The 27 Best and Worst First Date Questions You Could Possibly Ask

Some guys have a knack for first dates. They can seamlessly navigate conversations so topics flow from one to the next without any lulls.

They effortlessly balance talking about themselves while still learning about their partner. They’re charming, funny, and quick-witted. They just really have it down.

Then there’s the rest of us, who might need a little help on first dates when the prolonged silence with our partner sounds deafening. Sometimes, the conversation doesn’t naturally progress, and that’s okay! That doesn’t mean you aren’t “right” for each other. It doesn’t mean the date is going poorly. It probably means you’re both a little nervous and need help coming up with questions to ask—that’s all!

If you find yourself in a bind on a first date, not sure of what to say, here are 27 questions that should hopefully get you and your partner talking again. These questions aren’t the run-of-the-mill options you’ve heard a zillion times before, like “What do you do for work?” They’re ideal questions to ask if you really want to get to know your partner. (We also provided three bonus questions of what to definitely not ask your partner.)

To help learn the best first date questions, we spoke to two relationship experts: Maria Sullivan, VP of Dating.com and Amanda Bradford, founder and CEO of the dating app, The League. Together, they provided great first date questions and explained why they’re great first date questions.

The Best Questions to Ask on a First Date

1. What’s been your favorite vacation?

Why it’s good to ask: “Everyone loves going on vacation and talking about what they did that made it so great,” Sullivan says. “Asking this question on a first date will open up a conversation about where your date has traveled and

if you are both into the same types of vacation destinations.”

2. What’s your dream travel destination?

Why it’s good to ask: “Talking travel really works,” Bradford adds“In one study, 18% of couples on first dates who discussed travel wanted to go on a second date. In contrast, less than 9% of couples who talked about movies wanted to go out again.”

3. What are you currently obsessed with?

Why it’s good to ask: Whether it’s a book, TV show, or crossfit, odds are, there’s something that your date is currently into. People like to share their interests, and it’s a good way to see if you two share any of the same interests.

4. What are you most passionate about?

Why it’s good to ask: “People love discussing the hobbies and pursuits they enjoy,” Bradford says. “If you want to know who someone is, find out what they love.”

5. What types of things do you find funny?

Why it’s good to ask: If you two share a sense of humor, you’re golden. Humor is something that really bonds us with other individuals. Think about it. You probably end up laughing a bunch with your best friends whenever you hang out. That’s part of the reason why you enjoy spending time with them as much as you do. So if you and your date find the same things funny, you can absolutely bond over that.

6. Are you a morning person or a night owl?

Why it’s good to ask: “Some people are able to wake up at the crack of dawn while others are able to stay awake until the crack of dawn,” Sullivan says. “Asking your date this question will give you an idea of their daily schedule. For example, are they up early at the gym or up late binge-watching their favorite shows?” This can help determine if you two are compatible with one another.

7. If you could spend an afternoon with anyone dead or alive, who would it be?

Why it’s good to ask: This hypothetical lets your date talk to you about someone that they admire. Perhaps they say it’s their grandpa who they’ve never met or they say a celebrity or activist or notoriously evil person, to learn why they did what they do. No matter who they respond, it opens up the conversation.

8. Who should play you in the movie of your life?

Why it’s good to ask: “This fun ‘what-if’ question caters to their ego—and the actor they choose clues you in on how they see themselves,” Bradford says.

9. What do you value most in a friendship?

Why it’s good to ask: This really tells you what type of person they are. Do they value honesty, integrity, humor, partying, something else? It also gives you a sense of whether or not you’d vibe well with your date’s friends, which could be important down the line.

10. What’s the most interesting fact you know?

Why it’s good to ask: “People are full of interesting facts,” Sullivan says. “This is a fun question to ask to find out what your date knows, and you might even learn something new.” Additionally, everyone loves coming across as interesting. It’s great you’re giving your date the opportunity to do so.

11. What’s your greatest accomplishment?

Why it’s good to ask: This gives your date the opportunity to humble brag! It also gives you a sense of how hard they are willing to work to get whatever it is that they want.

12. Who did you see for your first concert?

Why it’s good to ask: “Music is a great date topic,” Bradford explains. “Prepare to be impressed that they saw Beyoncé, or saddened that they saw Nickelback.”

13. What’s your most treasured memory?

Why it’s good to ask: First off, simply talking about their most treasured memory will put them in a good mood. But it will also provide insight into what they hold most dear—be it family, friends, work, or something else.

14. What was the best day of your life?

Why it’s good to ask: “This question takes your date back in time to a big life moment that they’ll love reliving,” Bradford says. “It goes much deeper than surface-level chat, and this deeper dive makes you stand out from other guys this person has been going on dates with.”

15. What’s your favorite holiday?

Why it’s good to ask: “This question can give you insight into your date’s religion based on the answer, which can be an important part of a relationship,” Sullivan says. It also opens up to a conversation about religion, which yes, could be a lot on a first date, but also might not be. You’ll have to gauge to see if you should take the conversation there.

16. What’s the best gift you’ve ever given someone?

Why it’s good to ask: “They’ll get to brag a bit while feeling very generous,” Bradford says. It’s also a big red flag if they haven’t given anyone anything before.

17. What do you love most about your job/career?

Why it’s good to ask: “This question lets you talk about work in a positive, emotionally evocative way, rather than boringly asking, ‘So, what do you do?’” Bradford says.

18. What were you like as a kid?

Why it’s good to ask: “Sharing stories from childhood gives them a chance to be vulnerable by giving you a glimpse of their younger self,” Bradford explains. “You’re helping them connect with you and with their younger self.”

19. What does your ultimate favorite meal consist of?

Why it’s good to ask: “Who doesn’t love food?” Sullivan asks. “This question will allow you to figure out what types of food you have in common and if things go well, it can even help you decide where to go on your second date.”

20. What’s your hidden talent?

Why it’s good to ask: “This allows them to show off while sharing a secret—and sharing personal secrets can build trust and connection,” Bradford says.

21. Would you rather…?

Why it’s good to ask: “A first date should be fun, and good ‘Would You Rather’ questions get your date laughing,” Bradford says. “A 2014 study found that women are drawn to men with a sense of humor. Here are some fun examples!” Bradford recommends:

The Worst First Date Questions

1. Why are you single?

Why you shouldn’t ask: “Although this question may seem harmless, it may leave your date feeling awkward and unsure how to answer,” Sullivan says. It also can be read as an insult. In essence, you’re asking, “So what’s wrong with you?”

2. How many exes do you have?

Why you shouldn’t ask: “Asking this personal of a question on a first date can be a big red flag,” Sullivan says. “It is important to take your date’s privacy into consideration and not ask anything that might make them feel uncomfortable.”

3. How much money do you make?

Why you shouldn’t ask: “Someone’s income is not an important piece of information for a first date and may make you seem like you are more interested in money than the actual person,” Sullivan explains. “Spend the first date asking questions that will allow you to learn more about your date’s heart, not their wallet.”