Playful Escapades

I thought returning my best friend’s compliments was harmless fun. Then she told me to stop—and objected when I did.

I mentioned buying an Xbox for GTA 6. My girlfriend heard a plan to replace our evening calls with a virtual romance.

At 52, I tried swiping right first and reading profiles after matching. The men using the same method had some objections.

He invites me to gigs, cuddles with me, and walks me home. I still start most of our texts—and my attempt at a hint may have backfired.

Near the end of a fifteen-hour flight, I offered a stranger some unsolicited dating encouragement. His reply was brief.

We’d texted for a week, and I thought our coffee date was going well. Then she told me I was too normal and too chill for her.

I can talk to women just fine once we get started. At Halloween, a costume did the part I usually get stuck on.

At 27, I’d never asked a woman out. I tried the simplest opening—and picked someone who was about to leave in an ambulance.

I barely correct coworkers who mispronounce my name. Then I gave a promising date a ten-minute lesson and made two wrong vowels my final straw.

A first date was going nowhere when a woman across the bar caught my eye. I left with one ambiguous glance and one very clear unmatch.

At 45, I accepted a dinner invitation after a great conversation. Then his graduation dates suggested a much bigger age gap than I expected.

I stopped trying to impress dates over expensive dinners and suggested Sunday brunch. That date kept finding reasons to continue.