’t see how you can “get them back”.

    I don’t know this letter screams fake. But if it is real you may have an std. As well as a host of other problems.

    1. I think it probably happens more than you think. Assume maybe that this is a small to medium business and that the friend also works in the same industry. Or perhaps the friend works a job with flexible hours and visits his friend, who in this case is the boss and probably has much more flexibility in his hours.

      1. I just can’t imagine someone with actual power like a lawyer, doctor, accountant, banker or successful businessman being stupid enough to bring his girlfriends in for people in the office to laugh at. But maybe I’ve never known trashy low lifes. Maybe they are like the only two people working there.

      2. I think it actually happens more than you think and people who you would never expect are the ones doing it. Even powerful people make shitty decisions.

      3. I don’t know I just get the vibe that they work at some small crappy place and his other girlfriends have acrylic nails (not gel even) and are orange and are named named Tiffani or kandi or staci or the alternative double e ending.

        Ahhh this letter just infuriates me please let it be fake.

      4. lets_be_honest says:


    2. My ex boss’ married friend used to drop by and flirt with me (for the record, besides being married he was not my type and too old)
      He was also a business associate, so would only drop by when casually discussing a contract. Lots of people dropped by in that casual office, the kind of people who don’t have to clock in and worked nearby I guess
      I have no problem believing this letter

    3. “Friend who comes by the office regularly.”
      I guess we don’t know if this means “office building” or “manager’s office.” I for some reason read it as a friend of the boss who worked in the same building but not the same department? So he’d drop into their area every so often? I guess it would be weird if it were a non-employee just popping in and out. My managers never have non-work visitors that often.

  8. You mention that you had an affair. Are both of these people married? What would you envision your relationships with these men looking like if it ‘worked out’? Do you think they are going to leave their partners for you? What do you want from them or from a future relationship? Are you just looking for someone to fund your lifestyle of choice or do you want a life partner? And after thinking about what you want read Wendy’s advice about 10 more times.

  9. Bittergaymark says:

    I am aghast that her boss would ever even think of disrespecting her! Usually, nothing commands respect like a bargain basement — pay me when you feel like it — whore.

    1. Seriously, you always get the money upfront. That’s like Hooking 101.

      1. Avatar photo Addie Pray says:

        Also you don’t kiss on the mouth because that, but not the other stuff, is too intimate. (Things I learned from Pretty Women. Dumbest movie ever. There, I said it!)

      2. Avatar photo Addie Pray says:

        *Pretty Woman, whoops, who cares though

      3. Re-reading (again) it seems she did with the 2nd guy at least: “In January of this year, a friend of my boss’s who comes to the office regularly started to ask me out. My boss and I were on and off. His friend told me he liked me, and he wooed me and all that. I asked him for the rent. I was about to lose my place. He gave me the rent. He was trying to get into my pants, sure enough.”

    2. A-men. You hit it right on the head.

    3. “Bargain basement” makes her sound so cheap. Surely there’s some more honorific economic term we could use, like “laissez faire.” I mean, it’s French, so it sounds sexy….. But, yes, always close the deal before you deliver the goods. The best part was how she gave it away for free and then claimed to have been disrespected. LW, kindly pull your head out of your ass and take care of yourself. Even if your plan is to be a heartless gold-digging rent-girl, you still need to take better care of yourself and make a plan that has a chance of succeeding. Use your body for what you want, that’s your business, but you are allowed to use your brain too.

  10. I can’t decide if I want to be snarky or…just slam my head into my desk. Repeatedly.
    I seriously can’t wrap my head around the idea of knowing a guy wanted sex and then ASKING HIM FOR MY RENT.

    1. I don’t even know how that would happen. I would feel strange even asking my parents for rent. But some dude who wants to sleep with me? Hey, let’s light some candles. Want to buy some champagne for us to pop and oh, by the way, can you also pay my rent even though we just met? K thanks.

      1. Well, at least the champagne and candles classes the whole interlude.

      2. *classes up.
        Good lord.

      3. It was the only way I could even think that it might even possibly come up. Then again I have not spent much time contemplating existence as a “sugar baby” (is that what you call it?) so maybe therein lies my problem. Good thing I’m almost done with work for the day…

  11. In the future when you want to make rent, sleep with your landlord instead of your boss or his friend.

    (Hopefully it’s obvious that I’m being sarcastic. If not – find a better job/get a roommate/move somewhere cheaper.)

  12. Wait… I can just ask random dudes to pay for stuff for me? Do I have to sleep with them or can I just ask nice?

    1. Bat your eyes and twirl your hair. It totally works.

      1. Smile too. That helps.

      2. Especially if you’re in your early 20s.

  13. LW, I think you’re confusing a relationship with a business agreement. These men paid you for sex. And then they got tired of paying you for sex. You didn’t ‘cheat’, unless you had an exclusive arrangement with your boss. Which you apparently did not, since he brought other women around who seemed to have the same deal you did.

    If it is a romantic relationship that you want, stop asking men for money and pay your own rent.

    If you want a guy to pay your bills and buy you stuff, consider becoming an escort. Some escorts have regular customers; the arrangement wouldn’t be very different from what you had with your boss.

    1. Exactly. We’ve all been so misled by “Pretty Woman.” BUT MY SUGAR DADDY HURT MY FEELINGS I DON’T THINK HE LOVES MEEE. No, prolly not.

    2. You’re right–she didn’t cheat, it was an arrangement. However, maybe the two friends also didn’t want to be “wiener cousins.”

  14. Crazy_Pug_Lady says:

    Please listen to Wendy. Firstly, Go get tested for STD’s!!! You were sleeping with men that had multiple partners, did you use protection?

    like Wendy said, You need to really think about what you’ve done here, while it may have been fun and easy for you to do this while your 24 what about when your 30, 35 or even 40? Also at some point sugar daddies are going to stop knocking on your door as you get older.

    1. Avatar photo Raccoon eyes says:

      I love your name, Crazy_Pug_Lady! Awesome.

  15. You had a contract…Sex for money. Your contract was terminated. No need to apologize. If other girls were getting vacations and you couldn’t get your rent paid then maybe this isn’t the line of work for you. Is this truly how you want to live your life? This is what you wanted for yourself when you were a little girl? What is the end game? Just cycling through men until they tire of you? Taking whatever coin they throw your way? If you want to be a sex worker move to where it is legal and at least get paid so you know you can make your own rent. Pretending these arrangements are relationships and not business transactions fools no one but yourself.

    1. If the other girls were getting vacations and the LW wasn’t, obviously they were better at it than she was.

      1. Not gonna lie – I thought the exact same thing

  16. This makes my head hurt. LW, you need to learn how to fend for yourself. Pay your own rent, pay your own bills. If you can’t afford to do that, live with your parents for a bit to save up or find a roommate or two. And LIVE WITHIN YOUR MEANS. Plenty of people — just like you — who are in their 20’s make it work. They cut down on their spending if they can’t make their rent payment. They find ways to earn more money in order to make ends meet. Honestly if you don’t learn to do that now you will regret it.
    Move on with your life, if you’re still at that job quit and find a different job, and I suggest staying single for a while — as in, at least 6 months. ONLY rely on yourself. Pay your rent and other bills yourself. Go out and meet new friends. Find a new hobby whether that is a new exercise or reading a new book or whatever. I think you will find being able to make it on your own very freeing and it will give you a ton of self confidence, which is something I think you are lacking right now. It is so awesome to say that you and only you are supporting yourself.

  17. Ugh! What EVERYBODY else already said!

  18. Avatar photo Addie Pray says:

    Do women like this, and men who go for women like this, REALLY exist? I mean, really?

  19. TheRascal says:

    Wendy has far more compassion than I do.
    How do people this selfish and self-centered exist? I’m baffled.

    1. Avatar photo Addie Pray says:

      I think they only exist in movies. And on DW.

  20. Avatar photo muchachaenlaventana says:

    Not to be harsh, but you were one of many young playthings for these dudes, I think you are flattering yourself to think your actions with either of them had or could have any impact on their relationship with one another. In relationships like this, it is about sex and nothing more. They probably just weren’t interested in you in that way any longer and so stopped calling and taking you out.
    So don’t apologize and stop relying on anyone else for money to pay your rent. Take care of yourself. Be an adult, an independent person who can make it in the world. If you trade on your looks for too long it will end up really coming back to haunt you. Beauty fades, but intelligence, ingenuity, kindness, skills do not. Start building some of these and leave this whole mess behind you.

  21. This letter makes me so angry. You sleep with your boss, possibly contributing to a cheating situation, ask him for money, sleep with another guy, ask him for money, and you feel you can command respect? Geez. Respect yourself first, pay your own damn rent, don’t sleep with your boss and then maybe you can ask for respect from others.

  22. For some reason I feel like this LW didn’t even have a sugar daddy/baby arrangement with this guy, per se.(<–haa) . Like… I think she was just sleeping with her boss, & then fantasized that she could get all this $$$ from him? Basically–in her MIND, if she's sleeping with the boss, then DUH, she could ask him to pay for shit. So she starts asking for rent money, & he's like… "umm, this is kinda weird, but okay?" & since he doesn't actually believe himself to be a sugar daddy, he takes 6 months (how… dare he…??) to actually bestow rent money upon her.
    THEN she starts sleeping with his friend, & they probably compared notes… like "Poor girl, down on her luck…she needed rent money." / "Wait, she asked you too??" And then both men dump her. (That's my theory, anyway)

    1. I ike your theory! And the fact you used per se right hahaa

    2. That’s exactly what I was thinking! I’ve resisted the urge to pile on her thus far, but there is something very very wrong with her perception of reality to say the least.

    3. Skyblossom says:

      I think the boss wasn’t seeing this as a sex for money type of situation. He probably has a vision of himself as an sexually irresistible guy or a great lover who is also financially generous with his lovers. Having sex and then being asked to pay the LWs rent probably doesn’t fit his fantasy of himself. He probably expected the LW to pay her rent from her paycheck like everyone else does and if she was his lover at some point, that he determined, he would give her an extravagant gift. She probably ruined the entire relationship by asking for money.

      When you are a sugar baby you have to understand the fantasy of the sugar daddy and go with it to get ahead.

  23. Avatar photo Crochet.Ninja says:

    how about pay your own damn rent? ffs.

    1. Oh, come on now. That’s just silly talk!

  24. findingtheearth says:

    I just can’t even handle this. LW, you are 24! Get a real job. Get a real life. I especially love Wendy’s advice about giving to others (and that does not mean oral sex 😉 ) When I am super mad, upset, jealous, etc., I have found this to hold true: the minute I think of others and give compliments, give help, donate my time, whatever, all my petty little thoughts stop. You have potential to be a great human being that does not rely on sex to pay the bills.

  25. “I don’t need feminism because I use my sexuality to control men and take their money, except they don’t pay, so uhhhh…..”

  26. So, this is what I can’t get over…. she needed rent money in January but the boss didn’t pay until May. Did the other dude pay in January? What about February, March and April? Who paid rent those months?

    1. The rest I can’t even address because, come the eff on….

    2. Skyblossom says:

      I’m wondering how she paid rent before she started having sex with the boss.

    3. I’m thinking Dude #2 paid her rent from January through May due to “In January of this year, my boss’s friend…. I asked him for the rent.” And then also, “So, I began a relationship with him. It was good. Until May.”

  27. Laura Hope says:

    Ultimately, in order to be happy, I think you have to like yourself. That comes more from having integrity than from having a nice apt. or power over men.

  28. lets_be_honest says:

    Meh, you are allowed to be taken care of by a sugar daddy if you wish. Nothing to apologize for there! The thing you should learn though is that its best to depend on yourself to pay rent, etc. since sugar daddy money isn’t a guarantee.

    1. lets_be_honest says:

      Also, seriously with all the STD and shaming stuff? You guys realize you can get STDs without having a sugar daddy, right?

      1. Well if she’s having an ‘affair’ affair and not calling her relationship an affair, of course people are going to call her out for that. Also sleeping with and accepting money from your boss is a dangerous path to go down, which people are also calling her out for. And of course you can get STDs without a sugar daddy, but she seems so immature in her writing and actions that it can’t hurt to remind her.

      2. And don´t sex workers make extra money for no protection?

      3. Avatar photo possumgirl says:

        Yeah, but you don’t *have* to go bareback. There’s just as many clients who don’t want to risk their own health.

      4. Avatar photo peppers87 says:

        Totally agree. I think some of the comments are being a WEE bit judgmental about the sugar baby thing, even though I agree that being strapped for rent money month after month isn’t ideal. LW, mixing the job + sugar daddy situation is probably a recipe for drama at the least, but you already survived it once with just awkwardness, so that’s pretty good. I would try finding a male cougar? outside of the office and simultaneously look for a job that can get your basic needs covered and “use” (consenting) guys (with which you have an excplicit agreement) for the fun stuff until you’re ready for a serious relationship.

    2. The thing is that she basically has no self worth. She’s literally depending on them to pay her basic needs!! That’s not ok. If you want a sugar daddy, whatever, but you (general you) need to support yourself. You need to pay your own bills. She has a LOT of growing up to do. In this letter she is whining because her sugar daddy wouldn’t pay her rent when it was due. That’s what bothered me most. She can’t even rely on herself.

      1. lets_be_honest says:

        I know tons of people who depend on other people for money – parents, husbands, boyfriends, girlfriends, wives, etc. Doesn’t mean they have no self-worth.

    3. It also helps if the guy is aware that it’s a sex-for-money kind of arrangement. I’m with Fabelle on her ‘he didn’t know it was a sugar daddy thing’ theory. If both parties go into the arrangement agreeing to it (and there isn’t a power differential, i.e. boss-employee), then by all means go for it.

      1. lets_be_honest says:

        That’s definitely a fair point about Fab’s theory. I just really don’t get all the hate on here.

      2. Avatar photo muchachaenlaventana says:

        yeah it does seem really negative. I think its not ideal to count on someone else for money or anything consistently, and having a relationship with a boss is always a bad idea, so probably avoid that in the future. I just think having a way to pay for things and being okay without the sugar daddy are skills she could really learn–then if she finds out she just likes being a sugar baby or whatever, go for it but it seems really precarious to be relying on a guy for rent –especially when, in this case, he didn’t even come through with it.

    4. Avatar photo possumgirl says:

      Can’t agree more! At least she’s honest about what she did. I do not understand why slut shaming for casual sex is a bad thing, but slut shaming because re: sex for cash is somehow acceptable. Isn’t empowerment all about using our bodies how we choose?

  29. Brian Fairbanks says:

    “It was just ok in the beginning. He was a sugar daddy, per se, and I expected a lot from him, and my expectations were not met.”

    I wish here all the worst.

  30. Brian Fairbanks says:

    ” It was just ok in the beginning. He was a sugar daddy, per se, and I expected a lot from him, and my expectations were not met.”

    I wish her all the worst.

    1. Avatar photo Addie Pray says:

      hi hi hi hi hi hi hi hi hi

      1. Avatar photo Addie Pray says:

        i mean, yo sup. i’m so chill.

  31. You did not cheat on your sugar daddy. You were a hooker, you freelanced, and then were let go. Advice –
    – Contact an escort agency and apply to work for them. They can provide you with a steady stream of clients.
    – Get paid up front.
    – Get better at your job. Obviously, you need to work better if you were let go by two clients simultaneously.

  32. Avatar photo peppers87 says:

    I think like most letters this boils down to a communication issue. You expected a classic sugar daddy/baby relationship but like some posters are saying above (Fabelle / Skyblossom), he probably didn’t see it that exact way and just wanted to be generous and have a fling with his hot young employee. If you’re looking for a sugar daddy, that’s fine, but make sure that’s what the guy is looking for too! I think the second guy knew more what he was getting into, but maybe just didn’t like that you were also involved with his friend?
    Don’t apologize. In the future, look out for yourself a little more and make sure you’re getting the type of relationship you seek. I think that’s pretty general advice, but if you spend the time making sure you know what relationship you want (Sugar daddy/baby, casual fling, serious boyfriend) and are explicit with your needs, I think you may in fact get it. Also, haters gunna hate re: being a sugar baby, but you are only 24 once! If that’s what you want, get it gurl.

    1. Yeah except for if the person is married or in a relationship, really ask yourself if that’s what you want out of a relationship. Does she really want that for herself? Maybe she doesn’t care because obviously the men don’t care. But, yeah that’s my main problem here is her use of affair. Being a sugar baby and knowing what you’re going in to and doing it with a consenting adult who isn’t attached, go for it. But, if it was me and I was part of the cheating partners cheating, I would feel pretty crappy. And I think most people would judge you for that (while judging the cheating partner too).

      1. Avatar photo peppers87 says:

        Well yeah, I guess that’s a question to answer too, down the line, but she mentions nothing of wives in her letter, so why/how can you assume these men are married? Can’t she look for single sugar daddies if she is opposed to cheating? What if she’s not opposed to being “the other woman”? What if the men are in open relationships? I think there are many sugar daddies in the sea and she hasn’t really even begun to look. She should be on her guard, yes, and aware of her own feelings on being a participant in cheating, yes, but the fact that some men cheat on their wives doesn’t disqualify her from finding a satisfying relationship with a sugar daddy.

      2. I guess I was responding to your haters gonna hate comment. She used the word affair which to me meant the person was commited and not in an open relationship. Is that what she really wants? Of course there are plenty of single men out there. And I’m sorry but if you enjoy or want to be the other woman and it’s not an open relationship people are going to judge you and I think that’s just something you have to deal with.

      3. lets_be_honest says:

        Is it really on her, a sex worker of some sort, to research whether her sugar daddies are married though?

      4. No, but I’m assuming she knew her boss was married (if he is, still confused if that’s the case).

  33. Avatar photo possumgirl says:

    I have zero hate for what you did. I fundamentally do not understand how sex for money/support is a bad thing. It’s your body, absolutely do not feel guilty for that. We are not Puritans.

    -That said-don’t consider working as an escort/sugar baby unless you can keep your personal feelings under control. That is a requirement of the job (like passing a typing test is for a secretary)
    -There are websites catering to “sugar babies”. Check it out- the job is more contractual that way and terms are clear.
    -If you do decide to look for a sugar daddy, do not plan on him paying your bills. Plan on those funds to pay for vacations, new shoes and “extras”. Take 20% and put it in your savings.

    Best of luck. This can be thrilling, enjoyable and rewarding, but in this job, you are an independent businesswoman. Act like one.

    1. I have zero respect for women who use men for money when they should be fully capable of earning their own keep. If that’s Puritanical, then so be it. But there’s difference here between what this LW is doing and being a legitimate sex worker (whom I have no problem with). A legitimate sex worker has no illusions that her business relationship with her clients is anything else. This LW seems to think that because she’s 24 and cute, she shouldn’t have to work for anything. And, if this boss is married, she may be contributing to the breakup of another woman’s marriage, which is absolutely not cool. She has all the hallmarks of a gold-digger in the making. If that’s her life ambition, fine, but she has no cause for demanding respect, at least not from me.

      1. Bingo. This exactly.

      2. Avatar photo possumgirl says:

        I’m almost 100% positive that this was a mutually parasitic relationship between LW and the bossman. We also don’t know what his promises were or his marital status, so her expectations of him might not be all in her head.

        Being 24, cute and greedy is pretty much the description of a sugar baby. I don’t believe that very many men enter into a “sugar daddy” arrangement without knowing exactly the type of person they are getting involved with. I’m saying that if that’s what she wants to do, then she needs to be more realistic about her behavior and expectations.

  34. Yikes. Ok, I am not even opposed to a woman having a sugar daddy type thing, as long as BOTH PARTIES KNOW THE DEAL, but it seemed like that was not the case here. If this is going to be a regular part of how you pay the rent in the future, then (A) always safe sex, (B) never $#it where you eat (ie, don’t DO the boss or a colleague), and (C) at least earn enough in savings at a legit job so you can pay your bills if “clients” fall through. There are actual websites where you can meet sugar daddies, if this is your thing.

    1. Exactly. I don´t know if anyone is against the concept of sugar daddies (even though the term is just gross) but think LW just seem so obnoxious, and that´s what brought out the snark.

  35. Sue Jones says:

    Well sheeeeit!!!! When I was 24 I worked 2 jobs and then started medical school where I also worked my butt off! If I only knew then that all I had to do was have sex with rich older men and have them pay for my stuff, I might have saved myself a lot of trouble becoming a doctor and all….

  36. Only 1 sentence: utterly amazed at Wendy’s ability to give such a rational response to such a letter.

    Very few could do the same. This letter actually made me lightly sad of state of the world 🙁

  37. Ugh. I’m just hoping this letter is a fake. Please tell me no one is this lazy or stupid. Please?

  38. I’m dying to know what kind of field/work happens at this office.

  39. Avatar photo Dear Wendy says:

    From the LW:

    Thank you very much for posting my letter and thank you for your advice, I am gonna go with that. I read some comments on the post and just want to say somethings.

    I am african. So maybe our (sugar daddy) relationship cliches are quite different from the western world* permit me to put it this way. My boss is married. His friend is also married.

    I did not just sleep with my boss and then ask for rent. He wooed me. Asked me out. Told me he wanted a relationship with me. We both knew what we wanted and went for it. So I asked for some financial assistance once in while. Its is only normal. Where I am from. You don’t date a married man because you are lonely and horny. You need to like the person for sure but there is an understanding between you two. So asking for rent isn’t bogus as the comments made it seem. We had a relationship so I could ask. Here, you don’t take a girl out and split the bill at the end of the night. It is really different here. Maybe I should have been more precise in my first letter.

    Rent is paid on a yearly basis not monthly as some comments presumed, and I protected myself. It was a small solo firm. Just five workers. He comes there to his little business and cordial meetings. I hope you get the scenario.

    Well, there is no way to go around it. Me mentioning rent was just as example of how relaxed he was to the relationship. It wasn’t the beginning and the end of the relationship.

    My case is just one of cheating on my sugar daddy with his friend. Nothing more, a relationship like that isn’t called for, if there isn’t any form of expectation from both parties (I say this humbly) not trying to be brash. Thank you for understanding. My Boss called me two days ago just to check on me. That is not the case. I am letting go. One of these days if I bump into any one of them and feel the need to come clean, I might.

    Your work has been very helpful to me, you can do an update on the post. I really need the opinion of others.

    1. Here there´s a saying “don´t try to clear things up, you´re making them darker”. And that´s all I could think of while reaing this update.

      1. Sue Jones says:

        Still, if the bossman has other girls and you have other guys, IMHO it is not “cheating”, you are not “property”, you are in an “open relationship”. At least that is the Western take on things. Sadly women in Africa seem to be more oppressed than most of us realize if they are considered “property” and that they are “cheating” on a philandering boss who not only is married but has other girlfriends as well.

      2. Yeah def. not cheating(on her part), just a horrible situaion all around.

Leave a Reply

Your email address will not be published. Required fields are marked *