I was 23 years old before I worked up the courage to tell someone I was romantically interested in them.
It was New Year’s Eve, about 45 minutes away from 2014. I had taken a shot of whiskey and committed to a New Year’s resolution of being brave. I asked this boy, my friend of a little over a year to come sit with me outside, and I then proceeded to metaphorically word-vomit all over him for seven to 12 minutes. Though it was cathartic, my shaky confession did not lead to romance.
Three years later, I still struggle to let someone know when I’m interested in them. But I’m trying. I recently got drinks with someone I had a huge crush on in college. After a few rounds I felt emboldened enough to tell them how I’d felt. “Shut up!” he said, “I had a huge crush on you! I just assumed, because of, well, how you are, if you were interested you’d have said something.”
Because of how I am? To most people I meet, I appear to be quite the entertainer. I never feel more myself than when I have a captive audience — whether that’s onstage doing a reading, or hosting a dinner party and telling stories with a glass of wine in my hand. It’s fairly easy to assume that because I’m assertive in one area of my life, I’m assertive in all areas of my life.
But putting myself out there in all ways, all the time, is exhausting. Sometimes, it is nice to stop chasing for a while, and be chased myself.
Outgoing personality aside, I actually have a paralyzing fear of rejection, which has made dating and hooking up challenging. I’d rather come out to my religious, Republican family every day for the rest of my life than chance a person I’m attracted to turning me down. The conversation in my head goes something like this: I didn’t graduate with my master’s degree, get a perfect job right out of school, move to my dream city and find a rowhouse in a great neighborhood within my price range for some silly boy with pronounced cheekbones and good hair to tell me he sees me as “more of a friend.”
Still, I’ve been trying to quiet that voice in my head, and take more risks. So this past winter, when I felt myself slipping into old habits, I decided it was time to be brave. I’d met someone at a mutual friend’s party; he was in a corner talking to a girl with glitter on her face about third-wave feminism.
I was immediately interested and decided to play the Long Game, which leaves plenty of time for my personality to shine through. This would also give me the chance to ensure it wasn’t just some fleeting attraction, but that I was genuinely interested.
We hung out quite a bit over the next few months — almost exclusively in group settings — but we always managed to end up talking to each other. I was so enthralled with him that I would have listened to him talk about the micro-specifics of the Geneva Conventions. Out at drinks one night, when asked what our favorite Cards Against Humanity card was, we both simultaneously said: “Oprah Winfrey sobbing into a Lean Cuisine.” In real life, that might not be a huge deal, but in a romantic comedy, this is when you know the protagonist is about to get some.
Rather than tell him how I felt, in person or over text, I decided to send a succulent in the back of a golden dinosaur with an accompanying note that said: “Hey, I kind of have a crush on you, so here is a golden dinosaur.” It was delivered the next day. And then I waited.
I’d love to say we’re now happily dating, or at least that we made out for a bit. Rather, I looked down at my phone the next day to see a text message: “I don’t know if you saw it in person, but the succulent dinosaur is amazing! And thanks for letting me know how you feel! I really value our friendship. I don’t see it romantically. That was really sweet…”
My initial thought was: I should change my name and move away immediately. After some time, I calmed down and thought, that’s a ridiculous, he should move. After a few more minutes I took a walk, got an iced coffee, smoked a cigarette in the chilly sun of the first day of spring and realized: If the worst thing that comes from telling someone how I really feel is that I learn I am important to them — even if not in the way I’d hoped — then it was worth it.
Whatever the outcome, it was worth telling him how I felt because at least we’ll get the opportunity to cultivate the relationship we are both interested in, rather than the one I’ve created in my head. I’m not sure if it will ever get easy to do, but understanding the value in taking this risk has made it a little easier.