So, I have a bit of a dilemma. This woman—we’ll call her Margaret—and I are wonderful friends. We met a couple of years back at an old job. The first couple of times we interacted one on one were actually dates, but she ended that after a couple of outings. While I was attracted to her, I understood, and there were no hard feelings.
After a very brief break in communication, we started to hang out as friends. It became clear almost immediately that we were very compatible as friends. We’ve been close ever since, and I get along with her better than anyone I know. We never really talk about our initial and brief attempt at dating, other than awkward jokes and her occasionally apologizing for the way it was handled (though she handled it perfectly fine, in my opinion).
We did, however, talk about everything else, from other relationships to life goals to whatever else you could think of. While I must admit I held onto a minor crush throughout the friendship, it was nothing that I couldn’t set aside—it never really brought out any jealousy or negative emotions, and I was perfectly happy with her as a great friend. Everything was great.
Earlier this year, she moved up north for school/work/family purposes. We were both bummed, but promised to keep in touch and visit. While the communication has obviously dwindled a bit over the last six months or so, we text frequently and call every so often. Last week, I had the opportunity to go to a town very close to where she had moved, and I immediately took it. Long story short, we had a wonderful time. We spent days exploring the city, eating fancy food, getting drinks and talking nonstop. It was amazing.
The only problem came when it was time for me to leave: I was devastated. I realized almost immediately upon getting on the plane how much I missed her and how much I wanted her in my life. She’s essentially everything I’m looking for in a person, and it took being away from her to realize it.
Is there any reason at all for me to bring this up to her? I respect her feelings and don’t want to push her, and if she doesn’t feel the same way, I will most likely mess up one of my most cherished friendships. And while I feel—based on comments recently and in the past—that there is a chance she may share these feelings now that we’ve grown so close, I don’t even know what that would mean at this point. She lives quite far from me, and I don’t know how plausible it is that we could make anything work.
I feel like I’m going to explode if I don’t tell her, but should I just keep my mouth shut? I’d really appreciate your help on this.
Your and Margaret's first attempt at dating is what I'd call a “false start.” You tried during a time that wasn't ideal, but that doesn't mean you can't try again. Your years of friendship have given you the opportunity to really get to know each other, and honestly, your letter reads like a script treatment for the only rom-com I'd be willing to see in a theater this summer.
You are in love with her. It's my opinion that she has strong feelings for you, but it's gonna take asking to figure out if they're platonic or more. My sister's husband currently lives in Scandinavia, she's here in Athens, and they spend their days emailing, Skyping and organizing beautiful whirlwind vacations while his immigration application is processed. Please, don't be intimidated by the distance.
My advice to you is to spill your guts to this woman. Don't assume that you'll lose the friendship, either—I have plenty of friendships that are the results of my own ham-fisted dating attempts. Go get your boo, then write a book about it. This is incredibly cute, and it warms my heart.