How Do I Handle A Guy’s Overbearing Mother? Ask A Pro

Head Pro thinks you’re very mature for your age and wants to hear way more about the last EDM festival you attended. Email him at and buy our dating advice book.

Dear head pro,

I’ve been dating this guy for a few weeks and things are going well so far. He was previously engaged a year ago, but that fell through. On our first date, he told me his mother was the reason the engagement ended, stating his fiancée always picked fights about his mother not respecting her. Another thing…he is 38 years old and I’m 23. Should I continue dating him despite the possibility that his mother may never cut the cord, or ditch him? Help.

Ain’t yo mama

Christ, no. That is a fucking nightmare that you don’t want any part of. Now, it’s possible that his mother is a fine, upstanding older woman who looks really good for her age and the ex-fiancée was as BSCB, but that’s not much better. It would also require the mother not being overly protective of her still-unmarried 38-year-old son, and the ex putting more emphasis on respect than a 90’s West Coast rapper. Which do you think is more likely?

Also, while I’d like to think I’ll still be tantalizing to nubile 23-year-olds when I’m 38, my larger thought is that I won’t care, because I’ll be doing slightly more adult things. Like, as it is I bet your idea of a good time is different than mine, and those trajectories are more likely to further diverge than converge.

The age thing would be fine, and the mother thing might be doable, but everything combined is too weird for any reasonable person to handle. I know it’s nice to date a guy who can afford to take you to places with actual glassware, but I would abort.

Hi Head Pro,

I met this guy about a month and a half ago through OkCupid. He’s a really good guy, we have some similar interests, and he’s by far the best guy I’ve ever been with in bed. So what’s the problem? Well, I like him a lot, but I don’t feel anything stronger than that, and I don’t think I’m going to in the future. I know dating someone for like 6 weeks isn’t very long, but I’ve had two serious relationships before, and both times I was crazy about the guys by this time. With this guy, I’d be kind of bummed if we ended things, but I feel like I’d be over it by the next day. I really enjoy spending time with him, but I just feel like there’s someone better out there.

We haven’t had any exclusivity talks or defined the relationship, and I’m in no hurry to do so since I don’t know what I want. I’m not sleeping with anyone else, but I have gone on other dates since we met. I can see that he goes on OkCupid every few days, so for all I know he could be having the same conflict about me, although he has made some comments that make me think he may want to be more serious, or at least keep dating for awhile. I try to be open and upfront wherever possible, but I can’t think of a way to say “I like you, but I want to see if something better comes along” without being the world’s biggest asshole.

A lot of my friends have been telling me to just wait it out and see where it goes, but I’ve never done this sort of non-exclusive dating thing before, and I’m not sure if it’s for me. This past weekend, I had a really nice date with him, he insisted on paying for everything, in bed he made sure I came multiple times, then I went home and set up a date with a different guy on OKC. Even though I know it’s not technically wrong, I just feel kind of crappy doing things like that.

I’m a big planner, and I think part of my problem is I’m trying to predict the future when that’s not possible, but I’m just not sure what the right move is here. It seems stupid to end something when it’s going well and there are no problems, but I’m afraid of a) leading him on then hurting him b) settling because it’s comfortable and having regrets later or c) missing out on maybe meeting someone better because I’m with this guy.

Should I stay or should I go?

I say you stay, at least until someone better comes along. Part of your conflict is the lack of spark, and that’s understandable. But on the other hand, you’re 26. That’s not to say getting older means you’re consigned to a vanilla, ho-hum love life, but at the same time it might not be reasonable to expect the same kind of fireworks you experienced in your teens and 20s, when shit was a lot newer.

And you said it yourself—you’re a planner. Presumably, your other relationships ignited sparks because they somehow defied your expectations, but then again you’re not with those guys anymore, are you? The problem you’re facing now is that while this guy obviously checks off all the boxes you’re looking for, I’m assuming you’re also “planning” for your love life to be spontaneous and exciting. Those two things are not and cannot be compatible.

So keep doing what you’re doing. If you both seem to have the same mild apathy for each other, that’s fine, you don’t have anything better to do. And if someone more exciting comes along, that’s great too. I don’t think you need to worry about leading him on and hurting him, because you’re actually dating, not insincerely hinting at the possibility in the future. The latter qualifies as leading on, the former just describes pretty much every relationship that goes on for a while, then ends.

You might, however, consider hanging back on OkCupid for a while. He can see when you go on too, you know. 

Head Pro thinks you’re very mature for your age and wants to hear way more about the last EDM festival you attended. Email him at


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