Is it the right time to tell my friend I have feelings for her?

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I have a close friend I've known for seven years. We met in college and have always kept in touch, even when we lived far from each other. We hooked up a couple times when we were both living in the same area, but then I moved away for work. When we wound up living close to each other again, we were back to being just friends and then roommates with some other friends from college.

When our lease was up, I moved back to the city I grew up in and she moved here too. Over the last few months, helping each other move and experiencing the city through her eyes, I realized I really have feelings for her. Maybe I've always felt them and just suppressed it. I know I used to have feelings for her when we were hooking up, but now they're back and I don't know if it's healthy or what to do about it.

I was going to say something, but I set her up with a place to live through a friend of mine, and now one of her roommates is a musician/producer and she's going to concerts with this person. I feel like there has to be something romantic there and don't want to put pressure on her or be weird, but also I have to take myself into account somehow because this whole thing is tearing me up a little bit. I never really saw it until recently, but our friendship has caused problems in my past relationship, as well. People I've dated have felt threatened by our relationship, and when we go out, it's often harder to meet people because they assume we’re dating.

I think something has to change. Do I say something about how I'm feeling? Do I just swallow the whole thing and do nothing? Do I tell her I’m happy for her if she starts dating her roommate, but maybe then we shouldn't hang out for a bit while I figure this out? I care about her immensely and don't want to put pressure on anyone, especially since I was her introduction to this city and social scene and so many of our friends are now the same. But I feel like I have to say something because it's really throwing me for a loop.

– Forlorn Friend

Telling her might take the pressure off.

Here's my logic: if you continue to think about this, stewing over every detail of your past and present, the relationship will be zapped of all joy. Also, you'll decide she's a perfect match for you without any real evidence. If all of this is happening in your brain, your imagination can run wild.

Telling her might feel like the riskier option, but all you’ll be saying is, "Having you here is bringing up feelings – in a very good way. Do you ever feel like this could be romantic? Would you want to try to make one of these hangouts a date?" I wouldn't recommend telling her that you've been into her for years, and that she's ruined dating for you. That’s pressure. All you really know is that you’ve been thinking about the potential here ever since she moved to this city. Stick to the truth.

If she doesn't reciprocate, you can take time if you need it. Maybe her clarity at that point (assuming she offers some) will help you move on enough and see her for whatever she is. That's why telling her soon could be helpful. The more you daydream about possibilities, the harder it will be to get over the fantasy. Working this out with her should help you stick to reality.

She's not dating her roommate, as far as you know. Tell her you're thinking about her in a new way – and keep it simple.

– Meredith

Readers? Tell? How would you talk about this?