Dater X: Crushing On A Friend

Last Wednesday morning, at approximately 10 a.m., I typed an email to my friend, Brown Eyes. I noticed as I was writing that it was taking me an unusually long amount of time to compose a four-sentence email to a friend I talk to at least a few times a week. I also noticed that I was deleting an awful lot of sentences and rewriting them from scratch, trying to make each line just that much more clever.

I hit send, and immediately felt anxious. Five minutes later, I logged back into Gmail, hoping to see a bold line in my inbox highlighted with his response. Naturally, there was only spam.

I checked my email again at 10:10. And again at 10:12. And then it dawned on me: do I have a crush on Brown Eyes?

Now I’m realizing that he’s someone I could see myself in a relationship with. And someone whom I’m attracted to. And to put the whole truth out there: someone whom I ended up making out with the other weekend.

I met Brown Eyes two years ago at a friend’s birthday party. As she introduced us, I instantly liked what I saw—his tall and lean body, his plaid shirt with rolled-up sleeves, his gorgeous brown eyes behind hipster glasses. We started talking and hit it off. “I work up by Times Square,” he said casually.

“Oh, me too,” I said.

It turned out that we worked in the same building. On the same floor. In next-door offices.

It was the first of many coincidences. We also went to the same college, though he graduated several years before I started, and we’d seen at least five different bands at the same venue at the same time.

At the end of the night, Brown Eyes asked for my phone number and I happily gave it to him.

And that’s where things got complicated. Two days later, I got caught up in a whirlwind romance with a guy I can only call Crazy Dude. Our initial connection was so intense that there were tears on the first date, the word “love” used on the second, and a night full of some of the best sex of my life on the third. By the time Brown Eyes texted me and asked me out a week after we met, I felt sure that me and Crazy Dude were destined for … something. I responded to Brown Eyes with a lame, “So busy this weekend. Maybe another time?” When he tried again, I decided to be honest and tell him that I met someone else.

As you can tell by the foreshadowing, Crazy Dude turned out to be crazy. Within three weeks, we were done. I didn’t reach out to Brown Eyes because I thought, Who wants to be someone’s second choice? Well, that and I was pretty depressed about the Crazy Dude breakup.

But for the next few months, I kept running into Brown Eyes—in the hall at work, at bars with friends. We struck up a casual friendship. One night, maybe six months after our first meeting, we started talking at a party. I decided to address the white elephant in the room. “I’m so sorry I blew you off when we first met,” I said. “You met me at the exact wrong time.” I told him the full saga of Crazy Dude, and he told me all about his new girlfriend, whom he seemed happy with.

“It’s totally fine,” he said. “I’m a big believer in fate. I met this cute girl who I vibed with and she happened to work in the office next door—I thought it had to mean something. I was a little upset at the time. But I’m happy we’re friends now. It all worked out.”

I felt a slight pang of regret that I’d made the wrong choice. He was taken at that point.

In the year and a half since that talk, Brown Eyes and I have become better friends. We hang out regularly, usually after work, when we need a drink to decompress from the day. We’ve seen each other through moves, through the ups and downs of our jobs, and through assorted heartbreaks. He’s someone I value greatly.

Now I’m realizing that he’s someone I could see myself in a relationship with. And someone whom I’m attracted to. And to put the whole truth out there: someone whom I ended up making out with the other weekend.

But I’m very hesitant to tell him that I’m interested in more than a friendship. Or to ask him out on a date—something I feel like I’d have to do, since he once asked and I refused. In the past, I’ve always said that I wouldn’t date a friend and risk that relationship unless I was sure. And I’m not sure. Not even slightly. I just have a feeling that maybe we could be good for each other. I could be right. But I could also realize, maybe even quickly, that he isn’t a green zebra. And I don’t like the idea of rejecting him a second time. Not to mention my concern that he may decide he’s just not that into me.

I’ve had two long-term relationships in my life that grew out of friendships. In both cases, after being friends for a while, the guy started to like me, but I was initially very resistant to the idea of being with him. In both cases, with time, I came to see what was amazing about them and decided to give it a shot. I ended up having great relationships with them, both of which lasted for years. This makes me want to fess up to Brown Eyes and see what he says.

But I’ve also had things go the other way. Years ago, I confessed my love to someone who I, at that point, considered my best friend. We were the kind of friends who hung out constantly, talked on the phone for hours, had meals with each other’s families, and knew the insane minutiae of each other’s lives. He’d given me every indication that he was interested—sometimes he’d grab my hand and lace his fingers into mine; other times he’d put his arm around me and pull me close as we watched TV. But telling him that I loved him and wanted to be with him was more like igniting the gas tank of a car than lighting the candle of romance. Things exploded into a fight—of all the emotions he could have picked, he was mad at me for misinterpreting things. I saw the side of him that wasn’t so lovable. We’ve barely spoken since.

It was the last time I’d say my heart was truly broken. And it’s not a situation I’m looking to repeat. Uh, ever. Which leaves me wondering how to proceed here.

I guess in the meantime, I’ll just keep writing Brown Eyes really great emails.