First Date Questions: 189 Questions to Ask on a First Date

Asking the right questions on a first date is so important because it’s how you get to know someone on a deeper level. After all, they don’t call it the talking stage of the relationship for nothing. Expressing curiosity and interest in a person through personal questions is also how you show someone you’re interested in them. It seems so obvious but people on dates often don’t do this enough or, even worse, monopolize the conversation by talking about themselves and their own interests too much.

It’s not so much about the questions but about what the answers achieve in a budding relationship. The best first date questions help you establish what you have in common and whether you feel natural chemistry when you’re in an active conversation. By getting to know each other, you also start to build the foundations of trust and connection, leading to a more natural and intimate way of interacting.   

But there are also the right kinds of things to ask on a first date. For instance, “What’s your favorite color?” isn’t the best idea to get to know someone. You should ask them funny first date questions, questions about the passions and interests that make their life full, random questions they wouldn’t typically expect, questions that playfully flirt with them and questions that make them stop and think. Questions that manifest exciting new conversational avenues to explore, while still respecting their initial boundaries. 

In this way, the best questions on your opening date shouldn’t just be digging for information but also expressing interest, creating an experience and entertaining them. If you’re stuck on what’s the best way to approach this, these 189 questions can help get you started and give you some inspiration to think of your own, in the moment.    

First date conversation starters

A conversation starter is how you get the ball rolling on a date. These are often very general questions on a first date that are designed to be somewhat bland and innocuous, as people on first dates often don’t know each other very well yet.

These ice breaker questions for dating help gently diffuse some of the nerves either of you may be feeling and start the process of getting to know each other better. It’s not so much about what their answer is but what that answer tells you about the person, what to ask next and presents different places you can take a growing conversation.

Just because conversation starters are broad doesn’t mean they have to be boring, so avoid asking about their job or their opinion on the weather and try some of these.   

1. What’s your favorite way to spend a Sunday?
2. Do you enjoy cooking or prefer eating out?
3. What kind of music do you listen to the most?
4. Do you like traveling or do you prefer staying local?
5. What’s your favorite type of movie or series?
6. Do you enjoy outdoor activities like hiking or biking?
7. What’s your go-to comfort food?
8. Do you prefer mornings or evenings?
9. What’s a hobby you enjoy in your free time?
10. What’s the last book or article you read that you liked?
11. Where did you grow up and did you like it?
12. What was the highlight of your week so far?
13. Seen any good movies or TV shows lately?
14. What’s the most interesting thing you’ve learned recently?
15. Are you working on any personal projects?
16. What kind of music have you been listening to?
17. How has your day been leading up to this?

Questions to ask a guy on a first date

Asking a man questions on a first date can be a bit different from when you’re dating a woman. For one, guys might not be as social as women. Studies have shown that men tend to be less outgoing and enthusiastic in conversation than women,¹ which can make them a little more challenging to draw out of their shells. It’s best to start off with broader questions at first until you build a friendly rapport. Men sometimes also tend to avoid discussing strongly emotional topics while preferring more exterior topics like current events, their personal history, interests and pop culture.² So, the right questions to ask a guy are essentially the same as with women.

1. Do you enjoy doing sports?
2. What’s your go-to drink order?
3. What’s a place in the city/town you love visiting?
4. Do you prefer nights out or quiet nights in?
5. What do you usually do on weekends?
6. Do you like playing or watching video games?
7. What’s your favorite way to relax after work?
8. Are you more of a dog or cat person?
9. What’s a small thing that makes you really happy?
10. Do you enjoy surprises?
11. What’s something you could talk about for hours?
12. What’s the most adventurous thing you’ve ever done?
13. What’s a challenge you’ve overcome that you’re proud of?
14. Who were your heroes growing up?
15. What are you competitive about?
16. What’s a skill you’ve always wanted to learn?
17. How do you and your best friends spend your time together?

Questions to ask a girl on a first date

Women, on the other hand, tend to be a bit more outgoing and agreeable in conversation. Generally, the questions you ask a girl can be deeper or more familiar in tone from quite early on in the date. But this also means that some women give less obvious cues when a question or topic is something they don’t enjoy discussing, to better maintain social harmony.

Pay attention to her body language when you ask a girl questions on a first date. If she begins to close her posture, maintains less eye contact or stops giving positive cues while you talk, like gently nodding along, it could be a sign to pivot the conversation into a different direction with another question.

In terms of first date topics, try to remember that women can often have higher boundaries on first dates. So, avoid asking questions that might feel you’re trying to get very sensitive information from them. Stick to discussing passions and aspects of each other’s personalities until you build trust.

1. What’s something that always makes you laugh, no matter what?
2. What’s the best trip you’ve ever been on?
3. Who in your life do you feel closest to?
4. What’s a creative outlet you enjoy?
5. What’s the best compliment you’ve ever received?
6. What’s a quality you really admire in other people?
7. What little luxury do you love to treat yourself to?
8. What’s your favorite kind of dessert?
9. Do you like trying out new restaurants or sticking to favorites?
10. What’s your ideal way to spend a Saturday?
11. Do you enjoy concerts or live shows?
12. What’s your favorite type of cuisine?
13. Do you prefer spontaneous adventures or planned activities?
14. What’s your go-to karaoke song?
15. Do you like staying in or going out more?
16. What’s the most fun trip you’ve ever been on?
17. Do you enjoy art, museums, or creative spaces?

Good first date questions tend to be ones you explore a bit later on in the date. Once the conversation has a bit of momentum, you’re more comfortable with each other and you’ve begun to gauge your date’s general level of openness and the topics that spark their interest.

While these are still essentially getting-to-know-you types of questions, they should probe a little deeper into their interests and how they fill their lives. The right question to ask on a first date shouldn’t just be about gathering information on each other, though. It should also excite your date and make them think of interesting things they perhaps haven’t put into words before. In short, they should also be entertaining or engaging.  We’ve gathered a few examples to use, but you can also adapt them based on how your date is going and what questions have gotten the most animated responses.

1. What do you like spending money on?
2. What’s something you’re genuinely excited about in your life right now?
3. How do you like to spend your time when you’re not working?
4. What’s the best meal you’ve had recently?
5. Are you a morning person or a night owl?
6. What’s a skill you’d love to master?
7. If you could travel anywhere tomorrow, where would you go?
8. What’s a small thing that can make your day better?
9. What’s your favorite holiday tradition?
10. Do you like to cook? If so, what’s your signature dish?
11. What’s the best trip you’ve taken recently?
12. What’s a simple thing that always makes your day better?
13. Do you enjoy coffee dates or dinner dates more?
14. What’s your favorite local spot to hang out?
15. Do you like pets?
16. What’s a fun fact about you most people don’t know?
17. Do you prefer the beach or the mountains?
18. What’s the last movie you really enjoyed?

Silly first date questions

Never forget to enjoy yourself while dating by also asking funny and silly questions on the first date. While romance is the ultimate goal, looking for the right person should also offer you new experiences and be an enjoyable journey in and of itself. If you stay too focused on the destination, you may start to become frustrated or disenchanted with the dating process and start looking at it as a chore rather than an enjoyable outlet.

Throwing in some fun questions to ask on a first date can help lighten the mood if things feel a bit quiet, creates a tone of playful banter and tacitly give them permission to be a little more silly themselves. A University of Oxford study found that humor was a unique social tool for getting people to open up and develop intimacy more readily.³ And having shared humor as a couple has also been shown to be strongly connected to relationship satisfaction.⁴

1. What’s the most embarrassing song you listen to?
2.  Do you think pineapple belongs on pizza?
3. What’s the worst date you’ve ever been on? (Let’s hope it’s not this one!)
4. What’s a weird food combination you secretly love?
5. If you could have a superpower, what would it be?
6. Is a hotdog a sandwich? I need to know your stance on this.
7. What is the silliest thing you have an emotional attachment to?
8. What was the weirdest thing about the town/neighborhood you grew up in? 
9. Do you prefer going out to restaurants or just takeout and TV in your pajamas?
10. What was the story behind your worst first date? And please don’t say it’s me.
11. What TV or movie universe have you always secretly wanted to live in?
12. If you’d never met me before, what would you guess my name and occupation is?
13. What song lyrics did you get wrong for years until someone noticed?
14. What’s something that always makes you cringe?
15. What’s a secret talent you have but never show to anyone?
16. What’s the craziest lie you ever came up with as a child?
17. What’s one fashion trend you wish would come back?

Serious first date questions

At some points during your date, you may find that the tone of the conversation becomes a little less excited or humorous at times. This doesn’t mean you’re boring them. Conversations naturally have peaks and valleys as you explore different topics and start expressing new ranges of emotion. This is the perfect time to think of a deep question to ask them, which focuses less on creating light banter and more on exploring the deeper notions of their personality and how they see the world.

Deep first date questions have a couple of functions. Firstly, they let you more subtly establish whether you have a deeper compatibility that goes beyond chemistry and attraction and speaks more to how this person may relate to you and behave in a long-term relationship. Secondly, by asking more serious questions sometimes, it signals that you aren’t superficial but instead want to get to know them fully.    

1. What do you value most in a friendship?
2. Do you believe in long-term commitment?
3. How important is family in your life?
4. Do you see yourself settling in this city/town long-term?
5. What’s something you’re currently working on improving about yourself?
6. How do you usually handle stress?
7. What’s your definition of success?
8. Do you see yourself wanting children in the future?
9. How important is work-life balance to you?
10. What’s one life lesson that has stuck with you?
11. Do you want to get married in the future?
12. What are you most proud of that isn’t related to your career?
13. What does “a life well-lived” mean to you?
14. What’s a lesson you had to learn the hard way?
15. What’s something you wish more people understood about you?
16. When do you feel most like your authentic self?
17. What do you value most in your friendships?
18. What are you currently working on in your personal growth? 

Intriguing first date questions

If you’ve been actively dating for a while, it can be easy to slip into a certain conversational routine on dates. This can become mundane, making you less excited and present during interactions. If you only date half-heartedly, your date will be able to pick up on it either from your tone or non-verbal cues. Intriguing and interesting first-date questions tend to break away from our social routines and ask more thought-provoking questions.

They shake the conversation up a bit and take it in new directions. Like serious date questions, exploring interesting questions to ask during your date can give you a greater perspective of the other person and how their personality is organized. It also has the benefit of making you seem more intriguing by extension, because it shows that your mind works a bit differently and more deeply than others. This can help your date with them stand out amongst other possible singles they’ve been interacting with.  

1. What’s a passion project you’d love to start?
2. Do you believe people meet for a reason or by chance?
3. What’s something you’ve always wanted to learn?
4. If you could live anywhere in the world, where would it be?
5. What’s an experience that changed how you see the world?
6. Do you think dreams have hidden meanings?
7. What’s your take on the idea of soulmates?
8. If you could know one thing about your future, what would it be?
9. What’s the most inspiring story you’ve ever heard?
10. Do you think people can truly change?
11. What’s a risk you took that really paid off?
12. What’s something you’ve changed your mind about recently?
13. What’s the best piece of advice you’ve ever received?
14. If you could ask your future self one question, what would it be?
15. What book or movie has had a big impact on you?
16. What’s an unpopular opinion you stand by?
17. What’s a story you love telling about yourself?

Romantic questions aren’t strictly flirty – although they do implicitly indicate a certain romantic interest and cultivate a more intimate mood – but rather explore how your date interprets romance to help you see if you’re compatible and so that you can relate to them better on future dates. It also shows that you’re not looking for something casual when dating. These first date questions can include what kind of dates they prefer to go on, their perspective on love and companionship and how they’ve approached relationships.

Such questions allow you to really get to the heart of the matter by exploring what it’d functionally be like if you developed a relationship with this person. Try to remember this is only your first date, though. Make sure your romantic questions don’t sound like you’re vetting them and try to make them broader and more restrained, like you’re just casually finding out more about them, or it may come across as inappropriate.

1. What’s your idea of the perfect date night?
2. Do you enjoy small romantic gestures?
3. What makes you feel most appreciated in a relationship?
4. Do you like surprises, or do you prefer knowing plans in advance?
5. What’s the most romantic movie you’ve ever seen?
6. Do you believe in love at first sight?
7. What’s a simple way someone can make you smile?
8. What’s your favorite romantic song?
9. What makes you feel most cared for?
10. Do you think romance should be simple or grand?
11. Do you consider yourself a romantic person?
12. What’s the most romantic gesture someone could do for you?
13. What do you think is the most important part of a relationship?
14. What’s your love language?
15. Do you believe in love at first sight? Or “love at first vibe”?
16. Describe a perfect, romantic evening.
17. What’s a song that always makes you think about love?

Flirty questions to ask on a first date

Flirting is generally encouraged during a date, in appropriate measures. However, flirting on the first date can feel more intimidating because you don’t know the person well yet and you may be nervous that if your attempt comes out clumsily, it may end up having the opposite effect.

These are just the typical nerves people get on a first date when they overthink things. If you’re not ready to flirt directly yet, you can take the more subtle route of asking flirty questions on your first date to signal your interest. Unlike romantic questions, flirty ones are less direct and more playful. It’s more about trying to give the interaction a certain exciting energy so that it starts to feel more like a proper date rather than a dry interview dynamic, which many first dates default to.        

1. What’s the most fun way to spend a date?
2. Do you like compliments, or do they make you shy?
3. What’s a small thing someone can do to win you over?
4. Do you like playful teasing?
5. What’s the most fun you’ve had on a date?
6. Do you like public displays of affection?
7. What’s a trait you find really attractive?
8. Do you like surprises when dating?
9. What’s the best compliment you’ve ever received?
10. Do you prefer cozy dates or adventurous ones?
11. So, what did you think when you first saw me?
12. What’s your idea of a perfect second date?
13. What’s something you find attractive that might surprise people?
14. Are you always this charming or am I just getting special treatment?
15. What’s your biggest turn-on?
16. Besides your great smile, what’s your best feature?
17.  How would you describe your typical type?

Unpredictable first date questions

Unpredictable and quirky questions on a first date tend to be more abstract and unique. They help change things up in the conversation if it’s stalled or you’re stuck on one of those conversational tracks that are just somewhat boring and predictable first date topics, like work and family.

The random question you ask should, preferably, be one they’ve never really been asked before, so they’re compelled to really stop and think about the answer. This often forces people to break from their typical communication style and reveal more deeply personal aspects about themselves,⁵ making dates feel more intimate and rewarding.  

It’s also been shown that deviating slightly and playfully from traditional interpersonal scripts on dates can make you seem more creative and confident, and signal higher social value. However, it’s important not to go too random with your questions or it can conversely end up manifesting feelings of discomfort and rejection.⁶ Here are some ideas:

1. If you could instantly master a skill, what would it be?
2. What’s the strangest food you’ve ever tried?
3. Would you rather travel to the future or the past?
4. If you could direct a movie, what would it be about?
5. What’s the most spontaneous thing you’ve ever done?
6. If you could switch lives with someone for a day, who would it be?
7. What’s the funniest thing that’s happened to you recently?
8. If you could teleport anywhere right now, where would you go?
9. Do you believe in fate or coincidence?
10. What’s the quirkiest thing about you?
11. If you could have any animal as a pet, mythical or real, what would it be?
12. What’s the most useful thing you own?
13. What’s a conspiracy theory you secretly find a little believable?
14. If you had a personal theme song, what would it be?
15. Which fictional character do you relate to the most?
16. What’s a weird fact that you know?
17. If you had to live in a different historical period, which one would you choose?

Questions to ask on a dating app before the first date

It’s no secret that conversations over dating apps can sometimes be a bit more challenging than face-to-face because you’re not able to see the person. It not only makes it more challenging to relate to each other but some people online also find it easier to dehumanize a two-dimensional face and some text on a screen.⁷

So, the best questions to ask on a dating app are ones that immediately make you stand out from the typical messages they receive. The goal is to catch their attention and inspire curiosity. You should also try to gently push the idea of dating early on by being a bit flirty and romantic to show you’re really invested in the online dating process. On the other hand, a funny question can make them feel more comfortable with you and empathize more directly with the person on the other side of the screen.

1. What made you like my profile?
2. Do you prefer texting, calling, or video chatting before meeting?
3. What’s your idea of a perfect first date?
4. What’s something unique about you not in your profile?
5. Do you usually make the first move on dating apps?
6. What’s your favorite way to relax after work?
7. Do you enjoy weekend getaways or staying home?
8. What’s your favorite kind of food to try on a date?
9. What’s the most fun conversation you’ve had on a dating app?
10. Do you prefer coffee dates or evening dinners for a first meet?
11. What’s one thing on your profile that you’re hoping people ask you about?
12. What’s the most spontaneous thing you’ve done recently?
13. If you could plan our ideal first date, what would we be doing?
14. What’s your communication style like? Big texter or more of a phone call person?
15. What’s a simple pleasure that you really enjoy?
16. Sum up your personality in three emojis. Go!
17. What’s your go-to “bad day” cure?

What are the best tips for asking a question on a first date?

While these first date question examples can be a helpful starting off point, it’s also good for the questions to flow naturally from what you’re talking about. Here are some first date tips when it comes to coming up with the right questions.    

• Encourage exchange – Ask open-ended questions that lead to other conversational topics.
• Mix it up – Ask them a variety of different types of questions to see what dynamic works best for them.
• Respect their boundaries – Don’t ask questions that are too personal or inappropriate for someone you’re just getting to know.
• Listen actively – It’s not just about the questions but about taking their response on board so you can build on it and figure out more personalized questions.
• Don’t pepper them – Ask questions in moderation or you may end up making them feel like they’re being interrogated.
• Keep it light – The main aim of a first date is to have fun. Avoid things that may make them reflect too much on their life, consider regrets or are emotional sore points for them. 
• Try to stand out – They may be actively dating at that point, so by asking more original and compelling questions than other dates, you can quickly distinguish yourself from other possible options and create a more unique experience.

What to talk about on a first date?

The right things to talk about on a first date should feel natural, light-hearted and help you feel the other person out without making it feel like an interview. Let’s look at some tried and tested first date conversation topics and questions while exploring those first date topics.

How to prepare for a first date?

Although a first date is meant to feel light and easy, it’s completely natural to feel a little nervous. A bit of preparation can help ease those jitters and boost your confidence. Here are some gentle tips to help you feel more relaxed:

• Consider your dating goals and whether this date is the kind of thing you’re looking for right now.
• Think up some interesting first date questions beforehand. Have some backup ones too, in case the conversation wanes.
• Confirm the date and the time you’re meeting with them on the day to check in and avoid any confusion.
• Do a full hygiene run-down to make a great first impression. Things like washing your hair, clipping your nails, brushing your teeth, making sure what you’re wearing is fresh, shaving and even cleaning your car.
• Try to get a good night’s sleep beforehand so you’re not tired or in a poor mood on the date.
• Plan an outfit that typically makes you feel comfortable, fashionable and attractive.
• If you met through online dating or it’s a blind date, check out their socials to get a better idea of them and some clues about what types of questions to ask.
• Make sure your date can see you put effort into looking good for them without making it seem like you’re trying too hard.
• Avoid any negative self-talk. Even if you’ve been having some bad dates recently, it only takes one good one to make all the difference.
• Don’t overthink the date or first date questions. Simply look at it as a new experience, good or bad.    

How to be less awkward on a first date?

Even though first dates can sometimes feel a little intimidating, there are simple ways to ease the pressure and show up as your most natural, comfortable self.

• You can avoid being awkward on a first date by not having too many expectations going in. Try to go with the natural flow of the date.
• Listen to some music or talk to a friend beforehand just to keep you relaxed, upbeat and confident for the date.
• Don’t create initial distance simply to be respectful. Pick the seat next to or adjacent to them and avoid loud venues that get in the way of hearing each other properly.
• Have something that can occupy you both and fill the space during lulls in the conversation. Like for instance, a scenic view on a walk, doing an activity together or attending a museum.
• Leave any elephants outside the room. If you say something awkward or one of your first date questions comes out weirdly, don’t act oblivious. Own it and show that you’re self-aware and can laugh at yourself.
• Always be yourself. This may sound obvious, but the more you place yourself in a position of wanting to be the ideal date, the more tension it’s going to create because it won’t feel natural or sincere.

What are the best activities for a first date?

Any kind of activity that’s low-pressure, you’d both enjoy and would feel comfortable doing. Beyond playful or deep first date questions and picking the right conversation topics, what you do on the date can affect how they feel about your connection. Here are some first date ideas that might work for you.

What should you wear to a first date?

A study in the Family and Consumer Sciences Research Journal confirmed you can significantly influence how attractive you appear through your clothing.⁸ So, those first date looks are as important as first date questions when it comes to making a strong impression.

Other studies have found that color plays an important role. Both men and women showed a strong attraction to red and black.⁹ However, the color blue elicited the highest degree of comfort in situations.¹⁰ So, it’s up to you to decide which aesthetic tone you’d like to strike. Bold or familiar. But one thing most studies agree on is that you should never wear yellow on a first date.¹¹

What questions should you be asking yourself before going on a first date?

You should always date for yourself, so it’s also important to ask yourself questions about your dating goals and what you hope to get out of it. Here are a few questions to ask yourself before dating.

• Am I dating for the right reasons or because I think it will solve other problems in my life?
• What kind of partner would be most compatible with me?
• What do I want to get out of dating? Some new experiences, meet new people or find a long-term relationship?
• How much time and money am I willing to commit to dating life?
• What are my green flags and red flags?
• How can I help this turn out more positively than past relationships? 

Self-care and respecting your emotions are vital for a healthy dating life. So those true first date questions should really be to yourself and you should have a solid answer to them before you start dating and stronger emotions start becoming involved.

What questions should you avoid asking on a first date?

It’s always prudent to avoid anything that might offend someone, is too familiar or crosses a common social boundary. Here are a few examples of some first date questions to steer clear of.

• Why are you still single? – This implies that being single amounts to a life failure (which is ironic, coming from someone who’s also single) or that there’s something specific they do to frighten partners off.
• How much money do you make? – This tells them you’re either dating to improve your financial position or that you shallowly base the value of people on their earning potential.
• How many people have you slept with? – Firstly, it’s just none of your business. Secondly, it comes across as very intrusive on a first date and gives the impression that you would judge them based on the number.

What questions to ask after a first date?

Doing a little mental inventory post-date is a great way to get a clearer idea of how the date went and how you feel about things. Here are some post-first-date questions you should ask yourself.

• Did we click? – You may have shared some interesting stories and even had a few laughs but it’s important to ask yourself whether it felt like there was real chemistry or if it was simply a pleasant interaction.
• How did they make me feel? – Did you feel comfortable around them or somewhat on edge the whole time? As the date progressed, did you feel or act on an impulse to make physical contact with them or reduce your proximity?
• How did they make me act? – It’s also important to look at what side of you they bring out. Do you feel like you’re your best self around them or do they perhaps appeal to certain negative aspects of your personality and dating history?
• Do I feel attractive around them? – Superficiality aside, if they don’t make you feel wanted and special in some way, wait for someone better to come along.

When to ask for a second date?

The general opinion is that it doesn’t hurt to ask as soon as possible. The popular dating blogger and influencer Stephanie Daily surveyed her followers and found that 73% of respondents found 1-2 days before asking for a second date to be ideal. By day 3, that number had dropped to 18%.¹²

Asking sooner rather than later makes sense when you consider the modern dating scene. It’s not unusual to already discuss the notion of a second date while you’re on your first, if it’s going well. You probably sent them a message (or you should) shortly after the date to thank them for meeting up. Their response will already give you some idea of how well it went. And if you’ve been keeping up semi-regular contact with them online since the date, that likely means they’re still interested in meeting up. You just haven’t made solid plans yet. So it’s better to strike while the iron is hot or they may think you’re not interested and move on.