“My Boyfriend Asked Out Another Woman”

I am 48, a divorced mother of three children, and my boyfriend of six years is 43 and never married. He has lived at home with his parents for the last eight years. His parents work and are self-sufficient. I own my home and support my children.

My boyfriend is very thoughtful and has always been there for me and my children. We have great communication and chemistry, and we enjoy each other’s company. There has not been any talk of the relationship moving to another level, which appears to be fine with both of us. We both have our space, we can build our relationship (including his with the children), and my children and I can keep our routine.

There have been issues because he has very few responsibilities while I have the management of a home, children, and career, causing my time to be limited. His schedule is flexible so he often sleeps in until 10-11 a.m., and works until 7. My need to “get things done” before I can relax and have fun makes him crazy. But my life could easily get out of hand if I don’t manage things this way.

In order to fill his schedule and his need for fun, he joined, about a year ago, a rowing club which is coed. The club members meet several times a week and travel four to six times a year for races. He has enjoyed this group very much. They also like to drink and party into the night after races or after practice. The couple times I have been around the group I found it to be an extremely flirtatious group – sometimes in a juvenile way. (One of the females in the group asked, in a flirtatious tone, if she could move my boyfriend’s “nice, straight, hard stick”, referring to his oar that was sitting on a cooler. I’m not a prude, but what adults act this way?!!).

Shortly after starting with this group my boyfriend met a waitress while out with friends (he lied about where he was), and subsequently got her number and asked her out. She did not respond. He then began perusing online dating hookup sites, and he updated his old profile. He said he never got a response and he stopped within a month or two of looking.

He feels terrible about this behavior and has said I can trust him, that the grass is not greener, and that he was being an idiot. He has been extremely remorseful and introspective about why he did this so that he will not do it again. I never suspected a thing while he was “looking around.”

That was a year ago, and things have been great, but I still have trouble trusting him and I wonder if I am overreacting to his transgressions. Now I am negative about the rowing club and agonize when he is out of town with them or when they have a practice/party. I wonder whom he is texting and if he is where he says he is.

Am I making a mountain out of a molehill? Or even after six good years, are these issues significant enough for me to make a change? I love him, my kids and family adore him, and he is a good man. People make mistakes and get off track, and I want to move past this. The things he did linger in my mind…and I am afraid that the result will be an erosion of our relationship. — Mom of Three

I’m curious as to how you found out about all these transgressions — the waitress, the online pursuing. How do you know how flirty his rowing group is and the specific thing the one woman said about moving his oar? I’m assuming you were there, but maybe that’s not so? Maybe your boyfriend simply told you these things, and then I have to wonder: why? Does he want you to worry? Does he want you to not trust him? To break up with him? To do something to change the dynamic of the relationship because after six years maybe things aren’t as “great” as you seem to think they are (and not for nothing, but a relationship where the boyfriend regularly feels crazy because his girlfriend has responsibilities doesn’t sound all that great or very well-matched either). And maybe not moving your relationship to another level isn’t so fine with your boyfriend. You say it only “appears” fine to you both, which makes be believe you haven’t had a conversation about the state of your relationship in a long time.

If you two haven’t recently (or ever) had the discussion about goals, it’s time. Where do you see this relationship going? What is its purpose for you both? What role is it filling in your respective lives? Are you both having your needs met? Obviously, your boyfriend’s needs were not fully being met, which is why he joined the rowing team (a healthy solution) and why he sought out side pieces (an unheathly solution). What about now? What has changed from then until now? Is the rowing club fully filling the hole that existed? Does he now feel completely fulfilled? Is seeing you in the time you have free after working full time and taking care of your three children and your home enough for him? Is it enough for you to have a boyfriend who shows no interest in ever being a live-in partner and parent figure to your children? If you are perfectly happy having a romantic partner who respects your personal space and doesn’t intersect too much with your family life, is your partner perfectly happy with that?

I suspect what is nagging at you is more than just your boyfriend’s asking for a waitress’s number and perusing online dating sites a year ago and being involved with a flirty coed rowing club. I suspect you also fear that you two simply are not on the same page and that you aren’t in a position to meet his needs. I also suspect that there may be a lack of respect for him on your part. Your boyfriend is 43, is never married, and has lived with his parents for eight years for no altruistic reason whatsoever (his parents do not need him to care for them). Like, what is he avoiding? Likely, all the things you tackle head-on: financial responsibility; home ownership; parenthood. You are juggling so much while he’s … not. Not at all. And rather than use his surplus energy to support you in whatever ways he can, he goes “crazy” when you need to “get things done” before you can relax. That would drive me crazy. What an overgrown man-child!

This is bigger than your boyfriend making mistakes and getting off track. It seems to me the bigger issue is a fundamental difference in lifestyles — and a lack of respect for your differences — as well as possibly differing goals and unmet needs. You two need to sit down and have some serious state-of-the-union talks and see if you can get on the same page, or even in the same chapter. If you want to commit to making this work — and I would think that’s probably a big IF — a compromise is needed. It would behoove your boyfriend to better support you as you tend to your responsibilities, and you would do well to carve more time to join him in his fun-seeking (are partners ever invited on the rowing trips? You should go, not just to share in something he enjoys but to check out the dynamic of the group).

If it were I, I’d probably MOA. A 43-year-old who’s lived at home with his self-sufficient parents for eight years? That alone is reason enough to sayanara on out of there.


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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. Leslie Joan says:

    LW, I’m confused. First you say that the guy is oh so thoughtful and helpful and has always been there for you and your kids, on top of which you have fantastic communication, etc etc. Then you say that he’s got a lot of free time and flexibility which you lack in your job, plus you have to deal with the house and kids, which is a bone of contention between the two of you (“drives him crazy”) that you need to get things done before you can relax and have fun. I just plain don’t see the oh- so-helpfulness the being there on his part. Seems to me he’s like another project you need to manage. If he wanted to make time to have fun with you, he could help get some of your tasks done. He sure has the time to do so, because he hasn’t a responsibility in the world except for his job. Instead he’s nagging at you because you don’t have the same level of freedom. Ugh. That’s not supportive at all.

    I don’t generally like when never married guys get called a man-child, but I have to say that Wendy is spot on. He’s looking to be entertained. And you will never trust him. You would be better off with a partner who is a true equal. This guy is not. However flirty his group members are is irrelevant.

    1. RedRoverRedRover says:

      I don’t think Wendy called him a man-child because he’s never been married, but rather because he’s living with mommy and daddy for no apparent reason beyond he likes having no responsibilities. Calling him a man-child for that reason is pretty fair.

  2. Your letter reads like an attempt to convince yourself that your relationship is working, but your words keep shouting that it’s not working, that the two of you are too different to be compatible. The guy has no interest in taking on any responsibility beyond his very flexible job and wants a playmate. That may have worked in the beginning, but now clearly you don’t have enough time for him to be happy and he is to irresponsible for you to be happy. The trust issue is just an added problem. This isn’t going to get better.

  3. I won’t add to the very good answer by Wendy. One thing strikes me: do you have fun sometimes by yourself, with friends, with a fun class, a hobby or a group, without your boyfriend? You seem to have lots of burdens with work-family-home, and I understand that. But if you go out one evening per week for your own fun, and he keeps the house-makes dinner-surveys kids homework ( if you trust him), or you hire a baby-sitter: this would change a bit the very mother-child dynamic you both have. Feel free to have fun too! Don’t spy on his fun. Turn the focus on yourself.

  4. Bittergaymark says:

    Eh, honestly? Why do you even care? This relationship was over long ago.

  5. jesus- are you dating a teenager? He is not an adult. He doesn’t understand that you have obligations? Fill his schedule? He sounds like a spoiled brat. Reread Wendy’s last paragraph. MOA

  6. dinoceros says:

    In dating, there are various points in time where you make decisions about whether this is the right person for you. Personally, if I met a guy who lived with his parents in his late thirties (for no reason — like not as a caretaker or because he was experiencing an emergency), I wouldn’t really continue. I just wouldn’t foresee the whole “him pulling his weight and living like an adult” thing going well in our relationship.

    I just really can’t imagine staying with someone who asked another person out and started up an online dating profile while we were in a relationship. The really telling part here is that it sounds like he stopped because no one wanted him and his love interest ignored him. What if someone had gone out with him or if she had replied? Who wants to have a boyfriend who is only with them because the other people he started pursuing thought he was a loser?

    The thing is, he’s in his 40s. He is who he is. It’s not like dating a guy who in his early 20s does something stupid and then grows as a person into his 30s. I just don’t really see what kind of personal growth a person is going to do in their 40s to where they go from actively trying to date people while they are in a relationship to being totally trustworthy. And it’s not “in the heat of the moment” kind of thing — like he spent at least a month pursuing other women. There’s a reason you don’t trust him. I have no clue why you’re still with him.

  7. Ohhh I’m a long time lurker but a letter about dating a man-child rower is so up my alley I couldn’t resist. First of all, rowing and not crew? You’re UK based? But then you said coed instead of mixed and now this a great mystery.

    Second, as a female rower I can testify that it’s a flirty, competitive, juvenile and narcissistic atmosphere. No, of course not everyone is like that and I would expect that at 43 you grow out of some of it but I’ve been proven wrong. I wouldn’t get too stressed about the “lad” culture if it stays at practice, boathouse and related socials. It’s kinda unavoidable and as long as he doesn’t bring it home, ehh… The “nice, straight, hard stick” innuendo is so ridiculously common, don’t put too much thought on that. Yes, it’s stupid and immature (and leads to so much sexism in the sport) but it wasn’t your boyfriend saying it and you’re not trying to fix the sport anyway. That’s not your main problem, right? I would guess that you don’t like the lack of focus or ambitious. Because that’s what it feels like from your description! A guy who wants to fool around, not because he doesn’t love you but because he’s an idiot following his dick is a guy who doesn’t think much about the future, or anyone else.

    Third point, he said that he “tried” for 2 months or so before giving up. That’s a lot of trying, not just a momentary lapse in a bar while slightly drunk and horny. What do you think would have happened if the waitress or the online dating women were interested? Would he have stopped and felt “extremely remorseful and introspective about why he did this so that he will not do it again”? What kind of letter would you’ve been writing?

  8. SpaceySteph says:

    A guy who asks out a waitress is a slimeball. Simple as that. A waitress is just trying to make a living and because she relies on tips has to pretend to be nice to whatever grody guy is slobbering all over her because telling him where to shove it will result in no tip.
    If I knew nothing else about him, I at least know that he is a slimeball. Dump him.

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