If you feel burned out on coming up with questions for a first date, you’re not alone! The ritual of first dates can often feel repetitive and lackluster. There are only so many ways to ask a version of so what are your interests? And if you’ve already been chatting a bit on the apps or during the lead up to a date (which, for the record, I somewhat advise against unless that’s truly your preference for getting to know someone!), it can be even harder to know what to say on a first date. But asking questions is important. If you show up to a date and only answer the other person’s question or otherwise only talk about yourself, trust you’re probably about to get subtweeted or roasted in a group chat. There is no perfect roadmap for how to crush a first date, but the number one thing you can do to at least ensure a baseline decent experience is ask your date(s) about themselves!

The questions below are designed to inject some life and creativity back into your first date question asking if you’re feeling stuck or stalled in the dating process. You can ask them word for word or use them to riff and come up with your own against-the-grain questions. They’ve been divided into a few categories: chill, pop culture, strange, spicy, and misc. So take what you need and leave what you don’t! Some include follow-up questions, so really you’re getting even more than 50 prompts for first date conversation! For some of these, you might be wondering what makes them specifically gay. Well, I wrote them and I’m gay. Hope that helps!

Get ready to crush this first date! You’re gonna do great!

Chill Questions

These are casual, get-to-know-you questions that are at least slightly more interesting than the general/obvious ones like “what do you do?” Start with these if you want to ease into deeper conversation or if you like to generally take a more chill approach on first dates.

1. How did you meet your best friend?
2. What’s your favorite book?
3. What are your favorite things to do on your days off?
4. What did you do today before this date?
5. What was the last thing that made you laugh?
6. What kind of cake do you like to have for your birthday? Or if not cake, what do you like to have?
7. Do you collect anything?
8. What are your favorite qualities in other people?
9. What’s your favorite photo of yourself?
10. Do you keep a journal?

Pop Culture Questions

Books, movies, television, music, etc. tend to be pretty fun and easy topics for first dates! Here are some pop culture-themed questions you can ask to get to know your date’s interests and tastes!

1. Who is your celebrity crush? Who was your first queer celebrity crush?
2. What album could you listen to on repeat for an entire day?
3. What’s the first gay kiss you can remember seeing in a movie or on television?
4. What’s your go-to karaoke song?
5. What’s a gay movie you know is “bad” but you love anyway?
6. What queer book that hasn’t been made into a series/movie yet do you think should be made into a series/movie?
7. What queer actor should play you in a biopic about your life?
8. What’s an unpopular opinion you have about a piece of queer pop culture?
9. If your life were a television show, what would be the theme song?
10. How many films from the Autostraddle Encyclopedia of Lesbian Cinema have you seen? (This question provides a built-in activity! You can scroll through the list together! And also make plans to watch some movies together!)

Strange Questions

Want to be memorable? Want your date to think you’re creative and surprising? Ask some of these hyperspecific, open-ended, or just downright weird (in a fun way) questions! Treat your date conversation like a creative writing prompt!

1. Have you ever seen a ghost or experienced a haunting?
2. Do you have any stories about cryptids?
3. What are your thoughts on time travel? If there were zero consequences to the current timeline, would you rather time travel to the past or the future?
4. Do you have any weird stories about birds?
5. If you were a piece of furniture, what would you be?
6. If you had a pet sloth, what would you name it?
7. What do you imagine the bottom of the deepest part of the ocean looks like? (Here’s another activity question: Have them draw it! Doesn’t matter if they’re bad at drawing, that almost makes it more fun.)
8. Do you own any cursed artifacts?
9. Who’s your nemesis?
10. What if we kissed at the Lowe’s Garden Center?

Spicy Questions

Listen, some of us like to jump right to the sexy chase on a first date. If that’s you and your date also gives off a vibe of talking about sex openly, add a little spice to the convo with these questions.

1. What was the last sex dream you had?
2. What’s the weirdest sex dream you’ve had?
3. What’s your favorite non-Hitachi sex toy?
4. What do you think is your sexiest quality?
5. What’s something sexual you’ve always wanted to try but haven’t?
6. Where’s the weirdest place you’ve had sex?
7. What’s a recurring fantasy you have?
8. What songs turn you on?
9. What’s your favorite sex scene from a movie?
10. Have you ever crushed on someone you shouldn’t have?

Miscellaneous Questions

These first date questions don’t necessarily fit into any of the categories above! They might not be openers like the chill questions, but they could work once you’re a few questions in.

1. Can you remember any of your dreams from last night and if so what were they about? (Or, what’s the last dream you can remember?)
2. What’s the worst first date you’ve ever been on?
3. How did you decide what to wear to this date?
4. Do you read tarot?
5. What are your thoughts on astrology?
6. What’s your favorite thing about yourself?
7. What’s the worst gift you’ve ever received?
8. What’s the biggest misconception about you?
9. How do you organize your bookshelves?
10. What’s something you’ve lost that you’re still upset about?

Have a good go-to first date question that often leads to a second date? Let’s hear it in the comments.

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