Unsure What To Ask On A First Date? Here Are 42 Ideas

Even if you’ve been on your fair share of them, it’s natural to feel nervous—maybe even anxious—before a first date. After all, you’re about to get to know someone who may potentially be your next long-term partner. The pressure of getting it right can be a lot: Will they like you? What if the vibe’s off? And in the case of awkward pauses (which there probably will be at some point), what if you run out of things to talk about? If you’re unsure what to ask on a first date to keep the conversation natural and productive, it helps to keep a few conversation starters in your back pocket.

Making a good first impression is part of what fuels first date jitters, but it’s a good thing to remember that you’re also gauging your interest in them, too. So, the questions you ask your date should be as casual as they are helpful in truly getting to know the other person. From there, you can consider if they align with your personal dating goals.

Conversation tips for the first date

Avoid treating the date like an interview

In some ways, first dates can feel like an important interview. But while you’re vetting the other person’s character, one thing to remember is you shouldn’t treat your date like it’s an interrogation. “What you don't want is a surface relationship. Keep it casual and let the conversation flow naturally,” says Jaime Bronstein, LCSW, a relationship expert, coach, and host of Love Talk Live at L.A. Talk Radio. “If the date feels like an interview, check in with yourself and ask yourself if you're having fun.” If you’re not, and it feels like you’re on the spot (and not in a good way), it might be worth asking yourself if the connection is being forced.

Get to know each other a bit before you meet

If you met this person on a dating app, you may already have an idea of what kind of things your date is into, based on their profile and your DMs. On the other hand, if your meet-cute was out in the wild—like at a bar or dog park—the information you have about them might be more limited. 

In either case, it doesn’t hurt to check in with your date before you head out to check in, go over plans, and see how the vibe flows ahead of time. Plus, it’s a great way to calm your nerves. “Have a phone or video chat before your date so that when you're on the date, you don't feel like you need to ask a million questions. [Instead,] you can focus more on having fun and interesting conversations,” says Bronstein.

Keep your values front of mind

It’s easy to get sucked into a conversation where you’re both just highlighting your accomplishments and the basics about your lives—but the tough thing is, this won’t necessarily help you figure out if you’re aligned where it counts. Try to think of what you want in a partner, and ask questions that might suss out whether they have those qualities or values. 

“Once you've got that in mind, it becomes easier to guide the conversation in a way that brings those qualities out naturally,” says Bronstein. For example, instead of asking if they’re a thoughtful person, Bronstein suggests asking something like, “How do you support your friends when they're having a hard time?” According to Bronstein, “these kinds of questions help you understand someone's true character.”

Here are some question ideas to keep your first date convos fun and interesting. 

Casual questions to ask on a first date

1. 1.
   If you had to eat one meal for the rest of your life, what would it be?
2. 2.
   How close would you say you are with your family?
3. 3.
   What was the last book you read?
4. 4.
   Where was the last place you traveled?
5. 5.
   What’s the most unusual job you’ve had?
6. 6.
   What’s your go-to comfort show?
7. 7.
   Do you have any unique or interesting family traditions?
8. 8.
   What is your friend group like?
9. 9.
   What’s your favorite thing about your best friend?
10. 10.
    What would you say is your “beige flag”?

Flirty questions to ask on a first date

1. 1.
   What’s the sexiest Halloween costume you’ve ever worn or thought about wearing?
2. 2.
   Who’s your celebrity crush?
3. 3.
   What song gets you in the mood?
4. 4.
   What is your idea of the perfect date night?
5. 5.
   What’s the most adventurous thing you’ve ever done with a significant other?
6. 6.
   Do you prefer to be the big spoon or little spoon?
7. 7.
   If you were to go on a reality dating show, which one would you apply to?
8. 8.
   What’s the steamiest sex dream you’ve ever had?
9. 9.
   What’s your most out-there fantasy?
10. 10.
    Where’s the wildest place you’ve ever hooked up with someone?

Deep questions to ask on a first date

1. 1.
   What’s one piece of advice you wish you were given sooner?
2. 2.
   What are you most proud of?
3. 3.
   When was the last time you felt truly at peace?
4. 4.
   What are you most grateful for?
5. 5.
   What is your biggest fear?
6. 6.
   If your younger self met you right now, do you think they’d be proud?
7. 7.
   What advice would you give to your younger self?
8. 8.
   What’s something you’re actively working on in yourself?
9. 9.
   What is one of your dating non-negotiables?
10. 10.
    What does a happy relationship look like to you?
11. 11.
    Who’s the first person you go to in a crisis?

Fun questions to ask on a first date

1. 1.
   What songs would you choose to be on the soundtrack of your life?
2. 2.
   If you had a podcast, who would you want to interview, and what topics would you discuss?
3. 3.
   What actor would play you in a biopic of your life?
4. 4.
   If you could know the answer to any unsolved mystery, what would it be?
5. 5.
   What is your party trick or hidden talent?
6. 6.
   What is your go-to karaoke song?
7. 7.
   When was the last time you did something for the first time?
8. 8.
   If I met your childhood friend, what story from your childhood would they likely tell me?
9. 9.
   Have you ever met a celebrity? What was that experience like?
10. 10.
    What was your favorite concert you’ve been to?
11. 11.
    What’s one thing you’re willing to splurge on?