“My Husband’s Friend Wants to Sleep With our Daughter When She Turns 18”


My husband, Don, and I have a wonderful relationship, but there is one issue that keeps coming up that we can’t seem to resolve. We met through a mutual friend, Jack. Jack was a friend of mine from high school and he was also my husband’s college roommate (and best friend). Jack has always been an asshole. In high school, his behavior was usually directed at other people, so I accepted it as part of his personality; plus, I was immature and thought his behavior was amusing. After college we both lived in the same city and re-connected. I became friends with his girlfriend, and she and I ended up renting an apartment together. Jack basically moved into the apartment, which was fine, but his asshole behavior was becoming an issue as he had zero respect for me or the apartment. Halfway through our lease, Jack and his girlfriend decided to move to another city, and, since my relationship with them was very unpleasant at this point, I was happy for them to leave even though it meant I needed to find another roommate.

After they left, I did not speak to Jack for several years until he got in contact with me and we met for drinks and became friendly again. At this point he was no longer with his girlfriend. This was around the time Jack set me up with my now-husband, and everything was fine for a while.

The big change in my relationship with Jack happened when he lied about being single so I would help him hook up with a friend of mine. Thinking that he was single, my friend went out on a date with him and they ended up sleeping together. A few days later, he calls me and tells me his plan worked exactly how he wanted it to: that he had, in fact, recently gotten back together with his girlfriend but told me they were still broken up so I would communicate that to my friend and she would sleep with him. On top of this, he told me that Don knew he hadn’t broken up with his girlfriend and didn’t say anything to me. He was actually boasting about this to me. After this incident, I decided that I did not want Jack in my life at all.

This created an 8-year rift with my husband as he still wanted to be friends with Jack, and I didn’t want to ever hear his name again. The times Don has hung out with Jack since the incident have not gone well. I feel like Don has the weaker personality and he picks up Jack’s characteristics, and I can see the influence Jack has on him – drinking to the point of puking everywhere, gambling, and poor decision-making, in general. Jack even tried to hook my husband up with another girl and sent him nude photos of said girl. He has tried to break us up and cause conflict in our relationship. He even said he would try to sleep with our daughter when she turned 18 (who the fuck says that about a baby?!).

For these reasons and many more, I think my husband should give up his relationship completely with Jack and should not communicate with him at all. I feel betrayed by my husband when I eventually find out he has been communicating with Jack. He says he understands my feelings, but then he continues to secretly communicate and/or get together with Jack, and I find out and we have the same argument over and over. This is basically the only thing we argue over.

So, Dear Wendy, am I being too controlling or am I justified in my desire for Jack to not be part of our life in any way, shape, or form? — Not a Jack Fan

This has been going on for eight years? Then, it’s not likely to change. Whether you understand it or not, Don gets something out of his friendship with Jack that he doesn’t get elsewhere. Maybe in his communication with Jack and, I’m assuming, the limited in-person interactions they have, he enjoys nostalgia for his college days. Maybe he feels young again for a few hours. Maybe he simply appreciates getting a peek into a completely different life. Maybe it renews his gratitude for the life he pursued — the more stable one, with a wife and kid and moral responsibilities. And maybe, for all the bad Jack has clearly exhibited, underneath it all, there are some redeeming qualities that Don still enjoys. After all, you were once Jack’s friend; you must have seen something in him that you liked. Whatever it was that once drew you to him is likely what draws Don to him, and the things that have turned you off have not been as big a turn-off for Don to cut ties with his friend. Obviously.

You say Jack has a negative influence on Don, to the point that Don drinks ’til he pukes, and gambles, and makes bad decisions. How often is this happening? Once or twice a year? If so, I’d let it go. Tell Don he’s free to hang out with his friend, but if he ever drives while drunk or gambles away a lot of money or gets himself into “trouble” (however you define that, and you should be clear with Don about what that means to you), he will have to answer to you. But if he’s out with Jack on a more frequent basis and Jack’s influence is truly affecting your life — in more than your simply being annoyed by Don’s questionable choice in friends and what you perceive as his lack of loyalty to you — then you have justification to ask, and even demand, that he stop communication with Jack or there will be consequences. And if he doesn’t — or you can’t trust that he has — the consequences of that should include marriage counseling to work through this rift, find common ground, and address the issues this friendship has created in your relationship.

Finally, if Don decides to continue his friendship with Jack in limited fashion (in-person hang-outs once or twice a year), you have every right to demand that you and your daughter never be exposed to him. Your daughter should never know Jack personally,and, if she knows about him at all, you can tell her he’s a friend of her father’s who is not a friend of yours because he doesn’t respect you or women in general. If she asks why her father would be friends with a man like that, you’ll have to tell her to have her dad explain that one.


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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. RedRoverRedRover says:

    As upsetting as it is, some men seem to have a blind spot for when other men treat women badly. It sounds like your husband has this. If it were me, it would cause me to lose a bit of respect for my husband, honestly. But, like Wendy said, maybe he’s living vicariously through him or something, and needs this release to be a stand-up guy the rest of the time. I agree that if it’s just once or twice a year, you should follow Wendy’s advice.

    1. anonymousse says:

      Yeah, I can’t even imagine my husband having a friend like this. I would have a hard time socializing with anyone who said something that disturbing and sexist about a child, let alone my own.

  2. I disagree with this one. It sounds to me like Jack is actively trying to fuck with your family. How is your husband ok with that? What does Jack have to offer that makes his awful behavior something that can be ignored.

    How would your husband feel if one of your friends was trying to hook you up with someone else? Best case scenario, Jack is button pushing with what he says about your daughter. Worse case, his lack of boundary issues will make her someone to fixate on. I don’t have a lot of hard lines, but if this were me, Jack would not only be unwelcome, I’d have a really hard time with my husband being able to justify spending time with someone that was sexually creepy as hell.

    1. Avatar photo Dear Wendy says:

      Oh, I agree Jack sounds like he’s fucking with the family. But it’s hard to forbid a grown adult to spend time and be friends with someone. Aside from threatening divorce, what recourse does the LW have? I think it’s better to “let” him continue this friends, with some boundaries, and not give jack more ammunition to use against them. The LW and Don have been married for several years and have a daughter together; is this an issue that should destroy their marriage?

      1. RedRoverRedRover says:

        This was my thought exactly. It sounds like this is a big issue in their marriage, it’s causing a lot of fights. Does she want to risk her marriage over this? Or does she want to accept it and control it as well as she can? Those are really her only choices here, because her husband’s already made it clear that he’s going to keep hanging out with Jack. As shitty as that is, that’s what she’s got to deal with.

      2. Well shoot Wendy, if you’re going to be all mature and constructive about things =)
        But yeah, the LW can’t really forbid the husband from seeing this guy, and it doesn’t seem worth breaking up a marriage over. It blows my mind that the husband can somehow rationalize it? The description of Jack really pushed my buttons! 2 more days.

      3. snoopy128 says:

        I’m with Wendy on this.

        But I would also add that if you can stay cool and not get more worked up about it, there’s space here to have a conversation with your husband about boundaries and friendships. What lines can a friend cross? When is it too much. How do you set boundaries with friends?

      4. Unwanted_Truth says:

        I’m kinda on the fence here with this one. On one hand I can see Wendy’s point, on the other Taylor did point out something that I think think i’d have a huge issue with. That is the fact that if the shoe was on the other foot, if for example my wife had a friend that was a bad influence to the point of trying to get her to cheat on me and the marriage, I think that would be just cause to demand that the friendship end or else. I think there is a thin line sometimes when it comes to telling or asking your husband/wife who they can and can’t talk to or be friends with, but I’d def be the asshole and demand that you not be friends with the person that said that they would fuck my daughter once she turns 18. NOPE sorry

    2. RedRoverRedRover says:

      @Unwanted_Truth, problem is she already told him she wants him to stop being friends with Jack, and he went ahead and did it behind her back. What else can she do? If it were the husband writing in, I’d tell him he needs to prioritize his wife’s feelings over his friendship, given how badly the friend is acting towards his family. But since he isn’t writing in, and he’s clearly decided he’s going to stay friends with Jack regardless of what she thinks, she’s left with dealing with that. Or ending the marriage, which it doesn’t sound like she’s anywhere near wanting to do.

      1. Unwanted_Truth says:

        @RRRR Yea…I have to agree. It’s a shitty situation all around frankly.

      2. Avatar photo Skyblossom says:

        It is very similar to an emotional affair with the sneaking around and lies. Don is obviously getting something out of it to the point that he is willing to risk his marriage to continue hanging out with Jack. I wonder if Don realizes he is risking his marriage.

  3. artsygirl says:

    LW – I am disturbed that your husband refuses to cut off contact with Jack after he sent him nude images of a woman and encouraged him to engage in an affair and then made comments on your infant daughter. You can ask your husband how he would feel if a friend of yours had done the same thing, my guess is he would be hurt and would want you to break off contact.

    1. anonymousse says:

      I can’t even believe this behavior. The husband is probably just as bad as Jack.

  4. If it were just a question of Jack being sketchy I’d say just note your disapproval and leave it alone. The trying to hook her husband up with other women* IMNAAHO kind of moves this into a marriage-issue rather than “I disapprove of your friends” issue. If your husband gets drunk and gambles because this guy pressures him, maybe he hooks up with some girl too.

    *It’s not clear what the “trying” from Jack entailed. If he just sent him some pictures and said “you should have sex with this woman” that’s terrible but probably not a threat to your marriage.

    ** Men and women, don’t email people naked pictures of yourself! It won’t end well.

  5. Northern Star says:

    I would guess everything Jack does is a “joke,” meant to be “funny.” That’s why Don doesn’t see his comments about your marriage or your daughter as a problem. He’s “joking,” after all!

    There probably isn’t anything you can do about Jack, and Don will do what he wants to do—but you can make it CRYSTAL clear that your husband is responsible for his behavior, and you will not tolerate any “jokes” that include cheating, gambling to excess, or illegal activity. That’s a fair line to draw.

  6. Avatar photo Skyblossom says:

    I think that often you get further and make a stronger point by asking a question rather than telling him what you want him to do. Instead of telling your husband you don’t want him to hang out with Jack anymore I think you need to ask questions.

    Why do you hang out with Jack when he is actively trying to destroy our marriage?

    When your husband says that Jack isn’t trying to destroy your marriage you ask what he thinks the urging him to cheat on you was about. How would that affect your marriage. Ask him if he would mind if you hung out with a friend who sent you nude photos of a guy and encouraged you to have sex with them. Ask him if that is fine.

    I’d go ahead and tell him that when he keeps someone like Jack in his life it makes you lose respect for him because he allows Jack to treat your marriage badly.

    I’d also ask what he thinks about Jack wanting to have sex with your daughter. As a dad how can he hang out with a guy who wants to use his daughter for sex. Tell him you don’t think that is funny and you are appalled that he would continue the friendship under those conditions. Ask why he is prioritizing the friendship with Jack over the well being of his daughter. Tell him that most men don’t talk about wanting to have sex with their friend’s daughter. I’ve personally never run across that.

    Does your husband have any other friends? Is he tolerating this because Jack is the only friend he has.

    1. “I think that often you get further and make a stronger point by asking a question rather than telling him what you want him to do.”

      I like this. I’m going to use this one.

    2. I like this approach!

  7. Yes, I think Jack is trying to be “funny.” I worked with a guy like that. He really wasn’t a bad person, just very immature (for a 50 year old), and he truly didn’t know the line between gross/obnoxious and funny.

    Speaking of lines, I think the one you draw, LW, is with your husband’s behavior. Yes, Jack is an idiot, but that doesn’t mean your husband has to act like one. As Wendy said, it’s tough to tell an adult who they can and can’t be friends with. But you certainly can object to excessive gambling that affects your family finances, and being puking-drunk on a regular basis. Those are your husband’s bad decisions, and he has to own them.

    So, instead of arguing with your husband about who he hangs out with, try focusing on his own bad choices.

    1. Avatar photo Skyblossom says:

      I’m guessing that Jack is also getting an ego boost out of inserting himself into Don’s life. Jack can feel powerful and in control when he gets Don to do stupid things. Kind of like a puppet master. Don may have the wife and kid but Jack can still pull his strings and get him to do things that harm his marriage and can even talk about having sex with Don’s daughter. He’s using Don as his personal doormat and I think that is a huge boost to his ego.

      I think the LW should point out to her husband that Jack is manipulating him, probably to boost his own ego.

      1. snoopy128 says:

        I totally agree with skyblossom’s analysis here. Jack is getting a huge ego boost out of walking all over Jack. He’s pushing boundaries and Jack isn’t pushing back.

        I find people who try to be ‘funny’ that pushes boundaries past a certain age *know* they are pushing boundaries but do it anyways because they get a kick out of seeing how far they can go.

  8. Avatar photo Skyblossom says:

    I’d go for counseling. Marital if your husband will do it and by yourself if he won’t. Even if you go by yourself you will find out how to talk to your husband and how to set boundaries.

    1. dinoceros says:

      I think it *only* has to do with her and her husband. Sounds like she’s put up with him being a jerk until the point where it started to affect her marriage (for example, her husband being encouraged to cheat) and family (her daughter being objectified and her husband not caring.

    2. Skyblossom says:

      She’s invested in this because Jack is trying to break up her marriage and because Jack has expressed an interest in having sex with her daughter. She is invested because Jack doesn’t respect boundaries and he doesn’t respect her marriage and because he doesn’t respect her husband or herself or their daughter but her husband keeps him in their life. She is invested because Jack is having a direct, negative affect on her life.

  9. dinoceros says:

    I think this goes beyond “you can’t tell a grown man who to be friends with,” though. The LW says they fight about this all the time. It has caused her husband to lie and keep secrets from her. I would seriously doubt my husband’s character if he didn’t have a problem with someone who tried to convince him to cheat and break up the marriage, and wants to sleep with our baby daughter. I suspect that the LW has been trying to convince herself that her husband is not like *that* and that’s why she’s so intent on this narrative that he is entranced by this friend. But I don’t know any men who wouldn’t be appalled by the daughter comment (except maybe Donald Trump), so the fact that he’s cool with it, to me, says a lot about him. I wonder if he’s more like the friend that she realizes, and he just uses it as a way to let himself off the hook?

    Anyway, I DO think this is a big deal for their marriage. No matter how trivial others may think a certain issue is, if it’s causing frequent fights and causing one partner to keep secrets, it will eventually implode the marriage. I don’t think the LW should avoid doing anything about it for fear of risking the marriage, because I don’t think that her bottling up her anger over this and the husband’s tendency to lie and hide things is going to be sustainable.

    Counseling, I think, would be really important.

    1. Avatar photo Skyblossom says:

      I agree. This will destroy the marriage if it isn’t dealt with.

  10. for_cutie says:

    Agreed. Someone should ask your husband what kind of man he wants to be. The type that cheats and allows jokes about his young daughter’s sexuality to be voiced, or the type that respects his vows and the women/people in his life. Maybe he has not thought of it this way before. And you could use some help articulating this to him.

    I also wonder, since your husband allows this behavior in his life, if there are not other issues in your relationship you failed to mention. It seems odd that you would have a picture perfect spouse, partner, and co-parent, who parties to the point of puking and allows this disrespectful talk of his loved ones. Something doesn’t jive here.

  11. Reading between the lines–I sense the LW trying to adopt a reasonable tone and trying to be fair and adult about this “conflict.” I see this conflict as dangerous to her infant now and in the future and dangerous to LW and her marriage. Just as she cannot forbid a grown man from doing something, this same grown man cannot be led by another grown man to drink to excess or to gamble. The husband is making his own choices. I wonder how LW found out about baby daughter comment and about cheating opportunity. The only regret she might have down the line is not taking all the steps SHE can to protect her daughter. I don’t trust the husband on this one. The daughter and her needs, the LW as a mother–this comes first, before the marriage; at this point protecting the daughter falls into the category of things she can and must control.

    1. Avatar photo Skyblossom says:

      I agree about protecting the daughter. Since the dad isn’t doing it the mom must do it by herself. The LW needs to document everything. If they end up divorced she needs to be able to make her husband’s visitation with the daughter contingent on Jack never being around the daughter. If they stay married the LW needs to warn her daughter from a young age that she can’t trust Jack and should never be alone with him and should never accept help from him or a ride from him. When the daughter is a teen the LW needs to tell her daughter that Jack has said that he wants to have sex with her and that she should always avoid him and should never trust him or be alone with him and doesn’t ever need to feel like she needs to be polite around him.

      Jack is talking about the daughter like he is a predator. He feels comfortable helping himself to his friend’s daughter.

  12. Avatar photo Skyblossom says:

    I think Jack sees himself as the alpha male and an alpha male needs beta males to be alpha. He needs to have guys in his life that he tells what to do and they do it. Jack introducing Don to the LW was probably Jack providing a sex partner for Don which was also a way to control Don’s sex life and make Don’s sex life dependent on Jack’s supplied women. Don broke the “rules” by falling in love with the LW and getting married. Jack probably hates that. He needs Don to be his sidekick. He needs Don to be dependent on him. He is trying to get back to the control of Don’s sex life by supplying him with women which would also have the bonus of breaking up Don’s marriage. Even the desire to have sex with Don’s daughter could be a way to get the LW to pack up and leave and take herself and her daughter far away which would leave Don available as the beta male.

    I think if the LW went to counseling she could explain Jack and Don and the counselor could give her advice on how to handle both of them.

  13. This isn’t so much about Jack in my opinion. This is about the husband’s poor judgement. I would have a hard time to estimate and admire and trust a partner who hangs out with a guy making such statements and acting like this. This is totally unattractive in a husband. The LW is right in my opinion. This Jack must go away or she goes: it is on the husband to make a choice, and he won’t hesitate long I think.

    1. See I don’t know. My husband had a friend who was a total arsehole to me the first time we met. Me and husband had only just started dating and I’d told him to go have a boys night but for some reason friend insisted I come have drinks with them. So I went and the guy was an absolute nightmare. I’d just been at a marriage equality march and his first words to me were “so I hear you were at a f*g rally?” It didn’t improve from there. From what I know they don’t speak any more but it did kind of boggle my mind they were friends in the first place. I think overall I would have been ok with them hanging out without me if it had continued, but you’d have to be with someone you know is more or less immune to serious peer pressure.

      1. dinoceros says:

        Yeah, but apparently his husband either isn’t immune to peer pressure or he likes participating in the things that the friend does. I think there’s a difference between being a jerk and trying to break up your marriage/making sexual comments about your baby.

  14. LW, my husband has this same kind of friend. Mine is a racist more than a player but same problem. My husband was a late bloomer in High School and this guy had a ton of bravado and confidence. This guy did tell my husband that he should divorce me because I couldn’t have kids. It has be about 10 years since i refused to see him. They text and speak every once and awhile but he slowly faded away. The way this happened was that my husband realized he couldn’t bring this friend around to our current friends. It just became harder and harder to see him as our life filled up. I would just chalk it up to not want to give up his past and nothing more.

  15. Stilgar666 says:

    I am the bachelor (32), that friends call for a guy’s night out or vacation. But I am also friends with the wives and trusted with the kids. None of my buddies would ever allow me to negatively effect their marriages, and would punch me in the face if I said anything so gross about their little girls.

    The wives know the husbands will drink more and do some drugs at a concert (I am designated driver, don’t drink anymore), but I am welcome for family dinners, kids birthdays and holidays. We all grew up, some more than others (obviously). Reliving the college days is fun occasionally, but it sounds like this happens a lot.

    Jack has already proved what kind of man he is multiple times. Don should get some counseling, in addition to some marriage help.

  16. baccalieu says:

    I agree with Wendy’s pragmatic approach. (Especially if hanging with Jack is a two or three times a year thing and not two or three times per week). It’s not that Jack doesn’t deserve to be cut out of their life. He’s done plenty to deserve that.
    However, Don has already shown that he’s is not prepared to drop Jack just because she asks him and therefore really her only choice is to separate from him (By all means you can try counseling, but I suspect that Don either won’t see the need to go or if he goes will refuse to drop Jack. I would love to know how Don defends his friendship with Jack. I think it’s likely that, as Northern Star says, he will say that Jack is only joking around and doesn’t mean any of it.) I think that just an ultimatum will not be enough because Don will promise not see Jack and then continue to do so. At that point, she has to follow through and separate or just give up.
    If she’s not prepared to use that nuclear option, then all she can really do is try to set some boundaries. I would also point out that since she broke off with Jack over his actions toward her friend, Jack sees her as the enemy, and a lot of his actions, comments and interest in hanging with Don probably come from a desire to get back at her and get under her skin. If she doesn’t react or reacts mildly (e.g. “Go ahead and hang with Jack occasionally if you want to, just don’t bring him around me or our daughter and don’t talk to me about him or what he said or did.”) If Jack’s antics stop getting a rise out of you (if only because you are not getting to hear about them) I suspect he will tone it down.
    Otherwise, if you think this is worth ending the marriage over go ahead, just recognize that that is what it will take to stop it.

  17. I agree that Jack sounds awful, and I certainly understand why the LW refuses to have anything further to do with him. and would prefer it if her husband did not either. But I agree with Wendy that you cannot force him to end this friendship – he is clearly getting something out of it – and, it is not too frequent, it probably is not worth ending a marriage, with children, that is otherwise happy over it.

    I also think some of the commentary about Jack here – horrible as he sounds – is dominated by indignation running away with itself. It sounds like he makes some truly very inappropriate and distastful “jokes” and he is a terrible “player” with woman. I do not think it really is reasonable to assume that he is really ready to rape their daughter as soon as she turns 18 as some seem to be assuming here (though I can certainly see why the LW does not want her to have anything to do with him.) Nor do I think we can assume he was seriously “trying to break up her marriage” even if they felt that way to the LW – we are probably talking about more highly inapprapriate “jokes” and efforts to yank the chain of the husband and /or LW. It’s hard to know of course, because Jack”s behaviour is being filtering not only through the LW, who understandably wants to make it clear how awful he can be, but also through what her husband has told her about his interactions with Jack. But even so, I still think, “charismatic, totally inappropriate, man-child ‘player’ and manipulator” is more likely to be what we have here in Jack rather than psychopathic predator.

    Finally, commentators are right that the husband is responsible for his behaviour with Jack, and the LW should make that clear, and if she wants to stay in her marriage, should discuss some ground rules with her husbadn for handing out with Jack. However, if the problamatic behaviours are as the letter describes, – “drinking to the point of puking everywhere, gambling, and poor decision-making” – and are not too frequent, I am not sure they are the complete red flags some commentators are making them out to be. Unless he is drinking and driving, getting drunk in front of the daughter or gambling at a level that risks the families financial stability, why should he not, as an adult, be allowed to do these things once of or twice a year?

    1. That’s kind of how I see it. Husband hasn’t run out and cheated just because Jack has sent him a few pics and the comment about the daughter, while gross, doesn’t sound like he actually intends to pull a Quagmire. Don’t get me wrong, guy is disgusting, but husband seems to more or less hold his own against him. I’d chalk him up to infrequent disturbance and keep well away.

    2. A man who hangs out with a known scumbag is not a problem ? A man who tried to encourage a husband to cheat on his wife is not a problem ? A guy who talks about sleeping with a baby when she grows up is not a problem ?

      You will fit right in with Trump and his ilk.

    3. Avatar photo Skyblossom says:

      There is no indication that this is only once or twice a year. We don’t know if it happens occasionally or monthly or weekly. We don’t know.

  18. greenapples says:

    Umm…this is really offensive to me. I can’t believe this woman woulf lay all of this out about her HUSBAND and her husband’s a-hole BFF and not feel like she herself should get her head examined for being connected to a guy who chooses to associate with people like that. This is an underage girl who, for years, the a-hole BFF has talked about wanting to sleep with. Shouldn’t there be something illegal about that right there?

    Personally, I’d want to run hard and fast to get away from all these people. I ever heard my husband’s friend talking about sleeping with my daughter? That’s the last time she or I would be anywhere near him ever again.

  19. Bittergaymark says:

    This remains one of the craziest letters ever.

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