Attached To Mike

This letter seems to be about Mike, but it's also about learning to prioritize a fiancée. In other news, I think it's time for updates. Former letter writers: Please send updates about your situation to meregoldstein at Let us know if our advice was helpful. Let us know how it all turned out. Please use or include your original email address so I know it's really you.

My roommate Mike was in a long-term relationship with a woman, but he had a brush with the law and she left him while he was in jail. Now his life is totally different. That brush with the law has ruined his job prospects, which means he works long hours in low paying jobs trying to make enough to scrape by. He is lonely and tried to find a girlfriend but they either don't fit his preferences, or they end up not being interested. He's in his 30s now and feels hopeless, so he figures he will just live with me forever.

I have other plans for a future with my fiancée who is finishing grad school next year. I want to be a supportive friend to Mike for years to come but he will need his own life too, and he really believes that it's never going to happen for him. I have told him he needs to go to therapy to deal with the jail time and breakup, but he hasn't because he doesn't have the time, money, or motivation. He also has some dating practices that aren't working in his favor, which I have pointed out to him — the long list of physical preferences; some well-intentioned but over-controlling tendencies (he's "traditional"); the tests ("I called her five times, now she has to call me in the next 24 hours to prove she likes me or I'm going to assume she never liked me at all") and so on. How can a guy like him find the right woman if he isn't willing to compromise, relinquish some control, or face his own emotional issues? Does he really not have a chance at the traditional life he wants?

– Not Interested in Being Joined at the Hip

I can't predict Mike's future. There's probably some woman out there who will put up with his rules, but who knows if he'll find her.

But that's not why you're writing in, right? You want to know whether you're allowed to break up with Mike. And the answer is yes.

You must prioritize your relationship with your fiancée. That means telling Mike that he has to fend for himself and find his own place. Let him know you'll be there for him as a friend – you'll even help him research ways to find affordable therapy. But you won't put your own relationship at risk. You also won't spend more and more time on his problems if he isn't willing to get help to face them.

Saying this stuff doesn't make you a bad guy, especially if you let him know that you do care about him and want him to be happy. Work with him to come up with a plan for a new living arrangement. Understand that the minute your fiancée finishes grad school, you'll need to work with her – your real partner – to figure out what's next.

Readers? What will happen if he stays with Mike?

– Meredith