How do I know it's love? Because I've already thrown up twice, and I haven't even asked him out yet. Although my friends could've done without that information, they agree that my anxiety-induced stomach issues provide the perfect excuse to skip school and ask out my first boy ever. Who could focus on imaginary numbers or the Teapot Dome Scandal on a day like this? The signs that I should finally make my move are everywhere: the typical gray soup of overcast skies has finally broken apart over the Chicago skyline, giving way to a hopeful Tiffany blue. It's the first warm day we've had in half a year, which is perfect for my current mission because I can slip into my favorite black tank top that makes it look like I have ripped arms (twist: I don't!). I don't feel guilty skipping. I've already finished most of my finals, junior year is basically over, and half the seniors won't even be present today. Like Andy McDermott. I've been circling Andy all through May with the steely-eyed focus of a shark circling a drowning sailor. He'd been dating this girl in my pottery class for almost a year, but she cheated on him during spring break, they broke up, and then Andy started showing up at our school's LGBTQ+ club meetings. As secretary of the club, the only meeting minutes I recorded that day were OMIGAWD ANDY IS HERE. Hannah, my best friend (and best spy), managed to learn that Andy would be ditching class to go to Grant Park to record TikToks for his band. So that's where I'm headed, as fast as my penny board will take me. The miniature hot-pink skateboard bucks under the weight of my overstuffed satchel, but I easily correct my balance. I am, after all, a little toothpick boy who is seventeen but looks twelve. Spring wind whips against my face as I glide across the rust-colored bridge between my home on the Gold Coast and the Loop downtown. When I reach the lake, I realize the entire city has chosen to play hooky: sailboat owners, bicyclists, joggers, picnickers--each of us desperate to take advantage of the first hint of warmth since October. Yet the soothing wind does nothing to quiet the acid bubbling in my stomach. Today is the day Micah Summers asks out his first boy, win or lose. It better not be lose! When I finally stop my board outside of a stone barrier leading into Grant Park, a stroke of luck finds me: Andy McDermott is already here. And he's alone. It's unfathomably rare to find Andy without his circle of intimidating friends. Yet here he is without them, in line at a street-side hot dog cart. Andy is a boy straight out of a fairy tale--but, like, the vaguely punk kind from Descendants. He has curly dark hair dyed aquamarine at the tips, a smattering of freckles over his lightly tanned cheeks, a stud earring, a flannel shirt tied around his waist, and silver rings on every finger. Ideal retro-music-video vibes. Breathing steadily, I lick moisture back into my lips, clip my board to the back of my satchel, and join Andy in line. He doesn't see me yet. My heart won't settle. The hot dog vendor--a boisterous older white woman decked out in Chicago Bulls merch--waves Andy forward to take his order. How am I supposed to start a conversation? Once I manage that, how do I ask him out in a way that's casual enough to not be off-putting, yet direct enough to avoid our date becoming a passionless friend hangout? In real life, boys aren't fairy-tale princes; they're terrifying, unknowable creatures who hail from the woods of mystery. No time to breathe. I leap to my phone for backup and text Hannah: Emergency! McDermott is in line ahead of me getting hot dogs. What do I do? Her reply comes swiftly: Ask him out! I nearly strangle my phone. Since seventh grade, Hannah has dated one pristine, popular boy after another--and she's always the one who gets asked out first--so I don't know why I think her advice will ever be applicable to me, a gay boy who hasn't even reached a middle schooler's dating level yet. Thank you, Hannah, but how? I reply. Just ask him if he wants to eat hot dogs together. But, like, make it SOUND like "hot dog" is code for something else. You're making jokes while I drown! Offer to buy his lunch! At last, a concrete, actionable first step! Hannah is the queen. "--run it through the garden," Andy tells the hot dog vendor in his coarse, husky voice. "That'll be four fifty," the vendor says. I lunge forward, credit card outstretched, before Andy finishes hunting for his wallet. "It'sonme," I blurt in a single, mishmashed syllable. Andy staggers backward, shock etched across his scruffy face. Oh no. I moved too quickly. "Sorry!" I raise my arms in surrender for some unknowable reason. "It's, um, on me?" Andy flutters long lashes, and his startled expression softens into a crafty smile. That's nice. Breath returns to my chest. "Oh, hey," he says. "Micah? From the school club thing, right?" He recognizes me! "Yes, uh . . ." I say, handing the vendor my card. My gaze leaps around wildly, landing on anything but Andy. The plan is breaking apart fast. To Andy, this twerpy little white kid he barely knows just jumped out of nowhere and isn't explaining why. "Are you getting a dog, too, hon, or just buying his?" the woman asks. The sidewalk is swirling. No way I could eat anything. "Just his," I mumble. "Well, thanks," Andy says, his friendly tone powerless to relax me. With ungodly effort, I meet his eyes--dark brown and flecked with gold. He's smiling. It's too much attention. My stomach squeezes. Smile, Micah. I obey. Too much teeth! I close my lips. Now you look queasy. I am queasy! Andy's smile begins to fade. You're losing him! "I don't know what you're doing tonight," I blurt. Andy's pierced eyebrow rises. "You . . . don't know what I'm doing tonight?" The sentence was supposed to be I don't know what you're doing tonight, but if you're free, do you want to go to a movie/dinner/whatever. But of course, I chickened out on the important part, so I sound like a creep! "Here's your card, sweetie," the vendor says before handing Andy a tinfoil-wrapped hot dog and bag of SunChips. A woman behind me nudges her children ahead to order, and Andy and I shuffle out of line together. Literally what am I doing? Do I just follow him around all day like some sad ghost? "I mean, if you aren't busy tonight . . . uh . . ." I stammer. Mercifully, Andy knows where I'm going with this. Wincing slightly, he leans closer. "Hey, Micah . . . I'm super flattered, but--" "No worries!" I gasp. "Happy graduation, happy hot dog, bye!" I sprint in the opposite direction with the intensity of a gazelle about to become a jaguar's lunch. I don't slow down until the toxic pool of acid inside me disappears. My heart shrivels inside my chest. Once again, I couldn't do it. Excerpted from The 99 Boyfriends of Micah Summers by Adam Sass All rights reserved by the original copyright owners. Excerpts are provided for display purposes only and may not be reproduced, reprinted or distributed without the written permission of the publisher.