25 Questions to Make Conversation with on a First Date

We’re revisiting this classic Autostraddle piece on queer dating as we get back to dating basics in partnership with HER’s Queer Dating 101, a series of live edutainment events that brings in concrete how-tos, insights, experts and some of your favorite Autostraddle personalities to help you find love (or whatever you’re looking for) in the time of corona. Check out the event on Nailing the First Date, complete with a live first date followed by a loving critique, TONIGHT 1/19 at 6pm PT | 9pm ET!


It can be tough to figure out conversation for the first date — something in between the first ten minutes of establishing where you both work/how totally fine this small-plates place is and delving into all your childhood trauma. A relatable icon for adult dating is Real Women Have Curves‘ Ana García bringing index cards of conversation topics to her first date. To that end, here are X open-ended yet casual, chill questions to get to know your date better without it feeling like a job interview or summer camp icebreaker.

1. Is your job now what you imagined doing when you were a kid? What was?
2. What’s the farthest trip from home you’ve made?
3. How did you meet your best friend?
4. What’s your comfort show/book/album?
5. How did you get into doing [hobby]?
6. What superpower would you most like to have?
7. What absurd thing did you believe was true about how the world worked as a kid?
8. Do you have any superstitions?
9. What’s your favorite thing to shop for?
10. Do you have a guilty pleasure TV show or movie?
11. What’s your favorite thing about where you work/live?
12. What’s your karaoke song?
13. What were the urban myths where you grew up?
14. What’s your favorite holiday to celebrate?
15. Who in your life could you put up with being trapped on a desert island indefinitely?
16. Do you believe in ghosts?
17. What TV character do you most relate to?
18. What would your dream house look like?
19. What did you grow up thinking was universal because your family did it, and then realized later it wasn’t?
20. Where have you always wanted to travel to?
21. What ending to a TV show did you hate?
22. What was your clique in high school?
23. Were you a group projects person or do you hate them?
24. Do you believe in astrology? (Lol)
25. What’s the best sandwich you’ve ever eaten?


What questions do you like best for getting to know new people? (Also would love to hear your answers! Especially to 8 and 16.)


Want to learn more? Register for Nailing the First Date tonight, 1/19/2021 at 6pm PT | 9pm ET!


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Rachel is Autostraddle's Managing Editor and the editor who presides over news & politics coverage. Originally from Boston, MA, Rachel now lives in the Midwest. Topics dear to her heart include bisexuality, The X-Files and tacos. Her favorite Ciara video is probably "Ride," but if you're only going to watch one, she recommends "Like A Boy." You can follow her on twitter and instagram.

Rachel has written 1136 articles for us.

31 Comments

  1. I thought I’d be making art, traveling, and playing music. Now I’m transplanting organs in Utah. Life goes in strange directions. How the hell did you end up here?

    • KW

      No one that will be getting a second date with me

  2. I definitely believe in ghosts. The office I am currently sitting in is totally haunted! The ghost will only make its presents known when you are alone in the building.

      • It will turn on and off the lights, to the point where if you ask nicely it will turn the lights on. It also sounds like someone is walking up the stairs and then down the hallway.

  3. I like to pretend I’m not superstitious but I’m actually incapable of discussing bad things hypothetically happening without immediately mumbling in Yiddish about how I don’t mean to tempt the evil eye.

    • The best sandwich I ate was a tuna melt which I had in Lesbos in 2002. I can’t remember why it was so great except that it contained mushrooms* but I remember thinking it was the best sandwich I’d ever had and I’ve never felt anywhere near that level of enthusiasm for a sandwich since.

      *Not that kind of mushrooms

      • Whoops, didn’t mean to do ^that as a reply to someone else’s comment.

  4. I loooove @ehmanna90 ‘s ghost story and I’m super impressed that you have a service-ghost.

    I wanted to be an astronomer and now I’m a library technician. It’s actually fine ! I get to read a lot and be as antisocial as I want since I’m in technical services.

    I’m superstitious like a pigeon who thinks that pecking at a bullseye a certain way is what gives them food. That’s about all I remember about my psych 101 class.

    I would never talk about this during a first date, but for you Rachel, here’s my ghost story!

    Ghosts are definitely a thing. They make for lousy roommates because they’re up all night and have no sense of personal space.

    My mom and I lived in a haunted apartment for a while. The ghost would shake me awake and stand by my bed, waiting for me to fully wake up, then disappear. Super rude ! It got so I would only sleep on my back so she couldn’t surprise me. When my cousin who’s super psychic moved in with us for a while then it got really interesting. I think my cousin’s powers amped up the stakes or something, because both us would have these weird experiences of being yanked forcefully out of bed (all the while being actually catatonic, not fun).
    This didn’t calm down until my mom performed a little exorcism with my baptism candle and my grandmother’s prayer book. And my cousin moved out. And then _we_ moved out. Phew!

    Since then I’ve picked my apartments according to the amount of direct sunlight that enters each room, under the impression that this will actually keep ghosts at bay. I don’t know if it does but so far this superstitious pigeon has been lucky.

  5. Similar to karaoke song: “if you had to Lip Sync for your life what song would you choose?”

    • For my life? Nick Cave, something off Murder Ballads, probably Stagger Lee, including gunshots at the end

  6. I’m superstitious in that I’m a huge believer in tempting fate. My friend laughs at me for refusing to ever have my birthday party before the day of my birthday, for example.

  7. Al

    26. What is the weirdest or worst gift you have been gifted?

    80s shirt in 2005 when it still was out of style and the wrong season.

    • My ex gave me a Loverboy concert Tee from the mid 80’s in hot magenta, claiming it was worth a lot of money on the vintage market and was therefor a thoughtful gift. If anyone out there is willing to pay tons for such an artifact, let me know. It otherwise remains one of the worst gifts ever. EVER.

      • Al

        Were either of you a fan of Loverboy? Could always try to ebay or craigslist it.

        • No one was a fan of Loverboy. It was a case of thoughtlessness pushing the concept of irony down the steep slope of laziness into the ravine of broken relationships, where the irony was mangled into an unrecognisable mass of twisted wreckage and the fucking eighties. I am much more tempted to regift the shirt to someone with a note that says, “it could be worth a lot of money to the right chode” in block print magic marker.

  8. the great megan o’grady once asked me if i could play any instrument and perform any song with any band, what would it be?

    my answer (and i think it’s changed since then) was bass on “surrender” with cheap trick but i have asked a few people this question and gotten some truly amazing answers.

  9. > 7. What absurd thing did you believe was true about how the world worked as a kid?

    I used to think that people born before the introduction of color TV saw in black and white.

    • I fully believed that they invented color TV in the middle of filming The Wizard of Oz and they were just so excited about the new technology that they had to start using it right away.

  10. On my first date with a woman ever, she asked me what my first date with a woman ever was like

    I was too scared to tell her, I choked on my wine and went to the restroom

    • (I REALIZE NOW i should’ve just said “pretty good so far” or something flirty, but i was a scared tiny baby gay)

  11. 19: The tooth fairy doesn’t pay for teeth with holes in them. Turns out this was only a thing in my house.
    Sidenote, I’ve never understood the whole putting the tooth under the pillow thing that I see in movies and such. Presumably if you want your kid believing in the tooth fairy, you want them to stay asleep while you do the do tooth/money swap, so why would you put it under their pillow, where you risk waking them up. When I was growing up, a tooth that was worthy of 50c was put in a glass of water, on the windowsill, and the money was left under the glass.

  12. I sincerely hope that no one I’m ending up on a date with has read these. It’s been a day and I’m still trying to come up with an answer for nine out of ten.🤷‍♀️
    Ugh, I’m an undateable philosophical mess in some sort of pre-midlife crisis.
    I mean who IS my best friend? Where IS home? Who was I even as a child?

    P.S.:Superpower:Flying, hands down.

  13. And I believe that if ghosts exist they’re friendly and just wanna chill, or help, or be helped. Kinda like in the Sixth Sense! Maybe just less scary.

    • too many variables for solver… like, a) do they know everything they knew before but also now what happens after death, b) do they just know things based on after death like we only know things after birth, c) do they compile and learn from experiences or are they static in learning and skills, d) do they have a role or purpose or something to achieve, e) is everybody a ghost-to-be or just some people for some reason, …

      this is one of the few areas i would like to keep being happy to not know.

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