75+ Funny & Flirty Questions to Ask on a First Date

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Conversation starters to break the ice and make a good impression

Co-authored by Lauren Sanders and Annabelle Reyes

Last Updated: September 8, 2024 Fact Checked

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Lighthearted & Casual Questions

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Deep Get-to-Know-You Questions

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Romantic & Flirty Questions

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Funny & Unique Questions

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Tips for Making Great Conversation

If you’ve got a first date coming up, you’re probably feeling pretty excited, but you may also be a little nervous about keeping a good conversation going. You’ve come to the right place! We’ve compiled a thorough list of questions to ask on a first date, so that you can connect with the other person and get to know them better. We’ve also included expert insights from professional matchmakers and dating coaches about how to make great conversation, so keep reading!

Ice Breaker Questions for a First Date

What do you like to do in your free time?
What’s your favorite vacation destination?
Who’s your celebrity crush?
What’s your favorite type of music to listen to?
What has been the highlight of your week so far?
What’s your favorite way to spend a Saturday?
Are you more of an indoorsy or outdoorsy person?

Section 1 of 5:

Lighthearted & Casual Questions to Ask a Date

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Start with lighthearted questions to get a good convo going. At the beginning of the date, you probably don’t want to jump straight into super serious questions—this may intimidate the other person. Instead, start with a few casual and lighthearted questions to break the ice, start getting to know them, and establish good vibes for the rest of the date.^{[1]
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Research source} Here are few examples:
- Do you have any fun hobbies you like to do in your free time?
- What are your favorite things to do on the weekends?
- What’s your favorite way to unwind after the work day?
- Are you more of a cat person or dog person?
- What’s your favorite place to travel to?
- What’s the coolest vacation experience you’ve ever had?
- If you could be best friends with any celebrity, who would you pick?
- What kind of music do you like to listen to?
- What movie could you watch over and over again?
- What’s the last TV show you binge watched?
- Have you read any good books lately?
- Do you prefer to listen to music or podcasts in the car?
- What’s the best concert you’ve ever been to?
- What’s your favorite meal of all time?
- Do you have a favorite restaurant?
- What’s your most controversial take on a popular food?
- Do you like cooking, or do you prefer takeout?
- Do you have any hidden talents?
- Are you more of an indoorsy or outdoorsy person?
- Are you more of a morning person or night owl?
- What’s been the highlight of your week so far?

Section 2 of 5:

Deep Get-to-Know-You Questions to Ask a Date

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Once you’ve broken the ice, ask deeper questions to get to know them. It’s still a first date, so you don’t need to jump into super serious topics, but it’s definitely appropriate to ask a few questions about their personality, values, and experiences. This helps you learn more about them and connect over things you have in common.^{[2]
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Research source}
- Do you consider yourself more of an introvert or extrovert?
- Do you like to plan things out, or do you prefer going with the flow?
- What do you value most in a relationship or friendship?
- If you had to list your 3 favorite things about yourself, what would they be?
- What’s the best piece of advice you’ve ever received?
- Who has been the biggest role model in your life?
- If you could talk to your younger self, what would you say?
- Do you have a favorite childhood memory?
- Did you play sports growing up?
- What was your favorite class in school?
- Do you have any siblings, and are you close to them?
- What traits do you admire most in others?
- What’s your favorite place in the world, and why?
- Who are the people in your life who are most special to you?
- What would you say you’re most grateful for right now?
- If you picture your life 5 years from now, what does it look like?
- What’s the biggest goal you’re working toward right now?
- What’s one thing you want to learn, or a skill you want to improve?
- What’s an achievement you’re really proud of?
- What’s something you’ve always wanted to do, but you were too afraid to try?
- What’s the biggest lesson you’ve learned from a past friendship or relationship?
- What are you most passionate about right now?

Section 3 of 5:

Flirty & Romantic Questions to Ask Your Date

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If you’re really connecting, ask flirty questions to turn things up a notch. Research shows that engaging in reciprocal self-disclosure (revealing personal information to each other) increases feelings of closeness.^{[3]
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Trustworthy Source

Greater Good in Action
An initiative by UC Berkeley's Greater Good Science Center promoting science-based practices for a meaningful life

Go to source} In other words, once you’ve spent a bit of time sharing about yourselves, you may start to feel like you’re connecting on a deeper level. If romantic feelings are flowing between the two of you, consider asking a few questions about love and relationships.
- What do you think your love language is?
- What qualities do you look for in a significant other?
- Do you think you have a specific “type”?
- What does romance mean to you?
- How important do you think physical compatibility is in relationships?
- What’s the first thing you noticed about me when we met in person?
- What drew you to me?
- In your opinion, what’s the most attractive quality a person can have?
- Do you believe in love at first sight or soulmates?
- What’s your favorite love song of all time?
- What’s your communication style in a relationship?
- Do you like big romantic gestures, or do you prefer more low-key shows of affection?
- What would your ideal romantic date look like?
- Do you prefer casual or fancy date nights?

Section 4 of 5:

Funny & Unique Questions to Ask Your Date

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If the conversation lags, shake things up with a funny question. A silly or unique question can help get things flowing again and lead you down some interesting conversational avenues. It can also help you figure out if the two of you have a similar sense of humor.
- What’s the most embarrassing story you can think of from your childhood?
- What was the craziest online dating or blind date experience you’ve ever had?
- If you could have any superpower, what would you choose?
- If you could take a one day vacation to a different time period, what era would you pick?
- Were you more of a Disney Channel, Nickelodeon, or Cartoon Network person when you were growing up?
- Who would you say is your celebrity lookalike?
- If you won the lottery tomorrow, what would you buy first?
- What’s better: sweet or savory breakfast foods?
- What’s your most random pet peeve?
- What’s your go-to karaoke song?
- Would you rather show me the last thing you Googled or the last thing you screenshotted?
- If you could invite 5 people (living or dead) to a dinner party, who would you pick?
- Do you have any hot takes or controversial opinions?
- What’s the silliest dad joke you've ever heard?
- What’s the most embarrassing guilty pleasure song on your playlist?
- What’s the corniest pickup line you’ve ever heard?
- If you had to list the top 3 funniest movies of all time, which ones would you pick?

Section 5 of 5:

Tips for Making Conversation with Your Date

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Ask open-ended questions. Open-ended questions invite your date to share their thoughts and feelings about things, rather than just providing a one word answer.^{[4]
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Research source} For example, instead of asking “What’s your favorite song,” try asking “What kind of music do you like to listen to?”
- The first question only requires a simple answer, but the second question gives your date a chance to open up and share more, which can help the conversation flow better.
If you ask too many questions in a row, the conversation can start to feel like a stressful job interview, rather than a fun way to get to know the other person better. To avoid this, matchmaker and dating coach Lauren Sanders recommends narrowing it down to about 4 or 5 questions to start.
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Practice active listening. Active listening shows your date that you're fully engaged and interested in getting to know them better, which is key for a good conversation. It involves things like making eye contact, nodding and reacting to what they’re saying with your facial expressions, and asking thoughtful follow-up questions to delve deeper into topics.^{[5]
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Trustworthy Source

Greater Good in Action
An initiative by UC Berkeley's Greater Good Science Center promoting science-based practices for a meaningful life

Go to source}
- For example, if your date tells you that their favorite travel destination is Italy, don’t just leave it at that and move on to the next topic.
- Follow up with something like, “Wow, I’ve heard Italy is amazing! What do you love about it? Do you usually go to a specific city when you visit?”
- According to dating coach Lisa Shield, it’s essential to take the time to really explore each topic, rather than skipping around from subject to subject. “Really great conversation happens when you take one topic and go deeper with it,” she says.
Most people find it a pretty big turn off if their date goes on and on about themselves, without showing an equal interest in the other person, explains dating coach Judith Gottesman. In fact, she says this is one of the most common complaints she receives from clients after first dates! If you notice that you’ve been monologuing or hogging the conversation for a while, shift your focus to your date and focus on asking them questions about themselves.
“The whole purpose of the first date is to go on a second date,” says matchmaker and dating expert Maria Avgitidis. “It’s not to determine if you’re going to marry this person. It’s just to determine if you’re having fun.” In other words, don’t stress yourself out trying to ask every question to figure out if your date is your soulmate—there’ll be plenty of time for that down the line! “Just let the conversation organically happen,” says Avgitidis.