Top 15 Strangest Things I’ve Done (or Have Been Done to Me) on a First Date

Pictures of the Autostraddle senior editor team are collaged in colors of cobalt and orange with the words "Happy Birthday Autostraddle" and the number 15 strewed all over for Autostraddle's 15th birthday

Autostraddle is turning 15 this week! To celebrate, we’re publishing chaotic and gay Top 15 Lists all week long.


As the cohost of Autostraddle podcast, Wait, Is This a Date?, I’ve been on my fair share of first dates. And my fair share of maybe dates. And one night stands that felt like dates. And friend hangouts I found out later were dates.

Some of these dates involved going to a bar and getting a drink and doing the usual small talk, but some of these dates were STORIES. I love when dates are stories. I’d rather a first date be bad but a story than be fine and boring. Give me drama! Give me intrigue!

So, in honor of Autostraddle’s birthday, I’ve decided to collect the 15 strangest things I’ve done (or have been done to me) on a first date.

Strange doesn’t always mean truly wild. It can often mean strange because it’s so nerdy or random why would anyone do that on a first date. That’s right! I’m getting vulnerable here! But what I promise is each of these sentences contains a story. Some of these stories can be found in the archive of this very website. Some of these stories remain unshared beyond my friends. But shoutout to these 15 people for not being boring — or, at least, being boring in a funny way.

15. Sucked orange slices out of her hands

14. Ended early because her ex-girlfriend was in crisis*

*she identifies as straight now

13. Spent two hours on public transit to meet a couple staying at the JFK airport

12. Watched hours of old episodes of NeXt and ElimiDate

11. Met up at her apartment at 7am to eat pancakes*

*it was her birthday

10. Read several chapters of Anna Karenina out loud to her, by her request

9. Got rejected because I didn’t pay enough attention to someone’s dog

8. Got rejected because I paid too much attention to someone’s dog

7. Went to The Taylor Swift Experience at The Grammy Museum*

*this is strange if you know how much I hate Taylor Swift

6. Read love letters her roommate had written her while we mocked him*

*they’re married now

5. Traveled three hours upstate together on the Metro North, walked around for a few hours, then traveled three hours back down to the city

4. Looked at pictures of trans surgery scars*

*she was cis… and I’m sure still is

3. Visited The Parsonage of Aimee Semple McPherson

2. Had sex while watching Myra Breckinridge*

*ideal t4t first date tbh

1. Started to have a threesome with my date and a Michael Jackson impersonator while the Michael Jackson impersonator waited for a coke connect, before we both realized we were just doing it for the other person, started singing along to Avril Lavigne to stop the kissing, and then ran away to make out sans Michael Jackson impersonator


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Drew Burnett Gregory

Drew is a Brooklyn-based writer, filmmaker, and theatremaker. She is a Senior Editor at Autostraddle with a focus in film and television, sex and dating, and politics. Her writing can also be found at Bright Wall/Dark Room, Cosmopolitan UK, Refinery29, Into, them, and Knock LA. She was a 2022 Outfest Screenwriting Lab Notable Writer and a 2023 Lambda Literary Screenwriting Fellow. She is currently working on a million film and TV projects mostly about queer trans women. Find her on Twitter and Instagram.

Drew Burnett has written 515 articles for us.

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