My advice: Do it. Ask.
Here's a story. There's this woman I've been friends with for years. I had a thing for her back in college, but got over it, and we've remained very close friends. In the last year or so, I've realized I still have feelings for her. We've been talking more lately, and so the other night, I just flat out said it. "Is there ever a chance that there will be anything more between us?" She said, "I don't know. Honestly, I just don't know."
This actually made the next step even easier for me. If she had said "no", then it's obvious. If she had said "yes", then it's pretty obvious as well. But with her reply, I simply told her, "OK, look...you know how I feel about you. I can't NOT feel that way. But I can't make you have feelings for me either. I would love to have a relationship with you, but I'm not going to wait around forever for you to magically have feelings for me. You know my stand, and either way you will always be one of my closest friends. Let me know if anything ever changes."
I've gotten an email or call from her every day since.
Life is short. Ask. Force the issue. Don't fuck around.
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