My Crush’s Setup Backfired / Chapter 1: The Dare That Broke Me
My Crush’s Setup Backfired

My Crush’s Setup Backfired

Author: Grace Davis


Chapter 1: The Dare That Broke Me

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In the dim, neon-lit karaoke room at Riverlight—sticky faux-leather couches, wireless mics squealing with feedback between K-pop and 80s throwbacks—Natalie was leaning in close to my roommate Derek, her eyes shining with mischief as the rest of our group rallied around them, going nuts. Pitchers of beer were sweating rings onto the low table, the air thick with peach soju and bar fries, and the bouncer had slapped 21+ wristbands on us at the door. My jaw flexed as phones went up to film; someone laughed, “This is going on stories.”

“Kiss! Kiss! Kiss!” Different voices layered in from every direction—“Do it!” “Let’s go!”—like the chant was part of the track.

Natalie smirked, a playful curl at the edge of her lips, and just when everyone thought she’d go for it and kiss Derek, she pulled away at the last second. She slid her hand past her wine glass, tapped the stem in a mock toast—lipstick smudge catching the neon—then grabbed the waiting tequila shot instead. “I’ll take the penalty—shot it is,” she said, tilting her head with a dramatic flair that made her gold earrings swing as condensation slid down the glass. She lifted it with her left hand—like she always did—and downed it like a champ, salt and lime. Even though she’d dodged the dare, I caught Derek’s ears burning red—still glowing from the attention, letting out an over-loud laugh and cutting a glance around to see who’d noticed. The crowd whooped and laughed, loving the spectacle, but for me it was like a floodlight flipped on me—deer-in-headlights—and my fingers dug into the sticky couch. I forced a laugh that died fast. Jealousy hit hard, even though it was supposed to be harmless fun.

Natalie. The girl I’d been mooning over since before middle school. It felt like my feelings for her were written across my face in bold marker—everybody knew. She was always the star of every gathering, the kind of girl who turned heads from the moment she walked in: gorgeous, long-legged, quick-witted, and the daughter of a local real estate mogul who owned half the restaurants on our block. Guys lined up for a shot with her, like she was homecoming queen every day of the week—prom committee lead then, Greek-life magnet now. Me? I’d lucked out early—we grew up in the same neighborhood, went to the same schools, even took piano lessons with Mrs. Evans on Saturdays. People envied how close I was to her, but they didn’t get it: I was just another fool hoping for a shot. She’d always known I liked her. I’d put my heart out there so many times I lost count. She didn’t say yes or no—she’d leave me on read, throw me a rain-check, keep me orbiting. After a while, I got smarter and stopped bringing it up. I knew that if I pressed too hard, even our friendship would unravel. Still, whenever she dodged my feelings, she’d toss me just enough hope to keep me hanging on. It’s impossible to just turn off feelings that have been running for years. Seven years, and I was still hopelessly into her—now we were sophomores at Riverside U, and the ache hadn’t gone anywhere. Even now, I watched her earrings swing as she laughed at someone else’s joke. But honestly, she never texted unless she needed to fill a spot for something—today was no different. My dad even made dumb “you two should just get married” jokes at backyard cookouts, which didn’t help.

Her roommate Aubrey was having a birthday, so Natalie messaged me: “Caleb, Riverlight Karaoke, 214 Riverside Ave. My roommate’s birthday—don’t be late.” No emoji, no please—pure command. But I couldn’t say no to her. Pathetic as it was, I came running—again—telling myself it was just a birthday, we were friends, it wasn’t a big deal.

“Natalie, you lost again. Truth or dare?”

“Dare. Always,” she shot back, tapping the table like a card shark laying down an ace, that confident grin saying she was here to win.

“Among the boys here, pick one and give him a kiss—your call how you do it.”

“Aubrey, you’re out to get me, aren’t you?” Natalie laughed, leaning back.

“Hey, we let you slide last round; no ducking out this time!” Aubrey squealed, someone already filming for IG stories while Derek gave an awkward too-loud laugh.

“Fine, you’re the birthday girl—I’ll play along to make you happy.”

There were only three guys in the room: me, Derek, and one of her boyfriend’s buddies. The dare was basically a coin toss—me or Derek. When Natalie’s gaze landed on me, my heart threatened to jump right out of my chest. I wanted her to pick me, but not like this—God, not as a joke in front of everyone. In my head I played both versions: her choosing me and the room exploding with laughter; her choosing him and proving I’d never been first. I dropped my eyes, knuckles whitening on my knees. The crowd’s rowdy shouts rose. When I looked up, Natalie leaned in and kissed Derek—right on the forehead, light and quick, teasing, safe. Just like that, she’d picked a guy she’d barely met over me. It was crystal clear: I’d never been her first choice. I was always the fallback plan. Heat burned behind my eyes and I stood up so fast my chair nearly tipped over.

“I’ve got something to do. I’m heading out,” I blurted, grabbing my jacket, not caring if I looked rude. I had to get out of there—neon buzzing, a half-started 80s hook blaring—pushing through the door just as my phone buzzed in my pocket with an unknown number lighting the screen.

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