Developing feeling for my close friend: what should I do?

Dear Edahn,

Over the last few months I've started developing feelings for one of my close girlfriends. I have known her for a long time, but we've never dated (we sometimes used to hook up after a night of drinking, but haven't done that in years). I consider her one of my closest friends, one of the people who knows me best in this world, and one of the few people that knows how to comfort me when I am restless. As I have gotten older, I now have a much better appreciation for what I really want in a life partner and I feel like she might be it. I am ready for a serious relationship, ready to find my lifelong partner, and I've started to love her in a whole new way, as I think about what a life with her might be like. As I've developed these feelings it has been hard for me to hear about her dating other guys, conversations that never used to bother me. I find myself getting jealous and sad when I hear that she is into somebody else and am admittedly relieved when it doesn't work out. I am afraid that I am going to lose her.

I want to know if she would be open to dating, but I'm afraid that if I make a move or if I tell her, it will ruin our relationship. I know that we will still be friends if she doesn't want to date me, but I also know our friendship will change once she hears that I have started developing deeper feelings for her. I know that she will be more guarded and less free in our friendship. It feels so risky to try to explore these feelings I've been having, and I'm even worried that I'm only having them because it is holiday season, I have entered my 30s, and I am going through a period of life-crisis anyway. How can I explore my own emotions to tell if my feelings for her are genuine or just an idealized projection or hope? Should I gamble with and risk losing or changing our friendship and tell her how I feel, or should I play it safe, put my feelings away and guarantee that our friendship remains intact?

This might sound weird, but I think you have idealized her and fallen in erotic love with that image, but at the same time, I think you truly love the person she is without that idealization. The best way to tell is to examine how you see her. Has your relationship with her changed recently? Have you boxed her into a certain persona? Is it harder to relate to her now? Do you find yourself more self-conscious around her? If so, I think what's happened is that your life situation and crisis (which is a good thing, IMO) has caused you to think about the qualities you want in a partner (also good), and to attribute those qualities to her very strongly. The qualities that agree with that projection you embrace, and the qualities that conflict with that projection -- e.g., her dating others -- you resist. I think most people do this when they get into relationships. I see it as a form of erotic/possessive/needy love, but not true love. Erotic love is "grabby." It seeks to acquire something. True love is much simpler and much lighter and really just involves kindness. True love is something you shared with this girl for years. You cared for each other, were supportive, had fun, messed (around) with each other, and let your shadow come out -- the part of ourselves that we routinely hide out of shame. True love is something you share with your friends and family. Romantic partners are no exception.

So now what. My advice is to put all this aside for a moment. Just hang out with her like old times. Let the innocent care you shared with her for years come back out and just have fun without internally condemning her and without totally falling for her. Just be cool and be open to having fun and sharing yourselves with each other like you have for years. In other words, go back to being friends. If you notice that your care for her grows and seems like something special and beautiful rather than something confusing and obsessive, then let your intuition guide your decisions: maybe you decide that friendship feels right; maybe you just make a move one day without explanation; maybe you share your feelings and ping hers; maybe you get drunk together and have sex. You'll know what to do because it will feel natural and feel right.

Most importantly, remember to have fun with it and see the humor in your situation, even especially if it seems like a hopelessly confusing mess. ;) Good luck, friend!

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