A relaxed date changed how he felt about a woman he hadn’t expected to like—but her being five inches taller still gives him pause.
Playful Escapades
Funny first dates, awkward flirting, and romantic plans that don’t quite go as expected. Stories with dry wit, surprising encounters, and plenty of second-guessing.
The $1,500 Dinner That Suddenly Felt Like Too Much
A quick drink in her city left me unsure about the $1,500 private birthday dinner I’d planned—and whether to keep the reservation.
The Poodle Got a Treat; I Got a Friday Invitation
I bought a bag of freeze-dried beef-liver treats before my date because her poodle, Katie, was coming along. The plan was simple: save them for the end of our walk and let Katie have her little moment. I was, after all, hoping to make a good impression on both members…
A Lovely First Date, Then an Invitation Home
A good first date has a particular kind of momentum. The conversation flows, the narrator describes good chemistry, and before dessert arrives there’s already a plan for a second date. Even the brief kiss beside the cars fits neatly into the evening’s hopeful little storyline. Then, about five minutes after…
He Asked About Her Skincare Routine. Then He Asked Again.
They had agreed the coffee date would be brief: a preliminary meeting, with dinner that weekend to follow if they both wanted it. It was a sensible arrangement. Nobody had to commit to a whole evening before finding out whether conversation could survive a drink. Conversation, as it happened, was…
My Gym Crush and I Are Very Serious About Nodding
For about six months, she had been seeing a man at the gym. Seeing him was going very well. Speaking to him remained a separate project. They nodded. They waved. There was recognition, continuity, a certain reliability. In another setting, this might have counted as a working relationship. She was…
My Post-Breakup Apartment Became the Rejected Housewives Suite
I moved into a one-bedroom apartment after my breakup, expecting solitude. Within weeks, it had become the Rejected Housewives Suite. Several residents…
I Agreed to Move In Before I’d Finished Breakfast
“We should move in together,” Matt said over breakfast.
Your Date Has Heard Enough About Burning Man
Ten minutes into dinner, I knew that Ryan had attended Burning Man. Twenty minutes in, I knew he had been transformed by it. By dessert, I was…
I Mistook My Ex’s Bad Hair Day for Cosmic Justice
Two years after my ex cheated with a colleague, I saw him while out for a walk. His once-impressive curls had thinned. For one extremely undignified…
The First Red Flag Was Crocs. The Second Was My Reasoning.
A man once refused to kiss me goodnight because I was holding a croissant. “I don’t believe in breakfast,” he said, with the confidence of somebody…
Bob Investigates Whether Being Selective Makes Him Attractive
Bob wondered whether being selective made him attractive. It was a question with obvious practical limitations: if he asked a woman and she said no, he…