Chapter 1
I Couldn’t Kiss Worth a Damn
Crestview High, 1986.
If you were cool, you had a jean jacket, a Walkman, and knew how to lean against a locker like a movie extra in The Breakfast Club. I had none of those things. I had a lunchbox with a Van Halen sticker, an unfortunate bowl cut, and the emotional depth of a Hall & Oates record.
All I wanted was to kiss Hailey Dupree before Halloween.
Hailey was everything. She looked like she belonged in a Pepsi commercial: teased hair, hoop earrings, and a jean skirt that defied physics. She always smelled like strawberry shampoo and lip gloss. We had exchanged approximately 2.5 conversations, including the time she asked to borrow my pencil in homeroom and never returned it. I didn’t care. I still have dreams about that mechanical pencil.
At one point, I convinced myself she could read minds — not because she looked psychic, but because she once laughed right when I thought something funny. Granted, I had also just sneezed into my elbow, and she may have been laughing at that, but the timing was uncanny. I once wrote ‘Hailey Dupree’ in Elvish in my notebook, because I thought maybe she secretly liked The Hobbit. She didn’t. But I kept writing it, anyway. I even started noticing empty Bonne Bell lip gloss tubes in the hallway trash and wondered — just maybe — if one had been hers. That’s how far gone I was.
And look — I know it sounds creepy. But it wasn’t about kissing, not really. It was about connections. I dreamed of someone looking at me as if I mattered. My obsession wasn’t with Hailey herself, but with the idea of having a good friend. Someone who’d sit next to me in the lunchroom without irony. Someone who might actually laugh at my jokes on purpose. That kind of magic. That kind of hope.
Lucia, of course, gave me endless grief about it. She’d catch me zoning out in math class and mutter, “There he goes again — starring in a one-man romantic fantasy about a girl who doesn’t even know his last name.” She once threatened to host an intervention with a whiteboard diagram titled ‘Reilly’s Hailey Delusion Spiral’. I knew she was joking. Mostly. But she wasn’t wrong.
However, the truth was that kissing Hailey wasn’t really the goal. I wanted to belong. To slip through the crowd and land in that weird space where you’re not the butt of the joke. Where people see you, maybe even like what they see.
“You need help,” says Lucia Morales, my best friend since second grade and easily the most intimidating girl at Crestview. She was gorgeous in an effortless, roll-out-of-bed-and-still-look-like-Lisa Lisa kind of way. She had that East Coast fire — Puerto Rican and Dominican, fluent in sarcasm and side-eye. Guys hit on her constantly: in the halls, at the arcade, even once in the middle of a traffic jam. She shut them down with the look that says, ‘Try again in another life.’ Rumors flew that she was into girls or secretly dating someone older. The truth? She just didn’t have time for people who didn’t get her.
“It’s a basic plan,” I tell her, as we stand in line at the video store thumbing through VHS covers that smell faintly of plastic and mildew. The neon lights flickered overhead, as if they were deciding whether to give up. “Find Hailey at Greg Talbot’s party. Make conversation. Build chemistry. Go in for the kiss.”
Lucia stared at me like I’d just said I wanted to wrestle a tiger.
“That’s not a plan, Reilly. That’s a chemical spill waiting to happen.”
“You think she’ll say no?”
“I think,” she says, handing me a copy of Ferris Bueller’s Day Off, “you’re going to panic, say something weird about her earrings, and end up kissing her shoulder.”
I gave her a look. She gave me popcorn-flavored bubble gum.
Greg Talbot’s party was a glorious mess of Aqua Net, neon legwarmers, and parents who decided the best way to supervise teenagers was to hide in the basement and hoped nobody died. The living room smelled like Doritos, sweat, and desperation. A Lite-Brite lamp glowed in the corner like it had secrets. Music pulsed through the walls — Bon Jovi, loud and dramatic, like it had something to prove. I arrived with Lucia, who immediately peeled off to “get away from the swarm of testosterone” buzzing around her.
I spotted Hailey near the stereo, flipping through cassettes. My stomach flipped, and my palms started to sweat like they were preparing for a job interview.
This is your moment, I told myself. Be cool. Be bold. Be… a person who knows where their mouth goes.
I took a breath. I had rehearsed this in the mirror like a lunatic. Now I couldn’t remember if my mouth was supposed to move first or if that would scare her.
“Hey,” I say, casually leaning on the wall. It was not a wall. A foldable ping-pong table: That’s what it was. It collapsed instantly, taking me with it in a screech of metal legs and plastic clatter.
Hailey looked down at me. “Reilly, right?”
“Yep,” I say from the floor. “Just testing gravity. Still works.”
Somehow, we talked. Maybe she liked disasters. We stood near the punch bowl, which tasted like flat cherry cola and vague regrets. We talked about Mr. Laskey’s inability to operate the overhead projector and how lame the Homecoming theme was (“Dreams in Denim”, seriously?).
Then, without warning, we were outside on the trampoline. I did not know how we ended up there, but suddenly the stars felt too close, and the grass smelled like wet sneakers and teenage nerves.
She was looking at me.
This is it, I thought. Do the thing.
I leaned in.
She leaned in.
And then I kissed her.
Well. I attempted.
It was more of a facial ambush. My upper lip made contact with the bridge of her nose. I forgot to close my eyes. Her hair got in my mouth — it tasted like aerosol and sugar. At one point, I think I sneezed. It was like trying to kiss a moving target while being mildly electrocuted.
For a moment, I thought it might still work until I opened my eyes and saw hers, confused, blinking.
She pulled back. “Oh.”
I stared at her. “Yeah. I’m kind of new at this.”
She smiled politely, like she wasn’t sure what else to say. “You’ve got time.”
I nodded, trying not to cry or glance at the patio, where Lucia watched me with a look of equal parts amusement and mild horror.
Later, she found me sitting on the curb. The air smelled like warm asphalt and burnt charcoal from an abandoned grill.
“Well?” she says, handing me a can of New Coke that hisses softly when opened.
“I kissed her. Sort of.”
“Define ‘sort of’.”
“More like… made physical contact with her face in a way that technically involved lips.”
Lucia shook her head and cracked the soda. “You’re hopeless.”
“I prefer ‘romantically unconventional.'”
We sat in silence, the sound of Take On Me leaking out of the house behind us, muffled but full of synth and longing.
Then she asks, “Why her?”
“What do you mean?”
“Hailey. I mean, she’s nice, sure — and you’re adorable in a lost-puppy sort of way — but she barely knows you exist.”
I shrugged. “I don’t know. She’s pretty. And popular. And I thought… if I kissed someone like her, maybe I’d feel more normal. Less… Reilly.”
Lucia gave me a long look. “Okay, number one, there’s nothing wrong with being Reilly. Second, you don’t need to kiss someone to prove you’re not weird. And third — and I say this with love — you suck at kissing.” She grinned. “And that thing with your lips? You looked like a confused frog.”
“That’s fair,” I mutter.
She paused for a moment, eyes softer now. “You know, I get it. That feeling like you’re always standing outside of something. Like maybe if you just do the right thing, wear the right jacket, say the right line… maybe you get to be part of it.”
“Exactly.”
“But Reilly — trying to be someone else is like wearing jeans two sizes too tight. You might fit, but it hurts to breathe.”
She hesitated, then adds more quietly, “You think I walk around like I own the place because I’m fearless? Nah. That’s just armor, McGee.”
“You’re weird. Own it.”
She smiles. Not the snarky one. The real one. Then she reached out and brushed her fingers against mine, just a soft touch, but it felt like electricity — the good kind.
“Eres más valiente de lo que piensas, Reilly,” she whispers.
I blinked. “What does that mean?”
She smiles again, this time with a hint of mischief. “It means you’re braver than you think. Even if you kiss like a confused goldfish.”
I laughed — really laughed — and for the first time all night; I didn’t feel like I had to be anyone else.
She said nothing more. She didn’t have to. That soft brush of her hand said more than any pity-kiss ever could.
It hit me — the kiss wasn’t the milestone. This was. Sitting next to someone who knew me at my weirdest and stayed, anyway.
“Okay. Just… next time, aim lower. Like actual lips. Open your eyes so you can see what you are doing.”
I couldn’t kiss worth a damn. But for a minute, I felt free. Not because it went well. But because I did something that scared me. Because I put myself out there. Because, in 1986, with braces and a bowl cut, I kissed a girl who smelled like strawberry shampoo and didn’t laugh in my face.
It didn’t make me cool. It didn’t make me normal. But it made me brave. And for a weird kid with braces and a dream, that’s got to count for something.