30 First Date Questions So You Can Kiss Awkward Silences Goodbye

Try not to make it into a job interview, 'kay?
First Date Questions
Photo: Getty Images | LeoPatrizi
Jamie Cuccinelli the knot writer and wedding expert
Jamie Cuccinelli
Jamie Cuccinelli the knot writer and wedding expert
Jamie Cuccinelli
Senior Editor, Sex & Relationships
  • Jamie is a Senior Editor for The Knot where she oversees all sex and relationship editorial content.
  • Before joining The Knot Worldwide, she worked with an array of digital publications that include Brides, The Zoe Report, Bustle and MyDomaine.
  • Jamie graduated with a degree in English and Media, Culture & Communications from New York University.
Updated Sep 29, 2023

Cute outfit you feel superstar-confident in? Check. Mood-boosting playlist? Check. A group chat of friends anxiously awaiting the post-date deets? Duh. But wait! Before you head out to meet your match, there's one more must-have on your pre-date checklist: A list of first date questions to save you from any and all awkward silences. (You're welcome.)

First dates, after all, can be tricky: You obviously want to get to know the person as much as possible and keep the conversation going. But, at the same time, you don't want it to evolve into something more akin to a job interview than a fun, flirty good time. That's why we've collected this list of questions to ask on a first date: to help you learn about your potential person and your compatibility, while keeping the convo flowing and lighthearted.

For help curating the most creative first date questions, we enlisted the help of two relationship pros: Chicago sex and relationship therapist Rachel Zar, LMFT, CST, and dating expert Ismenia Meji of the podcast Paris in NYC. Scroll on to see them all—and kiss all those awkward silences goodbye.

In this article:

The Best First Date Questions

Short on time? Perhaps you're en route to the meet-up right now. Commit the best first date questions below to memory, so you have something to discuss in case the conversation lulls. Remember: Focus on open-ended questions, so neither of you is left trying to play off one-word responses.

What does your perfect Sunday look like?

"There's a lot of information to be gleaned by how someone spends their time off—and it will give you a little snapshot of what life with them might look like once you're past the dating phase." —Rachel Zar, LMFT, CST

Would you want to check out this [movie/restaurant/activity] sometime?

"By suggesting a specific second date towards the end of the night, you take the planning and guesswork out of who should reach out first. Hopefully, you'll discover a common interest throughout the date to personalize your second date idea." —Jamie Cuccinelli, Senior Sex & Relationships Editor

What made you interested in me?

"This will help you know the parts of yourself that they're drawn to and give you a sense of what they're looking for in a partner. Plus, it feels nice to get a compliment and it may inspire some flirty energy." —Rachel Zar, LMFT, CST

What are you passionate about?

"This open-ended question allows them the chance to tell you the thing they've been waiting for you to ask about. Plus, it will give you a chance to see their eyes light up in excitement. Passion is sexy!" —Rachel Zar, LMFT, CST

What are you looking for?

"In my experience in dating, I have learned that this is something that should be spoken about ASAP, so as not to waste each other's time. People generally know what they are looking for from the beginning, and it is best to know if you are on the same page with your intentions." Ismenia Meji

What's your favorite travel experience?

"If you like to travel, it's important to gauge if this person will be a good travel partner for you…and generally likes doing similar things as you." Ismenia Meji

What are your friends like?

"There is an old saying that goes, 'Birds of a feather flock together.' Usually people with similar interests, hobbies, and goals are close, therefore, giving you insight into what [your potential partner] is into without asking directly." Ismenia Meji

What do you do to relax after a long day?

"This lets you know what they like to do unwind—and how, in the future, you may be able to help them relax if they are having a stressful day." Ismenia Meji

Funny First Date Questions

Some of the best first dates afe the ones where you can't stop laughing with the other person. These funny first date questions should definitely help lighten the mood.

Would you rather have foot-long fingers or foot-long toes?

"Playing a game of 'Would You Rather?' is a great way to break the ice, get a feel for each other's sense of humor, and slip in a few questions that'll help you know their value system. It will also break up the monotony of the usual first date small talk. —Rachel Zar, LMFT, CST (You can find more "Would You Rather?" questions for couples here.)

What's your favorite dad joke?

"While something as blunt as 'What's your funniest joke?' could just make someone uncomfortable and feel put on the spot, dad jokes are supposed to be eye-roll-worthy—totally taking the pressure off." —Jamie Cuccinelli, Senior Sex & Relationships Editor

Milk or cereal first?

"Believe it or not, this question has been the cause of some strong debates! It's a good way to break the ice, and is an unexpected question that may cause your date to burst out laughing." Ismenia Meji

What's the most embarrassing song on your playlist that you love?

"I asked this on a date and was surprised to find out that my date loved blasting "Lose You to Love Me" by Selena Gomez. I did not expect that and it made me laugh! However, that vulnerability made him feel like he could continue to open up about things with me." Ismenia Meji

If you had to go on a reality show, which would you choose?

"Would they rather go on endless (and chaotic) girls' trips on the Real Housewives franchise, travel the globe on the Amazing Race, battle it out on Survivor or find love on The Bachelor? Bonus points if they can come up with their personal tagline or on-screen catchphrase!" —Jamie Cuccinelli, Senior Sex & Relationships Editor

What is your go-to karaoke song and would be willing to sing it for me right now?

"Even if your date refuses to sing the song, it will at least show you what they are into based on the song they'd choose. Are they outgoing and choose a fun and fast-tempo song, or are they more laid-back?" Ismenia Meji

What was the last thing you Googled?

"Fine, twist my arm: If this question was posed to me right now, my answer would be "How much is $175,000 in 1996 worth today?" (I was just watching The Craft, okay?) —Jamie Cuccinelli, Senior Sex & Relationships Editor

Spicy Questions to Ask on a First Date

If things are going well and you're both comfortable with getting a little flirty—or even sensual—consider the spicy questions to ask on a first date below. (Again, mutual comfort is key!)

What's the first thing you noticed about me?

"Just the right amount of flirty, this question opens up the floor for you to flatter your partner with what attracts you to them, too." —Jamie Cuccinelli, Senior Sex & Relationships Editor

How important is sex to you in a relationship?

"This is where you can start to explore sexual compatibility before things actually heat up—and without getting too explicit. Do you feel aligned in terms of the value you put on sex? Or are their expectations far from what you know to be your reality?" —Rachel Zar, LMFT, CST

How do you like to be touched?

With consent a given, Rachel Zar suggests, "For added flirtation, add some actual touch on their arm to demonstrate. Do they prefer a soft tickle or a firm massage? Incorporating playful touch on a first date will help you get a sense of the chemistry between you."

What's the most attractive quality you look for in a person?

"This will tell you if the person is more interested in appearance, or if they are turned on by other qualities like a sense of humor or sarcasm." Ismenia Meji

Deep First Date Questions

Don't be nervous! If the vibes are right, open up to your partner and learn more about the true them via some deep first date questions.

What is something you're working on in yourself?

"Self-awareness and humility can be very attractive qualities in a partner. Relationships require a ton of work on ourselves, and this question will help you see if the person you're sitting with has already started that process." —Rachel Zar, LMFT, CST

Who are you when no one is around?

"This opens up the conversation to allow your date to be vulnerable and express any quirks they may have. This may also give you some insights into how they view themselves." Ismenia Meji

What do you like most about yourself?

"Give your date a chance to brag! You'll also get a sense of their value system from their answer. Do they prioritize their sense of humor or their altruism? Are they most proud of their degree or their friend group?" —Rachel Zar, LMFT, CST

What is something you've always wanted to do but were afraid to?

"This provides insight into their wildest dreams and desires—and proves that being vulnerable can be kind of fun." —Jamie Cuccinelli, Senior Sex & Relationships Editor

What do you value the most in a friendship?

"This will give you insight into what that person sees as a priority. Is loyalty important to them? Or do they look for people that listen to them?" Ismenia Meji

What do you think is the key to a healthy relationship?

"This will give you a sense of how much they've learned from past relationships and the type of effort they're willing to put into yours if this works out. Plus, you'll see if the things they value in a relationship align with yours." —Rachel Zar, LMFT, CST

What's an accomplishment that you are proud of in your life?

"This will give you the opportunity to show interest by asking follow-up questions about how they were able to accomplish their goal. It will also put them in a good mood as they are talking about an experience that they cherish." Ismenia Meji

Is there someone that you are not 100% over?

"Some individuals may not be open to answering (or asking) this question on a first date. But if they do, you can gauge where their head is at and what their intentions may be in dating. If they are still hoping to rekindle a past love, they may just be looking for a distraction or someone to have fun with." Ismenia Meji

Romantic Questions to Ask on a First Date

Is a second date seemingly on the horizon? It might be time to pull out these romantic questions to ask on a first date—and lock in that sequel.

What is your love language?

"This will tell you what you can do to make them feel loved and appreciated if the relationship continues to grow. It will also tell you if you're compatible: If you are not a person who is very expressive and your date's love language is words of affirmation, and you know it may be harder for you to fulfill that. However, if you know this about yourself and really like this person, then you'll know what to work on to ensure the relationship progresses." Ismenia Meji

What is romantic to you?

"Everyone has their own idea of what romance means to them. For some, it may be finding random love letters in their purse or wallet. For others, it may be receiving a text asking if they had lunch already. It is good to know what your date values and finds romantic." Ismenia Meji

If you could whisk me away on a spontaneous getaway right now, where would we go?

"This will let you know if they are spontaneous and what their travel preferences are. Do they prefer to go on an adventure and climb a mountain? Or are they more laid-back and prefer to go to a Caribbean Island and lay on the beach?" Ismenia Meji

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