The 21 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. If you find yourself in a bind on a first date, not sure of what to say, here are 20 questions that should hopefully get you and your partner talking again. These questions aren’t the boring “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.)

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,” says Maria Sullivan, Dating Expert and VP of Dating.com. “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,” adds Amanda Bradford, founder and CEO of the dating app, The League. “In one study, 18% of couples on first dates who discussed travel wanted to go a second date. In contrast, less than 9% of couples who talked about movies wanted to go out again.”

3. What are you most passionate about?

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

4. Are you more of a morning or night person?

Why it’s good to ask: Some people are able to wake up at the crack of dawn while other are able to stay awake until the crack of dawn,” says Sullivan. “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.

5. 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,” says Bradford.

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

Why it’s good to ask: People are full of interesting facts,” says Sullivan. “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.

7. Who did you see for your first concert?

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

8. 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,” says Bradford. “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.”

9. 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,” explains Sullivan. It also opens up to 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.

10. 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.

11. 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?’” says Bradford.

12. 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,” explains Bradford. “You’re helping them connect with you and with their younger self.”

13. What does your ultimate favorite meal consist of?

Why it’s good to ask: “Who doesn’t love food?asks Sullivan. “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.”

14. 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,” says Bradford.

15. 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:

“Would you rather have a snowball fight or a food fight?”

“Would you rather walk in on your parents having sex, or they walk in on you having sex?”

“Would you rather have eight arms or be a cyclops?”

16. What do you usually do on weekends?

Why it’s good to ask: This question gives you a chance to see if you have matching lifestyles. If your partner’s weekends consist of reading in bed whereas most weekends you’re out at the club drinking with friends, then they might not be the right person for you. If you do have similar weekends, then the conversation will naturally flow from there. For example, if you both like reading, you’ll be able to discuss your favorite books. If you both like going out, you can talk about your favorite bars.

17. What’s on your bucket list?

Why it’s good to ask: This question now only gives you a sense of your partner’s interests, it also provides great ideas for date number two. If you really like them after the first date, sky diving might not be that crazy of idea if that’s something they’ve always wanted to try out.

18. Want to share an embarrassing moment?

Why it’s good to ask: On dates, we try to present the best version of ourselves, as we should, but sometimes, it can get a little too serious and even start to sound a little “braggy.” This question helps you and your partner be vulnerable with one another, breaking down any facades.

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,” she 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,” she says. “It is important to take your dates 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,” she explains. “Spend the first date asking questions that will allow you to learn more about your date’s heart, not their wallet.”

 

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