“Is My Friend an Unwitting Sugar Mama?”


My closest friend has a history of hooking up with really rotten men who initially seem charming, into her and into her very quickly. She finally got rid of the last one a year or so ago (he was very bad news – stole from her, used hard drugs, had multiple women he was crashing with) and has been doing really well.

Two months ago, at an event my boyfriend and I invited her to, she hooked up with a man 25 years her junior, and they’ve been inseparable ever since. As in: he spent the night at her place the night they hooked up and simply never went back to his (sketchy) home. It very quickly became “So & So and I” and “I’ll see what So & So” thinks when talking about issues going on in her own apartment. I think how quickly he swooped in on her (cooking, flowers, lots of big gestures but then a total drop-off in sex after the first few weeks) is a big red flag, and he “lost” his bank card a month ago and can’t seem to get a replacement or money, so she’s paying for everything. He drinks a lot. When I’m around, he pretty much fixates on me to the exclusion of my friends, while declaring that he “loves” me and that I’m his favorite of my friend’s girlfriends. I feel as if I’m being manipulated. He was supposed to leave for a job at the beginning of this month, and then the date was pushed out a few weeks, and today I found out that now he’s not leaving for another month. (My boyfriend predicted he’d do that.)

My friend IS suspicious of the money thing, but she’s very happy and says he treats her really well, gives her lots of physical affection, is really nice to her and takes her on adventures that she wouldn’t otherwise go on. I’ve seen those things in their relationship, but I don’t trust him and don’t want to hang out with him because his comments are so stupid and I hate fending them off. They keep asking to do things all together, but my boyfriend doesn’t want to hang out with the new guy, and in the meantime I’m really worried that my friend is being taken advantage of. I’m worried that if I say something negative about him, that she’ll tell him and he’ll find a way to get me cut out of her life. — Not Into Her New Man

So, your friend, who is with a man 25 years her junior, is very happy, is being treated well, gets lots of physical attention, and is going on adventures she wouldn’t otherwise go on? I mean, it doesn’t sound like she is being taken advantage of. It sounds like she knows exactly what she’s dealing with and she’s fine with it. It also sounds to me like you might be a little … jealous?

Regardless what your feelings are about this man, your friend sounds happy. If she’s being taken for a ride, you need to trust that she’s a grown adult (at least in her mid-40s, I’m assuming), who has been down this road before and knows the deal. Let her have her fun. So what if having the fun is costing her money. So what if this guy is “using” her? If she’s getting something out of it — fun, companionship, physical intimacy, adventures she wouldn’t otherwise get — then it sounds like a mutually beneficial arrangement. And who knows — maybe there’s genuine respect and fondness, if not true love.

If you don’t like the guy, limit your time with him. If you’re invited on double dates or whatever, make up some excuse about having plans. In group settings, avoid being alone with the boyfriend, and, if he continues to make inappropriate comments, tell him you’re uncomfortable and ask him to stop. If you’re seriously concerned that your friend — your friend who is not some inexperienced 20-something — is so malleable that she can be manipulated by this new boyfriend to stop being friends with you just because he has decided he doesn’t like you, then perhaps your friendship isn’t as strong as you thought. Or maybe you are underestimating your friend. Or maybe you’re just looking for a reason not to like this guy.

At any rate, try to do more with your friend one-on-one instead of with significant others. And if your friend isn’t available as much anymore because she’s busy enjoying the company of her young suitor, suck it up. Such is life. Friends often disappear in the early months of a new romance and then they reappear once the couple bubble pops a bit. If this is the case with her, she’ll probably have some fun stories of adventures to share with you.


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


  1. Dude. The title and accompanying photo are effing hilarious. I’ll go back and read now.

  2. I’m with Wendy, she’s a very witting one.

    1. Or “Right on the money! that’s Norma Desmond, that’s Norma Desmond, THAT’S NORMA DESMOND” for musical theater enthusiasts.

  3. Yeah, the fact that she’s suspicious, but then qualifies it with all the good things she’s getting make me less concerned. And I think this is like anything else, a person is not going to change unless THEY decide to change. You can’t just sweep all the crappy guys out of her life — she’s going to have to decide that she wants better.

  4. The LW’s friend must be, at a minimum, 45 years old. But age is not always a good barometer of maturity and good decision making. Since they’re close friends, I would speak up. Have an honest heart to heart with your friend about your concerns. If she cuts you out of her life, why would you want to be friends with her in the first place?
    Secondly, if you feel uncomfortable around this guy, you don’t have to hang out with him, period. If your friend asks you why, be honest with her, and give her examples of how he’s made you feel uncomfortable. If a guy I was dating ever made one of my friends feel uncomfortable, I would apologize profusely and try to remedy the situation. If she doesn’t – again – why would you want to be friends with her?

  5. Agree with TECH… maybe there’s a hint of ageism in that if the LW was younger the advice would be different or more concerned? being 30 or 40 or 70 doesn’t automatically make you experienced in a good way. Could still be repeating terrible patterns, be a doormat, getting taken advantage of, or a terrible judge in character. Whereas a 22 year old could be mature and wise in the ways of the world. Sadly this friend may be really insecure and while lacking in self-esteem ends up over compensating with money and the extremely quick rush to attachment and exclusivity (which is a red flag).

    That being said not much you can do. You don’t have to hang out with people who you don’t like, feel weirded out by (trust your instincts!) or just simply don’t enjoy their company. Stop with the double dates. Spend some time with your friend 1 on 1 and express concern without judgment. Best you can do.

  6. Avatar photo Regina Chapman says:

    I disagree with Wendy. Maybe the friend knows exactly what the deal is, but you don’t automatically have to be jealous to be concerned about a friend’s welfare. And doesn’t everybody have blind spots when it comes to love and dating, regardless of how old they are? I took this as one of those cases where the friend is jubilant about the situation – ‘he gives me tons of physical affection!'(but no sex, apparently?) – but the LW has the distance to see the situation for what it really is.

    Anyway, LW, I’d try to bring it up at least once. Voice your concerns in a non-judgmental way (or as non-judgmental as you can get) and kind of give her that outside perspective that she may be lacking. After that it is up to her, and if her boyfriend still bothers you, like others have said, you have no choice but to keep your distance. But if this is a genuine concern of yours, and – by your honest knowledge – not just colored by jealousy or something, then I think you owe it to your friend to alert her. Once. After all, what are close friends for if not to tell us the unpleasant truths we try to avoid in our special-love-bubble?

    1. I really like this advice. If I were you, I would do this, LW. Definitely bring it up in a non-judgemental way. Keep it light. Voice your concerns. Let you know your friend you are there for her. And then after that, it’s up to her. But at least you know you tried.

    2. Bon Vivant says:

      ” ‘he gives me tons of physical affection!’(but no sex, apparently?)”
      This struck me as odd…and led me to believe that she is being taken advantage of. Especially as it seems she’s bankrolling the fun and good times and the intimacy has “totally dropped off” early on.

      1. “Dropped off” could mean many things though. I mean if it’s dropped off from 3 times a day to 3 times a week, that’s not horrible.

      2. Bon Vivant says:

        But this is what the LW said: “… but then a total drop-off in sex after the first few weeks”

    3. I also think there’s more to this situation than Wendy does. Especially since the coupe isn’t having sex anymore, but the boyfriend is hitting on LW:

      “he leads conversations in a sexual direction and pretty much fixates on me to the exclusion of my friends, while declaring that he “loves” me and that I’m his favorite of my friend’s girlfriends”

      Did anyone else find this very disconcerting?

  7. Avatar photo lemongrass says:

    It is not your place to dictate who your friends date. You don’t have to like him, you don’t have to hang out with him but you do not get to make life choices for your adult friend of sound mind.

  8. Wow. Maybe it’s because I’m only operating on 3 hours of sleep and I’m already craving a stiff drink, but I thought this letter was full of red flags and didn’t really detect jealousy in the LW. I thought, “Ladies, now THIS is what a mooch looks like!” (Compared to the letter the other day with the screenwriter where it could kinda go either way).

    But I guess Wendy’s right anyway (as usual) because as a friend, there’s not much you can do.

  9. Something to think about, with regards to how he acts when you’re around – it could be that he knows how much you mean to your friend and is trying to gain your approval in an unfortunately sycophantic way. My best friend in the whole world is dating a guy that I could not stand when I first met him. What you describe is almost exactly how he acted towards me, and it was all because he was worried that I was going to come between him and my friend if I didn’t like him. I really do like him now, he is absolutely a wonderful partner for my friend, but I had to give him a chance. You sound like you never even gave him a chance and are looking for reasons to drive a wedge between your friend and her boyfriend. Look at how easily you brushed off “lots of physical affection, is really nice to her and takes her on adventures she wouldn’t otherwise go on.” That’s HUGE. And in most relationships there is a money imbalance. You might ask yourself if how you view this relationship is tainted by traditional gender roles, and then remind yourself that by taking this sort of view without a VERY good reason, you are selling your friend short by saying he’s interested in her for her money.

  10. The one thing that stood out to me was “he drinks a lot”. That, to me, is enough to warrant a discussion. Like Regina said above – just once, though. Don’t repeatedly nag, brig it up and (regardless of the outcome) then drop it.

    1. Avatar photo lemongrass says:

      A lot is very subjective. If the lw doesn’t drink at all then “a lot” could be a couple beers a few nights a week.

      1. You said what what I was thinking. In that “he drinks a lot” could mean anything and I wouldn’t call it a red flag. To some people, I probably drink “a lot”. I’m certainly not shady, or dependent on alcohol and I hope my character wouldn’t be judged based on what and how much I drink.

      2. Avatar photo GatorGirl says:

        I agree. I “drink a lot” to my mom (who drinks nothing), but not in comparison to our friends (or a lot of y’all on DW). It’s so subjective.

    2. I didn’t mean it as a way for anyone’s character to be judged. I meant it as a way for the LW to bring up a discussion – it seems to bother her since she brought it up. There was one guy I was seeing who my best friend thought drank a lot. I didn’t, but she brought it up (once) as a reason that she didn’t want to be around him. It made her uncomfortable. So, I tried to keep that in mind if we ever all got together.

      1. Still though, I wouldn’t go the drinking route. I mean, by that logic, any of my friends who don’t drink a lot could bring that up to me. Let’s say I’m hanging out with a group of friends and I’m drinking my normal amount, which could be considered a lot to some, and someone new to the group decides he or she doesn’t like me for whatever reason, they could then use my drinking as the catalyst?

  11. Add much as I would like to think the best of this guy and this friend, I think the fact that this is a pattern for the friend (finding guys who take advantage of her) should be taken into consideration. I’m guessing the adventures she wouldn’t otherwise go on are paid for by her. Also if the sex dropped off in the first few weeks, the physical affection is like cuddling and holding hands? That’s pretty quick to get out of the sex honeymoon stage, especially if the courting began with sex. I don’t know, this is sending up major red flags for me…

    At the same time, there still isn’t much you can do about it. If you voice your disapproval over and over, she’ll just stop listening. I would continue to hang out with just her and be available as a sounding board, like with the money concern she’s already shared with you, and hopefully she’ll come to her senses, like she did with the last guy. I had a friend who dated a guy that took advantage of her kindness that me and boyfriend didn’t like and it imploded on its own in a few months.

  12. I don’t know. I don’t think the LW is jealous as much as concerned about her friend. Fair enough. This thing could go a few ways. It could be that the LW’s friend is one of those people who falls in love with every man she dates and decides he is The One and gets taken advantage of and is inevitably hurt at the end when it turns out the only thing that particular 21 year old man wanted with a woman in her mid-40s is some no strings attached fun that she bankrolled. Or, it could be that the LW’s friend just got out of a shit relationship and is looking for a hot, young stud to provide some no strings attached fun that she is happy to bankroll for awhile. Or it could be that this is a true love match, and the LW’s friend doesn’t mind bankrolling their fun.

    There’s nothing the LW can do about it in any scenario. It’s not her place to police her friend’s love life. And, from the letter, it appears that the friend is going into this with eyes wide open. She’s been around this block previously. She knows the bank card thing is shady. She knows she’s paying for everything. Unless she’s going broke doing so, it’s not really a problem if one person always pays as long as both parties are happy with that arrangement. And, it seems like the LW’s friend is happy with the arrangement. So, the LW should leave it alone. Spend time with your friend without the BF and let this thing play out however it will while being the supportive friend you know you should be.

  13. I haven’t read every comment, so maybe someone’s mentioned this already. But if the genders in this story were reversed, I’m betting the LW would not bat an eye. The friend is a grown-ass woman who can make her own decisions, including to waste money on a boy toy. (Does anyone still say boy toy?)

  14. Bittergaymark says:

    Even IF the friend is unknowingly being used — a big if by the way — some people are not only willing to be used, but totally get off on it. And I’ve learned from experience that these people REALLY don’t take kindly to having the obvious pointed out to them.

    Wendy is TOTALLY right here.

    And I laugh at how some of you fail to see the obvious jealousy. HELLO! The entire obsessive tone of the letter just DRIPS with it.

    None of this is any of your business, LW. No matter how much you wish to make it so…

    1. If anything, I see judgment and meddlesomeness that lead to concern because how can the LW’s friend be okay living like this, she must be in trouble! But not jealousy. Agree it’s not really the LW’s business, though, no matter how much she wants it to be.

  15. Maddie Gray says:

    This LW is either jealous or just the type who likes to meddle or dramatize things or all of the above. LW, I’d relax and spend less time with your friend with the significant others around as Wendy advised. Everything sounds just fine for now. If that changes and things go south, well then be there for her if/when she needs you. It sounds like your friend has control of this for now.

  16. Bittergaymark says:

    PS — When a woman (or man) sets their sights on dating a hot piece of ass 25 years their junior… Uh, it’s pretty much a given that they will be the one paying for pretty much everything. That’s how these things ALWAYS work in the real world…

  17. Avatar photo Dear Wendy says:

    What if the tables were reversed and it was an older man with money who was hooking up with a munch younger woman? What if that woman provided physical intimacy, adventures, and made the man happy? Would people still be so concerned that the man was being used? We see/hear of those kinds of relationships all the time and if there’s any worry about one person being used or exploited, it’s usual concern for the younger woman. Why is it that the woman is always the one being exploited, regardless of whether she’s the older more experienced person or the younger, less experienced one? Is it so crazy to think that maybe this woman, who is at least 40-something and has a pattern of choosing these kinds of men, knows what she’s doing and LIKES the dynamic?

    1. I think those women are usually called gold diggers, and it’s not a compliment. I’d think a guy who supported someone like that was an idiot too.

      1. Seriously, if some 25-year-old moved in with my dad the first day she met him and then “lost” her bank card, requiring him to pay for everything, I’d be concerned. Even if he was happy to have a young piece of ass.

      2. I can see that, but I think it’s also interesting to look at it not just in the perspective of the man. We’ve gotten letters in from people before about dating an older man, and generally, people tend to think the man is exploiting the younger person, not the opposite.

    2. I think this is a valid point. When there’s an imbalance of power or money or age, we tend to view women as the victim, which isn’t always fair. My read on the letter is that these are two women who are close friends who know each other very well, and the LW is legitimately worried. If she had said how strong and confident her friend was, that would be a different story. But I get the feeling the LW’s friend is not like Samantha from Sex in the City. It seems like she has made a series of bad decisions and is pretty vulnerable.
      That being said, she’s a grown woman. She makes her own decisions.

    3. Also (sorry. thoughts keep popping into my head), I think there are two types of “sugar daddies/mamas.” The first type is like, “Har har har I just buy stuff and I get the sex with the young hottie!” (think Hugh Hefner), and the second type is more clueless and blinded by love (like Anna Nicole’s husband, maybe?)

      If you’re the first type, I’m not gonna high five you. I’ll probably think you’re gross. And if you are the second type, I’ll be concerned.

      If LW is the first type, then the friend should back off. It sounds *to me* like she’s the second type, so I understand that the friend is concerned, BUT ALSO I still think she should back off because it’s none of her business.

      Whether or not I thought the LW’s friend was being “used”, I would still be concerned because that relationship is full of red flags as far as how fast it moved.

      1. Maddie Gray says:

        I like your distinction between the two types of sugar-parents. I’d just add that for the second type, I’d too be concerned but I’d also think the sugar-parent is a complete idiot and delusional for NOT knowing, or at least speculating, that the hot young thing is with him/her for the money. But yup, I’d still be concerned. But I do think Wendy’s point is a good one – if the tables were turned, we probably wouldn’t be AS worried that the man is being taken advantage of. Which is kind of a shitty double standard.

    4. If my friend was a man with a history of getting involved with the same type of younger women who were taking advantage of him (at least in my view)? I wouldn’t beat around the bush so much as I would with a female friend and actually voice my concerns. But that’s because I don’t think that’s a healthy dynamic for anyone no matter which gender is the one with money/power.

    5. Avatar photo meadowphoenix says:

      While I think it’s a good exercise to see if there’s gender biases in play, I think it’s important that we don’t forget the context of those biases. The context of this is that men have, for a lot longer time and in greater numbers, had tacit approval for these types of relationships, and therefore in some respect, are usually aware that the relationship is a transaction, because socially that’s what people assume anyway. It’s already a possibility. Cougars on the other hand seem like recent social circumstance (even though it wasn’t completely infrequent before).

      I also feel like there are some Woody Allen undertones here, but I freely admit I’m reading into your words a bit.

      But to your point, if a guy had a history of lopsided relationships, that he would be upset about afterwards, yes, I would be worried.

  18. Bittergaymark says:

    Because, WENDY, men are EVIL!!


    I agree. It is beyond silly to infantilize a grown women. “Who cares if she ‘s older, she still might be really immature!” It’s also SEXIST. As yes, it does assume that women must ALWAYS be cast as the victim.

    NEWSFLASH! Sexy, young, hot things cost money.

    Men have KNOWN this since the dawn of time. The friend here is no idiot. She’s simply having a great time and clearly knows the cost of admission to this ride.

    1. Another funny side issue to this is the way in which we, depending on context and our biases, alternately applaud or demonize people who pay for relationships, intimacy, sex, whatever. I have the same bias, not out of antiquated morality, but more out of elevating sex to a special “sacred” status. (Which is guess is a form of antiquated morality.) I can hear myself pontificating: “I have NEVER and WOULD NEVER pay for sex! Harumph!” And I have never paid a prostitute, for example. But oddly, the only price I have ever paid for sex, love, friendship, companionship, is everything I have ever owned or ever will. because in a cynical sense, that’s what marriage is: a love relationship that has been overvalued out of the class of prostitution merely by virtue of the incredibly high price that is paid. By both! Don’t just quote me – lots of feminist writers have said this.

      1. If both parties are aware that a transaction is taking place, then I’m OK with it. Prostitution is at least honest. Unfortunately, I think some people get “used” for their money while remaining blissfully unaware. Whether or not the LW’s friend is unaware or embracing her inner cougar is up for debate.

  19. As long as your friend can afford to maintain her lifestyle with her young lover, I don’t see a reason to meddle. Now if your friend is barely scraping by and is now taking on a huge financial burden, that would be a reason for concern. However, I think this would have been mentioned in the letter if it was an issue.

    “When I’m around, he leads conversations in a sexual direction and pretty much fixates on me to the exclusion of my friends, while declaring that he “loves” me and that I’m his favorite of my friend’s girlfriends.” – he is probably joking, especially if he’s saying this in front of his girlfriend.

  20. Bittergaymark says:

    CatsMeow”s TWO theories of sugar persons are both so needlessly judgemental and — frankly — holier than thou. Not to mention rather cruel and ugly.

    Why not a third version.

    Hey, I, A, want companionship and what I lack for in youth and beauty I make up for in coin — which dovetails nicely with B who makes up for in youth and beauty what they lack in coin?

    1. Hm, I don’t think Cats meant any judgement in her description, but I do agree a 3rd type should be included.

  21. Avatar photo meadowphoenix says:

    I feel like your friend does know what’s going on, but since she’s happier than in those other relationships, doesn’t care.

    I think you are kinda mad that your friend can’t see how uncomfortable he is making you, so you’re trying to make it about other issues. If you don’t want to spend time with him, just spend time with your friend. If your friend asks why, just tell her he make you uncomfortable. Or tell him to knock it off with the sexual comments yourself. In fact, do that first.

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