‘He can’t do anything more than dinner and hooking up’

I am in my 40s and dated a guy I met on online for almost a year. That was five years ago. We were both finalizing the details of our divorces at the time, but we fell in love with each other. I was drinking – a lot – to numb the pain of the divorce. The drinking caused issues with our relationship, which lead to the breakup. At the time, he was an excellent boyfriend and said he was very used to relationships and typically always in one. He did all the right things: nightly check-ins, weekends away, dates out with his friends, and we met each other's kids. It was all good. But my drinking ended it.

Fast forward five years. I've stopped drinking and have managed to get my life into a really good and healthy place. I ran into him earlier this year and we began communicating again. Since then, we have been texting a lot and have seen each other a few times. We still have a great chemistry, and he is the kind of man I would like to end up with.

He has told me that anytime I want a "booty call," he'll be interested, but that he can't do anything more than dinner and hooking up. He says he does not want a relationship with anybody. He told me he has a lot of people who need things from him and drain him, including his ex-wife, his kids, and the people at work. I think he can't handle any more people depending on him, and I think the last few girlfriends he dated (myself included) were sort of trainwrecks.

I want to be the easy-breezy one who says they can handle just dinner and hookups, but the truth is that when I see him, I just want to see more of him. What do I do?

– wanting more


It's difficult to separate what happened five years ago from now, but you must. Yes, you were responsible for the end of the first round of your relationship with this man, but that chapter is over now. You have to make decisions based on what he's offering in the present.

For that reason, you can't pretend to be easy-breezy. You can't smile about seeing him every few weeks if you're wishing he could offer more. (I mean, you can pretend to be cool about all of this, but it will make you miserable.)

You need to let him know that you want more than hookups – and to see him more often – and that if he's not in that place right now, you'll have to move on. It will be difficult to walk away, but your first priority is to be good to yourself.

Also know that it would be nice to be with someone who doesn't think of romantic relationships as a drain. Some people want a partner because a good relationship can be a boost. That's the kind of significant other you need.

– Meredith

Readers? Should she try to be breezy? Is he tentative because of their past?