When Harry Met Sally might be the greatest romantic comedy of all time—not just because it’s a beautiful love story, but because it so perfectly captures the mishaps and horrors that often precede a happily-ever-after. Consider the scene in which Harry and Sally, just friends at this point, engage in a little game of one-upmanship that any veteran of modern-day matchmaking will recognize.
“How much worse can it get than finishing dinner, having him reach over, pull a hair out of my head, and start flossing with it at the table?” Sally asks.
“We’re talking dream date compared to my horror,” Harry replies, archly, before launching into his own tale of attempted romance gone awry.
This is to be expected. The thing about dating horror stories is that they’re an invitation to share your own—tales of awkward fumbles and cringing humiliations and kisses intended for someone’s lips that somehow instead ended up in their ear canal.
I have a little cache of these from my single days, no less potent for being nearly two decades old. Some of them are objectively funny, like the guy who glanced at my legs, grimaced, and told me I had “borderline cankles.” Others, not so much—like the boyfriend who invited me to visit him at college, brought me to his dorm room, had sex with me, and dumped me, all in the span of roughly seven minutes. I hadn’t even put my clothes back on.
I drove the 150 miles back to my own campus, sobbing hysterically—only to discover an email from my now-ex waiting in my inbox. My heart leaped as I opened it: Was it an apology? A groveling plea to come back?
“Hey,” it said. “FYI, you left your underwear here.”
