From Craigslist to LOLs: My Dating Disaster (and Hilarious Stand-Up Set)
Every comedian needs material, but I didn’t expect mine to come from a Craigslist dating ad. Yes, Craigslist. I know—what was I thinking? Even as I clicked the “reply” button, I could feel my future self shaking her head. But hey, loneliness makes people do questionable things.
The ad was short and sweet: “Looking for love, laughter, and someone who enjoys long walks in Walmart.” Honestly, that felt relatable. I thought, Why not? After a few emails back and forth, we agreed to meet for dinner at a little diner off the highway.
The first red flag appeared before I even made it inside. He showed up wearing Crocs—with socks. Not ironic Crocs. Not farm-chores Crocs. Bright lime green Crocs, paired with white tube socks that had seen better decades. I told myself not to judge. Maybe he had great personality Crocs.
We sat down, and before the waitress could even bring water, he announced, “I don’t eat vegetables. Ever. They’re a government scam.” I blinked. He leaned in and whispered, “Carrots are propaganda.” I tried not to laugh, but a snort escaped. Apparently, that was encouragement, because the conspiracy theories kept coming.
By the time the food arrived, I was halfway convinced this was an undercover improv prank. He ordered chicken tenders and fries, then proceeded to dunk them in his sweet tea. Not ketchup. Not ranch. Sweet tea. He told me it was “his thing,” like he was a Michelin chef pioneering a new cuisine.
As if things couldn’t get worse, halfway through the meal, he pulled out his phone and proudly showed me his YouTube channel: twenty-seven videos of him playing the kazoo to popular theme songs. “I’m gonna blow up any day now,” he said. I nodded politely, all the while plotting my escape route.
The final straw? When the check came, he slid it across the table toward me and said, “You got this, right? Equal rights and all.” I nearly spit my water.
Needless to say, there was no second date. But there was a silver lining: that disaster became comedy gold. A week later, I stood on stage at an open mic, retelling the story. Crocs. Carrot conspiracies. Sweet-tea chicken nuggets. The crowd roared. Every cringe-worthy detail that made me want to crawl under the diner booth became punchline after punchline.
And the best part? Comedy gave me what Craigslist couldn’t: connection. Complete strangers laughed with me, some even nodding like they had their own horror stories of dates gone wrong. One woman shouted, “Mine dipped pizza in Mountain Dew!” and suddenly, we were all bonded by the absurdity of love gone wrong.
That night I realized something important. Dating disasters may break your heart, but they make your audience howl. They remind you that the worst moments—Crocs included—can turn into the best material.
So while my Craigslist romance was a bust, my stand-up set was a win. And if you ever see a guy dipping chicken in sweet tea? Run. Or better yet, take notes—you’re going to need them for your next comedy routine.
