Why I’ll always be grateful for ‘the one that got away’

The first time I felt my heart peek its head up beyond its friend-zone borders with a guy we’ll call Henry was in the parking lot of the grocery store where I worked. It was the summer of 2003; we were 18, and had just graduated high school. He was teaching me to drive stick shift in his beat-up green Saturn that had a Bigwig sticker on the back windshield so huge I could barely see out of it. I sucked. But he assured me it wasn’t a big deal, since it was two in the morning and the lot was deserted. He also told me he’d never let anyone drive this car – not even his mom. That was the moment I knew I was in love with him.

But it was hard not to be. Twelve years later, I suspect a lot of girls felt that way about Henry. He was tall, but not in an intimidating way, with dark hair and a really lazy smile that reached his eyes just enough to make people feel like they were in on a joke with him that no one else got. He was smart, and funny in a really dry way that reminded me of Norm MacDonald (whom I had a strange crush on then and still sort of do, no shame). He shared my love for ’90s alternative bands like Goo Goo Dolls, The Wallflowers, and Vertical Horizon – bands whose peak was just enough in the past for them not to be cool anymore, but just recent enough for people to recognize and consequently side-eye us about.

But he knew how to play their songs on the guitar, which he did for me on the nights he picked me up from my house at midnight to sit by the Halifax River. Between songs, we’d share brownie Frappuccinos and he’d make remarks about how I shouldn’t diet so much because I had a great body (he was right). He’d tell me my about-to-go-off-to-college haircut looked nothing like a mullet (he was wrong). He told me I’d be unhappy pursuing computer science (right again). While we drove around late at night, he’d purposely play songs whose lyrics hinted at something deeper between two friends, or an unhappy relationship getting in the way of something real. I’d pretend not to notice and just smile as I looked out the passenger-side window, watching the palm trees fly by; he liked to drive fast. He’d tell me how great it would be if my boyfriend and I broke up so we could mess around. He was the Trent to my Daria, so I took this guitar-plucking, late-night-tryst, shameless flirting in a way most teenage girls probably would – that something more was there, and fate would step in at some point to tell me what to do.

But the truth is, we never would’ve worked long term. I had big-city dreams, and he didn’t. I had a home life that seemed a lot more awful and unfair than it actually was as, again, most teenagers seem to figure out once they reach true adulthood. His home life was also less than ideal, but in a different way; his parents were divorced, and his upper-middle-class upbringing was a million miles apart from my own more humble one. He was the type of person to mysteriously acquire a police loudspeaker and use it to prank people while we were driving around and had nothing better to do, while I was content with letting the pages of a novel experience the most outlandish shenanigans for me. In our senior year, he won Most Unique; I won Most Dependable. We both had a lot of our own mental demons whose inner-workings, when combined, would’ve eventually imploded and massacred any world we could have created together. And most of all, he didn’t feel the same way about me that I did about him.

Over spring break 2004, I almost left my boyfriend to explore what might have been there with this “What if?” situation, but I chickened out at the last minute because 1. I truly did love my boyfriend, 2. I was scared out of my damn mind, and 3. A dear friend of mine, who is still one of my best friends to this day, talked me out of it. But later, when I finally worked up the courage to tell Henry I thought I was in love with him (something I’m still not proud of to this day, as I was still with the aforementioned boyfriend at the time), he shut down communication completely for a while. He was good at that.

We still talked intermittently over the following year between the time he starting building that wall and the time my boyfriend and I broke up, but I suspect it was only because he felt bad about screening my calls. One of the last times I spoke to him was in 2005; I called (I was the only one who did at that point), and he picked up the phone and greeted me in a groggy voice. I asked if I’d woken him up, which seemed strange considering it was mid-afternoon. He asked me if there was a reason I’d called on that particular day, and when I asked why he thought so, he told me he’d just undergone surgery to have cancer removed. I immediately started crying and telling him I wanted to book a plane ticket (he’d moved up north at that point, though he eventually did move back to Florida) to come up and see him, but he’d already moved on from any life that included me. He had a girlfriend who’d moved up with him, and she had been the one for a while. She took care of him. He eventually married her.

More than 10 years later, I’d be lying if I said I don’t still think about Henry, or that he never pops up in my dreams. I can’t say with a straight face that I’ve never stalked his wife’s Facebook page and smiled when I saw photos of their wedding day and two beautiful children – children I’m not sure whether he knew he’d be able to have, given the type of cancer he’d been diagnosed with – or that I never wonder if I’ll bump into him accidentally when I’m in Daytona. When Vertical Horizon’s “Everything You Want” was an answer at my favorite trivia night a few weeks ago, I thought of him and smiled.

But I can safely and confidently say that if I could go back and change anything, I wouldn’t. Because Henry gave me such an amazing gift: He taught me that letting out your feelings is potentially the most important thing in the world, and that everything happens for a reason – to an extent, at least. Because of Henry, I learned that speaking out now is crucial, because later may never come. Because of Henry, when I met the man of my dreams who gave me that similar, “What if?” feeling, I didn’t let him go. And this time, he actually loved me back. Because of Henry, I married the right person. And I think he did too.

I still never learned to drive stick. But the more I think about it, the more I realize I don’t have to.

(Image via Orion Pictures)

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