(Almost) Dating A Roommate

Thursday | October 5, 2017

Love Letters Dating

(Almost) Dating A Roommate

I’m hosting a Boston screening Tuesday night (Oct. 10) of “Professor Marston and the Wonder Women,” which comes out next Friday. It’s the one with Luke Evans – about the man who created Wonder Woman. The movie has polyamory, comic books, and some other stuff that is very Love Letters. I’m giving away some tickets for the free screening. If you would like a pair, email me at [email protected] with “Wonder Women” in the subject line, and tell me (in 75 words or less) why you and a friend (or date) need a night out. I’ll pick a bunch of entries and notify winners tomorrow. (No purchase necessary. Must be 18 years of age or older and a Massachusetts resident to enter. Entries accepted between 9 a.m. ET on 10/5/17 and noon on 10/6/17.) Also, we’ll chat at 1 p.m. today.

I’ve been sleeping with my roommate/friend of three years for about a year now. For the past four months, we have been trying to work toward a relationship.

Lately, he keeps saying something is off, which I’m confused about because he says I’m the person he’s always wanted, and that I’m amazing, beautiful, and that he wants to be with me.

About three years ago he was cheated on, and that ruined him in a lot of ways. He told me a few weeks ago that he wasn’t over that betrayal – that he was over her, but not what happened. Everyone around us assumes we’re an official couple. I just don’t understand why he’s not capable; if I’m everything he wants, what could be the problem?

He did ask me about my life goals recently, and I told him that because I have an autoimmune disease, I haven’t wanted kids – but that he makes me want them. Could that have scared him? I was also thinking that because we started as friends-with-benefits/roommates, we never got the chance to date casually.

He doesn’t want to hurt me, but I’m just confused because he does seem to want to be with me. But whatever is holding him back is making it hard for him to actually commit. I just don’t know what to do, and I don’t want to give up. I think if we give up now, we will never know what we could have been. At least if I get hurt later, I’ll know we tried everything. I’m just lost about what to do and how to figure this out.

– Hurting Now

This might be a huge, expensive hassle, but the best thing you can do is move out of your home. You are not helping the relationship (or yourself) by remaining his roommate. If you continue hook up and you both decide that you’re all in, the living situation will mess with your pace. If he decides to end things for good, you’ll be stuck sleeping near an ex.

Really, it would be great if you could go on a date with this guy and then go home on your own. It would help to know whether he’d make an effort if you weren’t down the hall.

You should also be clear about what you know you want right now. You do want to date. You do want to find out whether you’re compatible as more than friends. But you don’t know for sure that you want kids – and you have no idea whether you’d want them with him. You’re imagining some new possibilities, but that’s the kind of thing you should discuss with other friends right now. At this point, there’s no reason to raise the stakes.

– Meredith

Readers? What should she do?

Dating