What I learned from dating my high school bully as an adult
When I agreed to go on a date with the guy who, I had every reason to believe, hated me in middle school, it was hard to conflate the image of a scrawny, buzz-cut pre-teen in a baggy white T-shirt and a silver chain necklace with the streamlined, sandy-haired, button-down-donning—well—man who opened his door to me that evening.
I was late, because I was nervous, and he seemed equally so as he awkwardly showed me around his house before we walked through the chilly, pre-Christmas air to a nearby sports bar to watch the city’s professional football team play on eight big-screen televisions. Later that evening, when he drove us to a deliciously gaudy area of town, done up for the holiday with so many strings of colorful lights and inflatable snowmen that it was likely visible in a few satellite photos, I slipped my arm through his elbow nook for warmth and contact, and felt overwhelmingly happy. I playfully placed my free hand over his mouth when he loudly exclaimed how and why he’d stopped believing in Santa. “There are kids here!” I said, bumping into a few. It was crowded, and everyone and everything seemed to be pushing the two of us closer. It was kind of perfect—cold and warm at the same time, like a homemade brownie topped with ice cream.
But, a few hours later when he walked me to my car, he didn’t kiss me. All of my worst fears were confirmed. He still thinks I’m hideous. This was all a cruel joke. And the whole drive home I relived the conversation I had with my mom every night in the 7th grade. Because I used to cry and shake and whimper that I couldn’t go to school tomorrow. I couldn’t face the boys who made me feel so awful. The ones who sneered and laughed from the next lunch table over, who said no one will ever want you, who all took their lead from the scrawny, buzz-cut pre-teen who turned into him. My mom used to rub my back and lie down beside me and say, “He likes you and doesn’t know how to show it.”
The next day, he asked to see me again. I was shocked, but agreed. The following weekend we shared an evening consisting of dinner at a nice restaurant right on the harbor, wine, and lots of laughing. I told him how I remember in fourth grade, on Teacher Appreciation Day, his mom came in to deliver the gift he was too embarrassed to present to our teacher himself. It was a mini, potted herb garden with a handwritten sign that read, “Teachers could use a little more thyme.”
I gave him a copy of my favorite book and he kissed me. It was lovely but also kind of like a middle school slow dance: sweet, clumsy, careful. Over the next few dates I realized that we both unintentionally acted twelve around one another, even though we were now in our mid-twenties.
When he told me he wanted to make us dinner on Valentine’s Day, but not for Valentine’s Day, because he didn’t want to celebrate the holiday, I was relieved. “I like you, but we won’t need to do that, right?” he’d said. It seemed like a lot less pressure—until he put a small box on the counter and I was horrified and excited at the same time. I opened it and he laughed: it was my own necklace, one I’d accidentally left behind the week before.
Later that night, he walked me to my car that was parked a few blocks away, by then encased in snow and ice, and said goodbye. As I scraped my windshield to no avail, then tried sitting and waiting for an effective defrost, I wondered if he’d thought for a second about leaving me alone on a city street at 1 a.m. in a snowstorm. I wondered if he knew he was being a little jerky—if he’d ever known. Then, with my radio and my gloves on, my doors locked and still waiting, I remembered that time in high school when he’d made up a nickname for me in the boys’ locker room before baseball practice. I had been so mortified that mention of me had been uttered there in any context that I came home and told my mom. She’d said, “Hey, you’re amazing. And him? Don’t let anything he says or does bring you to tears again.”
One night, I overheard one of his friends refer to me as his girlfriend. I couldn’t decide if I liked the way it sounded because of history, or because of the present. I also couldn’t decide how twelve-year-old me would have felt about it all.
Then, he met my mom. He came to my house to pick me up and took me to dinner in the little hometown we share. We saw our seventh grade teacher in the parking lot of the restaurant. She had been my favorite, with her curly hair and perfect chalkboard cursive, and I couldn’t help but imagine what she would have said had she seen the two of us together. But she didn’t see us; she drove away too quickly.
As he took me home, he pointed out the tennis court where he learned to ride a bike. I imagined little him, theatrically breaking out of his training wheels, turning tight figure eights and occasionally bumping into the fencing. In my driveway, we quickly kissed goodbye, then I spent the rest of the evening crossing my eyes to see the small smudge his nose had left on the bottom of my glasses lens, listening to my mom exclaim how she couldn’t have picked him out in a crowd. My phone buzzed before bed with a text that said, “You’re amazing.”
By the start of spring, he’d grown more distant, and that seed of self-doubt planted inside me fifteen years before was in bloom. But it was actually kind of beautiful. I told him it was OK, we didn’t have to see each other that way any more, we could stay friends, and he didn’t have to feel bad about it. I handed it to him on a platter, breaking up with myself. I didn’t cry, not at all, because my mom had presented me with all the evidence from the past and the present: he liked me, he just didn’t know how to show it.
In the end, I’m glad we tried, and I’m glad to have gotten to know him on a different level—one that almost, almost made sense of what had happened growing up. I can finally let go of the negative feelings I’d carried with me into adulthood. That’s a gift I can give to myself. Along with this knowledge: It’s worth giving people second chances.