Funniest thing someone paid you to do...

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When I was 14, my neighbor Jake slapped a crisp $50 bill on my desk during study hall and whispered urgently, "I need you to be my girlfriend for three hours this Saturday."
My pencil froze mid-equation. I stared at him like he'd just asked me to help him bury a body. "Excuse me?"
Jake was this quiet, nerdy kid who lived next door. Sweet guy with a genuine smile, but about as socially confident as a wet paper towel in a thunderstorm. We'd been neighbors since elementary school, and I knew him as the kid who built elaborate Lego cities and always had grass stains on his knees from lying in his backyard stargazing.
His problem? His ultra-successful older brother Marcus was coming home from college with his new girlfriend, and their parents were throwing this big family barbecue to celebrate his dean's list achievement. Again.
"My brother's been bragging to everyone about how I'll never get a girlfriend," Jake explained, adjusting his thick black-rimmed glasses nervously. "He told my mom last week that I'm going to die alone surrounded by chemistry textbooks. I just need someone to show up, hold my hand maybe, and prove him wrong. Just for one afternoon."
Jake had always been the family underdog - while Marcus starred in varsity sports and student government, Jake spent Friday nights programming or reading science fiction novels.
Fifty bucks for three hours of fake dating? I was desperately saving for a new phone since mine had a cracked screen and a battery that died if you breathed on it wrong. Honestly, it seemed like the easiest money ever.
Jake gave me a briefing session that evening that felt like we were planning an elaborate heist. We sat on his back porch with notebooks and everything. My fake backstory was carefully crafted: we met in chemistry class, I loved reading fantasy novels, and we'd been "dating" for exactly two months.
The day arrived gray and humid. I showed up at exactly 1 PM wearing my best sundress. Jake answered the door looking surprisingly put-together in khakis and a button-down shirt, though I could see the nervous sweat on his forehead.
Jake's backyard was packed with relatives milling around picnic tables laden with potato salad and hamburger patties. And there was Marcus - this tall, confident college sophomore who looked like Jake but with broader shoulders, perfect teeth, and the kind of easy smile that probably made professors give him extra credit.
"Well, well," Marcus said, approaching us with a beer in hand and that trademark smirk. "So you're the mysterious girlfriend Jake's been telling Mom about. Didn't think little Jakey had it in him, to be honest."
That's when I realized this wasn't just about proving a point. Jake was genuinely hurt by years of these casual put-downs disguised as brotherly teasing. I could see it in how his shoulders immediately slumped, how he avoided eye contact and started fidgeting with his shirt hem.
Something protective flared up in my chest. This wasn't just about fifty dollars anymore.
So I did something completely off-script. I grabbed Jake's hand firmly, looked Marcus dead in the eyes with my sweetest smile, and said clearly, "Actually, Jake's the one who's too good for me. He tutored me in chemistry for months before I finally worked up the courage to ask him out."
Jake's face went bright crimson, but I kept going. "He's thoughtful enough to remember that I prefer sci-fi to romance novels, funny enough to make me laugh during pop quizzes, and way smarter than anyone in our grade."
The whole family had turned to listen now. Jake's mom practically melted into a puddle of maternal pride. His dad patted him on the back with genuine approval. And Marcus? He actually looked genuinely impressed for the first time.
For the rest of the barbecue, something magical happened. Jake relaxed completely, his natural personality finally shining through. He started cracking jokes about his robotics team, telling animated stories about the battle bot they'd built for regionals, even teaching his little cousins card tricks he'd learned from YouTube.
I found myself laughing at his stories, genuinely enjoying his company. When had quiet Jake become this entertaining? I wasn't acting anymore - I was having real fun watching him finally get the recognition he deserved.
The barbecue ended as the sun set. Jake walked me home and quietly handed me the fifty-dollar bill. But as I reached for it, he hesitated and said softly, "Hey... would you maybe want to hang out tomorrow? No payment required, just... because it might be fun?"