21 Funny Long-Form Dating Stories That Are Almost Too Weird to Be True
1. The Nap Date
We didn’t even make it to dinner. She said she had a long day, asked if we could just hang out at her place. I figured we’d talk, maybe watch something. Instead, she handed me a pillow and said, “You take the left side, I’ll take the right.” We napped for two hours. She snored like an old diesel truck but still held my hand mid-dream. We woke up confused and rested. It was the most peaceful first date of my life.
2. The Oversharer
Ten minutes in, she told me about her ex. Twenty minutes in, I knew about her ex’s dog, its bladder problems, and how she missed it more than the ex. She cried when the waiter brought the water because her ex’s dog also loved ice cubes. I nodded politely and ordered mozzarella sticks. She asked if I was emotionally available. I said I was mozzarella-available. We didn’t talk again.
3. The Wrong Apartment
I walked her home and went in for a kiss on the doorstep. She paused, then turned beet red and said, “I don’t live here.” Right on cue, the actual tenant opened the door in a bathrobe holding a cat. We all stood there frozen until I said, “I guess this isn’t your cat either?” She laughed, we ran, and I walked her to the actual apartment. We ended up laughing for the next hour over takeout.
4. The Too-Honest Guy
He looked great, dressed well, and brought flowers. Ten minutes in, he said, “I’m only doing this because my therapist said I need to connect with other humans.” I laughed. He didn’t. He then ranked every woman he dated in the past year out loud, including a column for “smells.” I faked a call from my dog groomer and left.
5. The Dance Floor Disaster
He took me salsa dancing. I warned him I had no rhythm, but he insisted it’d be “natural.” It was naturally horrific. He spun me into another couple, stepped on my foot twice, and ended the night apologizing to the bartender after knocking over a tray of mojitos. We both laughed until our stomachs hurt. I didn’t fall in love, but I did fall — three times.
