IT HAPPENED TO ME: I Dated My Childhood Sweetheart and It Was a Disaster

Nothing in life is ever quite as neat as you would like it to be.
Publish date:
July 2, 2015
Dating, teenagers, IHTM, childhood crushes, high-school sweethearts, The 90's

To get into the right mood for this story, send your mind back to the Roaring ’90s.

Pre-9/11 America: Nick Carter’s hair, MmmBop, scrunchies, cucumber melon body spray. I go to an inner-city elementary school with depressing uniforms and own, not a Tamagotchi, but one of those fake Tamagotchis that just makes noises that you can get in Happy Meals. I think it’s the same thing, so I don’t care.

The scene is set. Settle into your seats. Submitted for the approval of the Midnight Society, this is “The Tale of the Boomerang Boyfriend.”

I was a pretty boy-crazy little kid. I blame this on repeated viewings of Baz Luhrmann’s Strictly Ballroom during my formative years.

I had a type: my friends’ big brothers, especially if they rode BMX bikes. One friend’s older brother shattered his Eminem CD (my mother disapproved heartily of Eminem) and left the shards on our front porch as a demonstration of his devotion. I can’t remember whether that selfless gesture won my mom over or not. It was never explained to her, so it probably just seemed Blair Witch-y.

But in fourth grade, I found The One. His name was Floyd Bleekman (no it wasn’t, but his real name was even worse), and he was a fellow student at my slightly bizarre German immersion elementary school. I remember him as hunky in an angular way. My mom remembers this:

“He had those big circles under his eyes. And a sister. He was on the 5th-grade yearbook team.”

That’s the kind of characterization you can only get from a parent.

Floyd was my first kiss. A circle of kids formed around us at recess under the shade of a pear tree, trying to get us to smush faces (the teachers were probably too busy being German to notice). He seemed to be chickening out, so I turned around to go inside, but then he ran up behind me and surprised me with a kiss on the cheek.

We got one of those rising “ooooOOOOHHHHs” from everyone that meant someone had done something outrageous. Did everyone else have that sound punctuating their childhoods, too? Where did we all learn to make that sound?

It was a wild ride. I would go down the tube slide, he would come up the tube slide, we would peck, then both rush away. One day, he put a Power Ranger toy on the balance beam between where we were sitting, then knocked it off violently to show that he wasn’t going to let ANYTHING come between us, not even the Blue Ranger.

I “broke up” with him because my friends thought he was weird. (I was ten.) He seemed to take it hard, according to my mom, but I was too busy playing Spice Girls to think about it for too long. Fade to black.

Fast-forward 7 years. Incubus, real cell phones, Harry Potter, Priuses.

I’m a junior in high school. My family heads to an outdoor dance festival. I’m pushing my way through a crowd to try and get on the outside of a funnel cake when I hear someone yelling my name. My mom and I both look around, confused, and see a blonde Adonis striding across the street to us, obviously ecstatic to see me. I had no idea who he was, but I definitely wanted to know.

After a solid couple of minutes, my brain finally assembled his features and realized that it was Floyd, all grown up into a WASP-y football player. He was helping his dad sell barbeque at the Rotary Club tent, and just happened to recognize me walking by. It was the most wholesome meet-cute possible. Is it still a meet-cute if you haven’t seen the person since they were shorter than a barstool?

To my amazement, he seemed to have been carrying a torch for me since I broke his heart on that woodchip-covered playground. He abandoned his post at the BBQ booth and accompanied my family around the festival, eventually sliding his hand into mine. Moving a little quick, sure, but I was not about to object. His shoulders were like THIS (wide arm gesture).

Yes, I thought as he nestled his man-smelling head into the crook of my shoulder. YES. This is what my life is supposed to be like. I’m supposed to date cute boys and ride in fast cars and have adventures. It didn’t matter that he wasn’t really my type--up until then I was mostly dating Ichabod Crane-looking guys who loved Belle & Sebastian and the indoors—my horizons needed some broadening.

I also wasn’t immune to a good origin story. We’d chased each other on the playground, and now we’d found each other again! It was sweet enough to give you a cavity.

He drove a simply unbelievably beautiful car, a classic baby blue convertible that rattled terribly any time it went above 45. I hadn’t understood the “he has a cool car” attraction until I saw that car, and deeply desired to steam up its windows at Lookout Point.

Kissing him was like getting hit in the face with a splintery two-by-four, but what seventeen-year-old anywhere is good at kissing? Don’t say you were, you weren’t. He made up for sandpapery smooches by being a human golden retriever; excited, playful, eager to please.

Over time, there was an accumulation of little weirdnesses. He didn’t know how to pump gas. He was physically affectionate in public in a way that felt kind of intense, and he never introduced me to any of his friends. But these were all things that could be lumped under the “teenagers are learning how to not be weird” column. Really, he was a perfectly normal guy, probably the first and last perfectly normal guy I would ever date.

Then, the hammer fell. I hadn’t heard from him in about a week, which I took with mild regrets to be the natural summer fling fadeout, when we got a phone call from his mother.

My mom picked up the phone, so I only heard one half of the conversation.

“Oh, hi! Yes, this is Maddie’s mom.”

“Oh, that’s strange. No, we haven’t seen him.”

“No, he hasn’t come by. I don’t think Maddie’s heard from him.”

She turned around and looked at me, one hand over the phone. “Have you heard from Floyd?”

“No, not for a week,” I said, surprised.

“No, she hasn’t heard from him. We’ll let you know if he calls or comes by.”

“Good luck!”

My mom turned to me. “Floyd has been missing for a week.”

“Missing?” I goggled at her.

My mom elaborated: “Sounds like he had a big fight with his parents, took off driving, and they haven’t seen or heard from him since.”

I don’t think I ever expected him to come back. I liked to imagine he’d taken off for points West, to find America or himself or both; he’d be living on the road, a teenaged runaway scrawling his torn-up feelings in gas station notebooks, jumping from town to town looking for work, until he settled in San Francisco and got happily weird in his middle age.

But instead, after he’d been missing for two weeks, I got a phone call late at night. It was Floyd.

I went into my room and closed the door.


He acted like he hadn’t been missing for a fortnight. It was the same as any other phone conversation; he was just checking in on how I was doing, seeing whether I wanted to go out sometime this week. I had to prompt him:

“So, where have you been?”

“Oh, the YMCA.”


“Doing what?”

“Playing video games. Also, I shaved my head and joined the National Guard.”


“I had a fight with my parents. So I decided to leave and cool off. Then I ran out of gas money, so I had to come back.”

Those are literally all the details I was able to get out of him. He never opened up to me about what the fight was about or why he decided the National Guard was right for him.

He asked one question:

“So, do you want to make this official?”

I hemmed and hawed. I think I said something noncommittal, but not discouraging. My heart hurt, because I knew I didn’t like him That Way. I didn’t love him, and I wasn’t the right person to help him work through this.

I don’t remember a breakup, but he’s not currently my boyfriend, so something happened. I think I saw him once after the phone call, because I remember his shaved head.

He was like Samson, standing on my porch, shorn and plain-faced. The shine had rubbed off, and I saw him not as The Romantic Story any more, but as an unpredictable and strange presence, something that I didn’t have the tools to understand yet.

Nothing in life is ever quite as neat as you would like it to be. Instead of having a lovely summer together to atone for breaking his tiny heart in the past, I ended up colliding with a difficult situation that scared me and pulled a few of the floorboards out of the world I’d constructed.

After all, that’s the difference between being ten and being seventeen. When you’re ten, you don’t have a world built. Anything up to and including Lord of the Flies-type situations could potentially happen; you’d be relatively prepared to adjust since you’re still gathering data.

But when you’re a teenager, you think you’re on a course. You’ve scientific-methoded that shit and now you know how the world works and how things should behave. So when your perfectly normal boyfriend up and runs away, or when your foolproof kickflip move ends up putting you in traction, or you watch a movie with your mom and it suddenly features full-frontal nudity (thank you, The English Patient), everything gets bigger and stranger and weirder in a way that crushes your toothpick castle of a life.

Anyway. Tell me about the boys you held hands with when you were eight. I want to hear all about ’em. My hypothesis: you always remember the first and last name of the first person you ever had a crush on. (Billy Blakely.)