First Date Questions: What to Ask to Really Get to Know Someone

You've picked the place, survived the outfit crisis and made it through the first awkward hug. Now you're sitting across from each other, drinks in hand, and there's a pause. Everyone has felt that pause. The good news: one well-chosen question can turn it into a three-hour conversation you don't want to end. Here are 75 first date questions, from easy icebreakers to deeper ones, plus the part most lists skip: how to actually ask them so your date feels like a conversation, not a job interview.

What makes a good first date question?

The best questions to ask on a first date are open-ended, a little personal and easy to answer with a story instead of a single word. "Do you like your job?" gets a yes or no. "What's the best part of your job that nobody talks about?" gets a story, an opinion and probably a laugh. That's the difference between a question that fills silence and one that tells you who someone actually is.

A good first date question also gives you something to share back. Conversation is a tennis match, not a quiz. And if you want a head start before you even meet, the Bebs dating app lets you take a compatibility test with your match, so you show up already knowing where you click and where you'll probably have a fun debate.

Easy icebreaker questions to start the conversation

Start light: in the first fifteen minutes, the goal is to relax, not to dig deep. These questions are easy to answer, impossible to get wrong and almost always lead somewhere.

1. What was the best part of your week so far?
2. How do you usually spend a free Saturday?
3. What's your go-to order at a place like this?
4. What show are you watching right now?
5. What song is stuck in your head this week?
6. Are you a morning person or a night owl?
7. What's the best thing you've eaten lately?
8. How long have you lived in this city, and what do you love about it?
9. What's a hobby you've picked up recently?
10. Coffee, tea or energy drinks: who are you?

Fun first date questions

Fun first date questions show you someone's sense of humor, which is one of the clearest signals of chemistry. If you're both laughing at question three, that's a very good sign.

1. What's your most controversial food opinion?
2. If you could only eat one cuisine for the rest of your life, what would it be?
3. What's the most "you" thing you've ever done?
4. What's a weird skill you have that nobody expects?
5. Which fictional world would you most want to live in?
6. What's your karaoke song, and how committed are you to it?
7. What's the worst trend you fully participated in?
8. Would you rather have a rewind button or a pause button for your life?
9. What's your toxic trait, but make it cute?
10. What would your friends say is your most beige flag?

First date questions to get to know someone

Once you're both comfortable, shift to first date questions that reveal what someone values, how they spend their time and what makes them light up. Listen for the details: they're what you'll bring up on date two.

1. What do you do for work, and what's the part you actually enjoy?
2. What are you most excited about right now?
3. What does a perfect day look like for you?
4. Who's the person you text the most?
5. What's the best trip you've ever taken?
6. Where's somewhere you've always wanted to go?
7. What did you want to be when you were a kid?
8. What's something you could talk about for an hour?
9. How do you recharge after a long week?
10. What's a book, movie or podcast that changed how you think?
11. Are you close with your family?
12. What's something you're proud of that isn't on your résumé?
13. What's a skill you want to learn this year?
14. What's your love language when it comes to friends?
15. What made you say yes to this date?

Deeper first date questions (if the vibe is right)

Deep first date questions work best later in the evening, once you both feel relaxed and the conversation is already flowing. Read the room: if they're giving short answers, keep it light. If they lean in, go for it.

1. What's something you believed five years ago that you don't anymore?
2. What's the best advice you've ever gotten?
3. When do you feel most like yourself?
4. What does a good life look like to you?
5. Who has shaped you the most?
6. What's a risk you're glad you took?
7. What's something small that instantly makes your day better?
8. What are you working on in yourself right now?
9. What does friendship mean to you?
10. What are you looking for when you date?

First date questions to ask her

The best first date questions to ask a girl are about her passions and her opinions, not just her looks or her job title. Most women get the same three questions on every first date. Being the one who asks something she actually enjoys answering is how you stand out.

1. What's something you're really good at that you rarely get to talk about?
2. Who's the funniest person in your life?
3. What's a hill you would die on?
4. What's your favorite way to spend a rainy day?
5. What's the last thing that made you laugh out loud?
6. What's on your list of things to do before thirty, or before next summer?
7. Which friend would you call first with big news?
8. What's a place in this city you think is underrated?
9. What's your comfort movie?
10. What's something you wish more people asked you about?

First date questions to ask him

Good first date questions to ask a guy invite him to tell stories, because many men open up far more through stories than through direct "how do you feel" questions.

1. What's the most spontaneous thing you've ever done?
2. What's a project you're secretly obsessed with?
3. What's the best concert or game you've ever been to?
4. Who's your best friend, and how did you meet?
5. What's something you can cook really well?
6. What's a goal you're quietly working toward?
7. What's the best road trip you've ever been on?
8. What's something you've changed your mind about recently?
9. What's a compliment you've never forgotten?
10. What does your ideal weekend away look like?

Questions to ask on a first date with someone you already know

When your first date is with a friend, a coworker or someone from your circle, skip the basics and ask questions that show a side of them you haven't seen yet.

1. What's something about you most people in our group don't know?
2. What was your first impression of me?
3. What are you like when you're completely off duty?
4. What's a dream you haven't told many people about?
5. What's your family like?
6. What do you do when nobody needs anything from you?
7. What's a moment you've been really proud of this year?
8. What's something you've always wanted to try but never had anyone to do it with?
9. When did you first think about asking me out, or saying yes?
10. What should we do on a second date?

And one more for anyone, any date: 75. "What's a question you wish people asked you more often?" It's the perfect fallback, and their answer tells you exactly what to ask next.

How to ask first date questions without it feeling like an interview

The secret isn't the questions themselves, it's what you do after they answer. A first date goes wrong when one person fires off question after question and the other feels like they're being screened for a job. It goes right when every answer becomes a thread you both pull on.

Follow up before you move on. If they say they just got back from Mexico City, don't jump to "So what do you do for work?" Ask what surprised them, what they ate, whether they'd go back. Share your own answer too: if you ask about their worst travel story, be ready with yours. And don't be afraid of a pause. A few seconds of silence while you both smile is part of the date, not a sign it's failing.

Finally, pay attention to what lights them up. When someone's answers get longer, faster and more animated, you've found a topic worth staying on. That's also your cheat sheet for the follow-up text and the second date.

What not to ask on a first date

Avoid questions that feel like an evaluation or that drag the conversation into heavy territory too soon. "How much do you make?", "Why are you still single?" and "Do you want kids, and when?" all have a place in a relationship, just not in the first hour of meeting someone. Skip the deep dive into exes too. A light "How long have you been on the apps?" is fine. A detailed review of their last breakup is not.

After the questions: what comes next

The best first dates end with both people already thinking about the next one. If the conversation flowed, say so: "I had a really good time, I'd love to do this again." Then follow up with a text that mentions something from your conversation. Not sure what to say? Here's our guide on what to text after a first date, and when you're ready, our second date ideas will help you plan round two.

In the Bebs dating app, you can book a table at Olive Garden or Red Lobster and send the invite right in the chat, or find a concert or comedy show on the events map and grab tickets in a few taps. The questions you asked tonight will tell you exactly which one they'd love.

Skip the small talk before you even meet

Take a compatibility test with your match in the Bebs dating app and walk into your first date already knowing where you click. Then book the table right from the chat.

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