“Mary” and I have been friends for eight years. She’s one of the only people I’ve ever thought really got me, and I’ve always felt close to her. I knew Mary had a crush on me in high school, but I didn’t reciprocate and we kept things friendly. We now live in separate states, but still talk almost every day. Mary and I have both had a rough summer. She broke up with her boyfriend after a 3.5 year relationship, and I experienced a lot of career setbacks. I think we really helped each other out, and we got really immersed in each other.
Not long ago, Mary told me she was in love with me and wanted to be with me. She said she’d always felt that way and believed I was “her person.” At first I didn’t know what to make of it, but I realized I might reciprocate her feelings. I care about Mary immensely, more than anyone else, and always find myself looking out for her. I feel like I can talk about anything with her, and I do think she’s cute. I’m not very good with my emotions, and I don’t know if it’s love that I feel, but it’s definitely something and I don’t think it’s the same as before. On the other hand, maybe I’m just flattered to have someone who likes me and is attracted to me, which is unusual, and it has helped me feel better after my personal disappointments.
I really don’t know what to do from here. Mary obviously wants us to go out, but I’m not sure that’s a good idea. First, just practically, we live nowhere near each other and probably won’t anytime soon (she also has a great new job that I’m super proud of her for having that I don’t want to disrupt. Second, I’m concerned that my feelings are in flux, or I’m forcing myself to feel a certain way. Third, I’m worried that if I go out with her, and things don’t work out, then she’ll be really badly hurt. Finally, Mary and I disagree on how compatible we are. We’ve been there for each other and clearly care about one another, but it seems like we want totally different things out of life (she wants a normal life and kids, I want to be at the top of my field and may never have kids). She thinks we’d be a perfect fit, but I’m not convinced, and it seems wrong to start a relationship that I’m already not sure will work. At the same time, I think I want to go out with her, and she’s convinced I’m over analyzing things.
I really care about Mary, and I may even love her, but more than anything I don’t want to hurt her or waste her time anymore. I don’t think we could possibly go back to being friends, especially since she’s clearly never thought of me as a friend. So I think it comes down to whether I should I go out with her or let her go entirely?
TLDR: my close friend has loved me for years, and I may love her too. If I shouldn’t date her, how do I avoid hurting her?