What To Ask On A First Date

From flirty to thoughtful, these 42 questions will help you skip small talk and actually connect.

Author

Audrey Sawyer
May 15, 2025

Even the most confident daters can feel a twinge of anxiety before a first date. It’s natural you’re hoping for a spark, trying to be yourself, and figuring out if there’s potential for more, all while trying not to run out of things to talk about. The good news? A little preparation can go a long way, especially when it comes to keeping the conversation flowing.

Whether your date is with someone you matched with online or someone you met IRL, having a few go-to questions in your back pocket can ease the pressure and even turn awkward silences into meaningful moments.

First Date Talk: The Goal Isn’t Perfection It’s Connection

Instead of aiming to impress or over-prepare, focus on asking open-ended questions that help you get a genuine sense of who the other person is. According to relationship expert Jaime Bronstein, LCSW, a good first date shouldn’t feel like a job interview. “What you don't want is a surface relationship,” she says. “Keep it casual and let the conversation flow naturally.”

To avoid that interview vibe, Bronstein suggests:

  • Doing a low-pressure check-in beforehand even a short phone or video call can help ease nerves.

  • Keeping your values top of mind ask questions that align with what you're looking for in a partner.

  • Swapping “what do you do” for “who are you really” personality-revealing questions make for deeper, more fun conversations.

And if you’re not feeling it? That’s okay too. Part of dating is figuring out who’s not your person.

42 Questions To Ask On A First Date

These are grouped by vibe, so whether you're going for lighthearted or introspective, you'll be ready.

Casual Conversation Starters

  1. If you had to eat one meal for the rest of your life, what would it be?

  2. How close are you with your family?

  3. What was the last book you read?

  4. Where’s the last place you traveled to?

  5. What’s the most unusual job you’ve had?

  6. What’s your comfort TV show?

  7. Do you have any quirky family traditions?

  8. What’s your friend group like?

  9. What’s your favorite thing about your best friend?

  10. What would you say is your “beige flag”?

Flirty and Fun

  1. What’s the sexiest Halloween costume you’ve ever worn (or wanted to)?

  2. Who’s your celebrity crush?

  3. What song always gets you in the mood?

  4. Describe your ideal date night.

  5. What’s the most adventurous thing you’ve done with a partner?

  6. Are you more of a big spoon or little spoon?

  7. Which dating reality show would you join?

  8. What’s the steamiest dream you’ve ever had?

  9. What’s one fantasy you’ve never shared?

  10. Wildest place you’ve ever hooked up?

Deep & Thought-Provoking

  1. What’s one piece of advice you wish you'd gotten earlier in life?

  2. What are you most proud of?

  3. When was the last time you truly felt at peace?

  4. What are you most grateful for?

  5. What’s your biggest fear?

  6. Would your younger self be proud of who you are today?

  7. What advice would you give your younger self?

  8. What’s something you’re currently working on in yourself?

  9. What’s a dating non-negotiable for you?

  10. What does a happy relationship look like to you?

  11. Who do you call when life gets messy?

Playful & Imaginative

  1. What songs would be on the soundtrack of your life?

  2. If you had a podcast, who would you interview and what would you talk about?

  3. Who would play you in a movie about your life?

  4. If you could solve one unsolved mystery, what would it be?

  5. Got any hidden talents or party tricks?

  6. What’s your go-to karaoke song?

  7. When was the last time you did something for the first time?

  8. What story would your childhood best friend tell about you?

  9. Ever met a celebrity? What happened?

  10. What’s the best concert you’ve ever been to?

  11. What’s one thing you’ll always splurge on?

Let the Conversation Lead the Way

You don’t need to ask all of these or even most of them. The point is to use them as gentle guidance to spark authentic conversations. Let your date talk, listen actively, and follow up with your own stories. Great first dates don’t come from perfect questions; they come from mutual curiosity and a sense of ease.

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