I was 23 and thought she was around my age. Making my interest clear revealed the one question neither of us had asked.
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.
Does My Female Friend Make Me Look Taken?
I go clubbing with a good friend. Now I wonder whether women see us together and assume my flirting comes with a girlfriend attached.
She Invited Me to Halloween After One Tinder Date. I Have a Strategy.
She invited me to her Halloween party after one good date. Now I’m overthinking the arrival time, what to bring and how much to talk.
We Had a Great First Date. Now Do I Interrupt Her Night Out?
After a wonderful first date and a long-awaited kiss, I see her at our local bar with a friend. Our next date is set. Tonight is less clear.
Our Knees Kept Touching, but Was a Phone Number Too Much?
A game night brought easy chemistry and touching knees. Giving him my number somehow felt like the bigger move.
I Said Yes to Every Date Idea—Until He Asked What I Actually Liked
I agreed to a horror movie even though they give me nightmares. After four dates, he had started to notice how little I ever chose.
My Boyfriend Showers Without Soap—and I Only Just Found Out
A first shower at my boyfriend’s place revealed a routine I hadn’t expected—and left me facing a very awkward conversation.
My Best Friend Kissed Me in Front of the Guy Who Wanted Her
He asked me to help him get with my best friend. She turned him down, kissed me, and invited me home. The next morning, he blamed me.
He Said “I Love You”—Then Got Shy When I Brought It Up
A month into dating, my boyfriend said he loved me. I smiled—and my later attempt to respond left us both a little awkward.
I Finally Kissed Her While We Waited for Her Uber
The conversation was easy. Reading the signals was harder. Then we kissed outside while waiting for her ride home.
I Asked If He Wanted to Watch Me With Another Man
I thought a fantasy about another man would turn my boyfriend on. Instead, he pulled away—and I can barely explain why I said it.
She Said We Were Friends. Then Came the Pumpkin Patch.
After she said she wanted to stay friends, a pumpkin-patch outing, haunted-house nerves and a full-arm hug left me unsure what to believe.