Dear Katherine,
A few months ago, I moved in with a group of strangers I met on Craigslist. I like living with them, but there’s one problem: I’m in love with one of my roommates. Despite my better judgement, I drunkenly hooked up with him shortly after I moved in. I know it was casual, but now that I see him every day, eat with him, talk to him — I’m starting to really have feelings for him. I feel comfortable around him and I can talk to him about anything. I have told him about this (in a drunken rant, of course) and he says he does like me but doesn’t want to get in a relationship with a roommate. I understand where he’s coming from, but I just feel like this could be something great, regardless of the fact we live in the same house. The circumstances aren’t the best, but if you like each other, you like each other, and that’s all that matters, right?
Sincerely,
Roommate Lover
 
Dear Roommate Lover,
The hesitations of getting involved with a roommate are understandable. What if it didn’t work out? It is a delicate situation and you have to truly assess whether it’s worth the risk or not. Just like you should do in any relationship, you have to sift through your feelings and make sure you want him for the right reasons  — i.e. not just because you’re lonely.
However, I’m a firm believer in the power of risks between two people who have a connection. Ever heard the saying: “To love is better than to have not loved at all?” When two people truly connect with each other, the risk is worth taking, no matter if you live apart or live together. How often is it that you find someone who you can really talk to and be yourself around? When you truly like someone, using rationalities, such as “I don’t want a long-distance relationship,” “I don’t want a relationship with anyone at the moment,” or, in your case, “I don’t want to get involved with a roommate,” seems to be an excuse for a lack of feelings. It’s mature to be aware of the possible consequences of the situation and weigh the pros and cons, but when love is there, the risk is a no-brainer. You really like him, and you’re willing to take the plunge. If his feelings were as intense as yours, wouldn’t he?
Besides, if your roommate was really against roommate romance, he should have considered that before he hooked up with with you.
Sincerely,
Katherine