Questions to Ask on a First Date

Start here. These are easy, low-pressure questions to get the conversation flowing.

1. What’s keeping you busy these days outside of work?
2. What’s the best thing that happened to you this week?
3. Are you from around here, or is there a more interesting origin story?
4. What do you do for fun when you’re not on dates with strangers?
5. How would your best friend describe you in three words?
6. What’s the last show you completely binge-watched?
7. Are you a planner or more of a spontaneous person?
8. What kind of music are you into right now?
9. Do you cook, or are you more of a takeout person?
10. What’s something you’re looking forward to this month?

When the conversation feels right, go deeper. These questions build real connection. See our full list of deep first date questions.

1. What’s something you believed as a kid that shaped who you are today?
2. What does a meaningful life look like to you?
3. What’s the hardest lesson you’ve ever had to learn?
4. What’s something most people don’t understand about you?
5. What are you most proud of that has nothing to do with work?
6. Do you think people can truly change?
7. What makes you feel truly seen by another person?
8. What’s the bravest thing you’ve ever done?
9. What part of yourself are you still trying to figure out?
10. What’s a value you’d never compromise on, even for love?

Keep the energy light and playful with these. More at fun first date questions.

1. If your life was a movie, what genre would it be?
2. What’s the most spontaneous thing you’ve ever done?
3. If you could have any superpower — but only a really lame one — what would it be?
4. What’s the most useless fact you know?
5. If you could swap lives with any celebrity for a day, who?
6. What fictional world would you want to live in?
7. What’s the worst haircut you’ve ever had?
8. If aliens asked you to explain humanity in one sentence, what would you say?
9. What’s a trend you absolutely refuse to follow?
10. Dogs or cats — and why is your answer correct?

Laughter is the fastest way to build chemistry. Try our funny first date questions page for more.

1. What’s the most embarrassing song on your playlist right now?
2. What’s your most unpopular food opinion?
3. What’s the weirdest thing you’ve ever Googled?
4. If you won the lottery tomorrow, what’s the first ridiculous thing you’d buy?
5. What’s the strangest compliment you’ve ever received?
6. If your pet could talk, what would it say about you?
7. What app on your phone do you waste the most time on?
8. What’s a hobby you secretly want to try but are embarrassed about?
9. What’s the best prank you’ve ever pulled or fallen for?
10. What show have you rewatched an embarrassing number of times?

When you want the conversation to go somewhere meaningful. See all romantic first date questions.

1. What does your ideal Sunday morning look like with someone you love?
2. How do you know when you’re falling for someone?
3. What’s a small gesture that means more to you than any grand romantic act?
4. What does a perfect date look like in your mind?
5. What song reminds you of being in love?
6. Do you think the best relationships are built on passion or friendship?
7. What makes you feel really connected to someone?
8. What’s one thing about you that you hope someone will fall in love with?
9. What would make tonight the perfect first date?
10. If we had no plans and nowhere to be, how would you want to spend the day together?

Tailored for asking guys specifically. Full list at questions to ask him.

1. What’s the most thoughtful thing you’ve done for someone you were dating?
2. What’s your idea of being a good partner?
3. How do you handle conflict in a relationship?
4. What did your dad teach you about relationships?
5. Are you the type who plans the dates or prefers to be surprised?

Thoughtful questions for asking women. See more at questions to ask her.

1. What’s a compliment you never get tired of hearing?
2. What’s one thing you want in a partner that most people wouldn’t list?
3. When do you feel the most confident?
4. What made you say yes to this date?
5. What’s a cause or passion you really care about?