Lessons learned from when the first boy I ever asked out said no

Beautiful dress? Check. Laughing with friends? Check. A time-of-your-life-post-dance high? Check. Boyfriend? Not so much. On the night of the Winter Dance, I felt bold. I took a deep breath, and asked the boy I had been crushing on for months if he wanted to go on a date (yes, it was via text. Cringe.) He said no.

I had all of one boyfriend in high school—a charming, (older!), self-deprecating writerly type who was dangerous without ever actually requiring caution. By the time I had changed schools, and states, right before my junior year, he had gone to college and I had to start over. I was always just within reach. Not popular, but I knew everyone. Had boys who were friends, but not boyfriends. I was the girl who was opinionated and loved school.

When I think about it now, I am not really sure what drew me to him. Maybe it was the fact that he was very laid-back (something I’m not), and was kind to everyone. Or maybe it was because he was cute, and sixteen year-old me was into cute, I’m not sure. But what I was sure of was this connection we had. Flirting in class, making dumb jokes, and talking about life over group projects.

So after the dance, feeling brave and confident, I texted him. I built slowly to the question, beating around the bush and grasping for excuses to the keep the conversation going, all the while wondering How do guys do this ALL the time?. Then finally I did it. I asked him if he’d want to get dinner sometime.

I remember being in the backseat of my friend’s car, driving to her house for an after-dance gathering, and feeling as if I was literally sinking into myself. That if I looked at the phone any longer, I would completely disappear. I wished I could disappear. He was polite, but very clearly let me know that I had it all wrong. Months of interactions played over in my mind, re-writing what I thought was flirting into a one-way, embarrassing display of naiveté. Had I been making a complete fool of myself all this time? How could I have ever thought he would be interested in me? What made me think I could ask him out? I took a giant leap, and had fallen flat on my face.

Seeing him in school the next week was painful. I was mortified, and worried that somehow people would find out, like when you told your friend you liked a boy in elementary school and he and his friends made fun of you during recess. But he was kind, and didn’t treat me any differently. I realized that I was the only one who felt weird. I had to shake it off.

It took another year or so before I asked someone out again, but the experience was certainly transformative. Once I finally did get over the awkwardness, it was a revelation: the worst that could happen is he could say no. Did it suck? Yes. But only for a short time—much shorter than the amount of time I would spend obsessing over whether a boy liked me too. All this time, the answer was so simple; I just had to ask.

The first few times I asked someone out, it was brutal. Even when they said yes, the whole ordeal involved a lot of self-pep-talks, and nervously held breaths. Yet, just like with anything else, with practice it became easier, rejection stung less, and the thrill of it all was kind of fun. If I had to estimate, I’d say I have probably had around a 40 percent success rate—partly because I was going after the wrong guys, and partly because I had misread a situation.

Yet simply having the knowledge that I could ask someone out, and that everything would be okay, maybe me more confident in my dating self, and gave me much more respect for the guys that asked me out. It’s tough! Understanding that vulnerability made me a better a date. I didn’t let the fear stop me from going after what I wanted. And in the end, it worked out: I made the first move on the guy who I later married.

(Image via iStock)


I’m 22 and never had a boyfriend–and that’s ok

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