If you want to see today's newsletter (which has pics from the party), it's all here, I think.
I'm living in a shared apartment with six other people. Last December, this guy "Steve" moved in. At first I voted against him as a roommate for some reason I don't remember anymore. But he turned out to be one of the funniest and coolest guys I've ever known. We love the same music, we love going out, and we are both very easygoing and share the same humor. He's three years younger.
As we got to know each other, I developed feelings for him. And they are not just physical. One time we had a "moment." We went out with our other roommates and got drunk. After the others left the bar, we stayed a little longer and then walked to the bus. Somehow we ended up in each other's arms. I tried to kiss him but he denied me, saying he would like to kiss me but had concerns about the flat share and us living together.
The next day I talked to him, "clarifying" that this was just some drunk move and that I always get clingy when I'm drinking. I added that I don't have crush on him (breaking news: I was lying). But after that, we got even closer. We started to watch Netflix together and talk a lot more. I felt a kind of intimacy growing between us. We started talking about love, if we had crushes at the moment, and I told him about my past. I believe that my feelings are real, and I'd really like to just kiss him. I do not only want sex. I want something deeper. At the same time I know that it won't work out because we are roommates. I don't know how to read his behavior toward me. He likes to tease me a lot, always keeps me company, and talks to me about very deep topics. Do you have any advice for me? Should I act on it or let it wash away?
You write about a fear of ruining what you have, but it sounds like the status quo is kind of uncomfortable. It also sounds like it's time-consuming; this roommate/crush is becoming your most important companion. It can't go on like this forever.
Your best bet is to make a decision and then go with it. If you decide that he's just a roommate and that this shouldn't happen, force yourself to change your routine so that he's no longer the central part of it. Make plans with others. Spend more time outside of the house. Do what you'd do if you had an unreciprocated crush anywhere else. Basically, take as much space as possible.
If you know you can't let this go (breaking news: I don't think you want to), make your move. Do not confess love or anything monumental. You explained it well in your letter, so work with that. "I have feelings, and I'd really like to just kiss you." If Steve is still concerned about the living situation, talk about how it could work – or not. Let him know that no matter what, you want him to be comfortable in his own home. That said, if something – or nothing – comes of this, you'll need a new set of boundaries.
For the record, I do know plenty of couples who started hooking up as roommates and then became serious about each other. I don't want to get your hopes up, but when feelings are strong and important, people figure it out.
Readers? Is it time to talk about these feelings?