People Recount Their Best and Worst First Dates Ever

By Group September 12, 2019

First dates can either be amazing, horrible, or somewhere in-between. We decided to go with the two extremes, and asked people to tell us about their best and worst first dates. Enjoy and stay positive!



Best Dates


Raw fish and good weed

“It started out with sushi and ended with high sex. That’s all I’ll say…”

-CB, St. Louis



Dinner at a diner

“It was super chill, which I appreciated. I don’t like feeling like I have to dress to the nines in order to meet someone I might not even like. He ordered a milkshake and I ordered a hot chocolate. We talked and the conversation flowed easily. Plus, there was amazing people watching.”

-KD, Charlotte, NC



The road trip

“We couldn’t decide what to do, we just had a plan to get out of the city for a day. So this first date kind of evolved into a mini road trip. We drove to another state, went hiking in the woods. It was purely magical. Although, I can see how it would have been TERRIBLE if I didn’t like the person I was with. So I guess it was a risk that paid off.”

-EG, Boston



Worst Dates


The mayo jar

“I was just trying to get to know her and she came over. I had wine, and she got hungry so I offered her healthy snacks. She asked if I had ranch, which I didn’t. So she goes to her car and grabs a fucking jar of mayonnaise – A JAR!! And she starts dunking carrot sticks in the mayo jar and eating them! Truly, it wasn’t all about the mayo jar thing. There were so many other incompatibilities on that date, the mayo jar thing just sealed the deal.”

-CB, St. Louis



The baseball game from hell

“I was talking to a guy online and he said he had tickets for a Yankees game. I thought it was kind of a weird idea for a first date but I went with it anyway. Turned out I was right…NEVER go to a baseball game for a first date!!! It was so long, I had way too many beers, and even though I wanted to leave early it felt too awkward to just leave the game.”

-DM, Brooklyn



Any movie. PERIOD.

“I always regret going to a movie for a first date. It’s dark, you can’t see the person, and you can’t talk. What’s the point?”

-JR, Nashville



Do you have a crazy first date story? Tell us all about it at