Funny First Date Questions: The Key to a Night Full of Laughs

Want to have fun on your first date? These funny first date questions will help you get things rolling and hopefully, you’ll have a night’s worth to remember.

“Do you remember your first date?”

This is a very popular question to ask to couple.

Yes, the first date is undeniably important. Victoria Beckham even saved the outfit she wore on her first date with David to pass down to their daughter, Harper.

Unfortunately, most of us are suck in starting conversations. The more attractive your date is, the more you have no idea what to say.

That’s where the list of funny first date questions come in—they’re like a cheat sheet, but totally legal! (And don’t worry, we’ll show you how to use them without offending your date.)

You’ll never run out of things to say.

In this post, you’ll discover the best funny first date questions that will have you both chuckling and who knows, you might just find your other half.

This post is all about funny first date questions that will keep the conversation flowing!

Romantic questions to ask on a first date

Why You Need This Funny First Date Questions List?

Because everybody gets nervous on their first date. And what do people do when they’re nervous? They do stupid things that might ruin the date entirely.

That’s why having these funny first date questions will help you navigate the situation when awkward silence starts to creep in.

The best part is, that you don’t need to pretend you’re a top-notch conversationalist. Just be honest and say, “I find these funny first date questions on the internet. Why don’t we give it a try and see how we feel about it?”

10 of 10 I’m sure you’re date will agree.

Additionally, this also shows that you put the work into the date.

That’s a good first impression.

How to Use This Funny First Date Questions List?

This list isn’t just about funny first date questions. You can also find different types of questions such as conversation starter questions, getting to know you questions dating, romantic questions to ask on a first date, deep first date questions, spicy questions to ask on a first date, and so on.

In simple words: you have plenty of choice.

However, to benefit from this list, you must use it the right way. Here are some practical tips for you:

1. Let your date choose which category he wants to dive in.

Send the link to this article, and let your date choose which categories (or even questions) he wants to answer.

This will make him feel in control and avoid asking questions that make your date uncomfortable.

2. Listen to your date’s answer.

This list isn’t a to-do list where you must ask all the questions.

The point of these funny first date questions is to help you break the ice.

So, when your date chooses his categories or questions, listen to his answer. Look at him (not in the creepy way please!), pause when he finishes his answer, and say, “That’s interesting. Tell me more about that (or you can ask follow-up questions).”

People love to talk about themselves, so asking additional questions will keep the conversation going.

Oh, do I have to mention this: put your phone on silent.

3. Don’t make it an interrogation.

Once your date is done answering a question, it’s your turn.

Make sure you also take your turn to avoid giving the impression that your date is in a job interview. Or even worse: interrogation.

Anyway, some of the categories mention “questions for boyfriend.” You can also use it to ask your date (not necessarily have to be a ‘boyfriend’).

Plus, if you date someone you already know for quite some time, maybe asking spicy questions will be fun.

If you’re meeting a stranger from a dating app, keep the questions light and appropriate—at least for now.

Questions to Ask Before Dating

The worst thing you can do before going on a date is not knowing what you expect.

Yes, a photo with too much filter can be a problem, but also not having the slightest clue about your date’s personality.

That’s why you can ask these questions before dating (also make your chat fun).

Here are some ideas for you:

What’s your perfect first date—romantic dinner, spontaneous adventure, or awkward small talk over coffee?
What’s one thing a date could do that would immediately impress you? (Bonus points if I can actually pull it off.)
First-date etiquette check: Do we split the bill, take turns, or let fate (aka the waiter) decide?
What’s the weirdest thing you’ve seen or heard on a first date? Just so I know what NOT to do.
If we could fast-forward to the end of the night, what would be the best possible outcome? (Hug, high five, planning date #2, or pretending we never met?)
What’s your take on texting after the date—instant reply, wait three days, or disappear into the void?
What’s the most embarrassing thing you’ve ever done on a date (so I can try to top it)?
Would you rather have unlimited tacos for life or an unlimited travel budget—but you can never eat tacos again?
If your life was a rom-com, what’s the most awkward meet-cute moment you could imagine?
What’s your ultimate “nope, I’m out” moment on a first date?

Pick one or two questions from this list, and you’ll get a glimpse of your date’s personality from their answer.

First Date Questions for Him

Now that you’re on your first date, it’s time to have fun.

Here are 10 first date questions for your guy:

If you could have a superpower just for first dates, what would it be? (Mind reading? Endless charm? The ability to escape bad dates undetected?)
If your life had a theme song that played every time you walked into a room, what would it be?
What’s one thing you secretly judge people for on a first date?
Would you rather forget your wallet on a first date or accidentally call me by your ex’s name?
What’s the weirdest food combo you swear by? (And should I be scared?)
Be honest—did you actually read my dating profile, or just swipe based on my pictures?
What’s your most unpopular opinion? (Let’s see if I can handle it.)
If you could switch lives with a movie character for a day, who would it be and why?
Would you rather be trapped in a rom-com or an action movie? (And how do you think you’d survive?)
If you could be any Avenger, who would you pick and why?

Personal questions to ask on a first date

Conversation Starter Questions

People say first impressions last forever.

Once you meet your date in person, say thank you for coming. This is classic but never fails good first impression.

But, what then?

We got you covered.

Here are 10 easy conversation starters to kick things off:

So, how was your day before this? Anything interesting happens?
Shall we eat real food or just pretend snacks are enough?
I was looking forward to this! Have you been to this place before?
I always think first impressions are funny—what was your first impression of me?
If you had to describe yourself with just one word, what would it be? I’ll go first… [insert your word]. Your turn!
You seem like someone who has good taste—what’s a show or movie I absolutely need to watch?
I love trying new things. Is there anything you’ve been wanting to do but haven’t yet?
I need to settle a debate—do you text with proper punctuation, or are you more of a “lol no caps” person?
If I handed you a plane ticket right now to anywhere in the world, where are you going? ✈️
If we had to pick a theme song for this date, what would it be? 🎶

Funny First Date Questions to Ask a Girl

Humor is the thing that makes everything better, especially a date.

So pick something from these funny first date questions to ask a girl and have some LOL:

If we were in a zombie apocalypse right now, what’s your survival plan?
What’s the most ridiculous thing you’ve ever Googled?
If you could switch lives with a cartoon character for a day, who would it be?
Would you rather have a rewind button or a pause button for life?
What’s the weirdest thing you believed as a kid?
What’s the most dramatic way you’ve ever quit something?
If your life was a movie, what would the title be?
If animals could talk, which one do you think would be the biggest gossip?
What’s something completely useless that you’re really good at?
If you had a personal theme song that played every time you entered a room, what would it be?

Funny First Date Questions to Ask a Man

Want to see his goofy side?

These funny questions to ask your boyfriend (or date) will do the trick!

Here are 10 funny first date questions to ask a man:

If you had to describe yourself using only one emoji, which one would it be? 🤔
Be honest—have you ever sent a text and then immediately regretted it? What was it? 😆
If you had to compete in an Olympic sport (with no training), which one would you choose?
If we had to do a trust fall right now, would you catch me, or would we both end up on the floor?
What’s one movie that everyone loves but you secretly can’t stand?
You just won an unlimited supply of one snack—what’s it gonna be?
What’s the most dramatic way you’ve ever tried to get out of a bad situation?
If I let you rename me for the night, what name would you pick?
If we got lost in the wilderness, would you be the survival expert or the first one to panic?
What’s the weirdest thing you’ve ever done on a dare?

Getting to Know You Questions Dating

Once you get your drink on the table, some snacks, and have some laughs, it’s time to get to know each other.

Here are 10 “Getting to Know You” questions for dating:

If you could live anywhere in the world for a year, where would it be?
What’s a small thing that instantly makes your day better?
Do you believe in love at first sight, or is it more like “let’s see how this goes”?
What’s one hobby or skill you’ve always wanted to learn?
If someone made a movie about your life, what genre would it be?
If you had a free day with no responsibilities, how would you spend it?
What’s something people always assume about you, but it’s totally wrong?
What’s a childhood dream you never gave up on?
What’s your guilty pleasure song that you secretly love?
What’s the best compliment someone has ever given you?

Romantic Questions to Ask on a First Date

You will need these romantic questions after you feel the chemistry with your date.

Or if you want to see if your date has the same ideas about what romantic is in a relationship.

Here are 10 romantic questions to ask on a first date:

What’s the most romantic thing someone has ever done for you?
Do you believe in soulmates, or do you think love is about timing and effort?
What’s your idea of the perfect date night?
What’s one quality in a partner that makes you feel truly loved?
What’s your favorite love story—real or fictional?
If we were to take a spontaneous romantic getaway, where would we go?
How do you usually show affection—words, actions, gifts, or something else?
What’s one thing that instantly makes you feel connected to someone?
How do you know when you’re truly falling for someone?
What does “happily ever after” look like to you?

Deep First Date Questions to Ask a Woman

Sometimes chemistry sparks on the first date and you want to move past small talk.

These serious dating questions will help you learn about your woman on a deeper level.

Here are 10 deep first date questions to ask a woman:

What’s one experience in your life that shaped who you are today?
If you could give your younger self one piece of advice, what would it be?
What’s something you’re really passionate about, and why does it matter to you?
What’s your idea of true happiness?
What’s a lesson you learned the hard way, but are grateful for now?
How do you usually handle challenges or setbacks in life?
What’s a belief or value that you’ll never compromise on?
When do you feel most like yourself?
What’s one thing you hope to achieve in the next five years?
What’s the most important thing you look for in a relationship?

Deep First Date Questions to Ask a Guy

Someone once told me that a man is a simple creature—give him good sex and a full belly, and everything will be just fine.

Or is he?

Why not find out for yourself by asking deep first-date questions to your new guy?

Here are some thought-provoking questions to inspire you. But be warned—you might discover that men aren’t as simple as they claim!

What motivates you to get up in the morning and keep pushing forward?
What’s a moment in your life that completely shifted how you see the world?
How do you define success, and has that definition changed over time?
What kind of legacy do you want to leave behind?
Who has had the biggest influence on the person you are today?
If you could master any skill instantly, what would it be and why?
What do you think is the most important quality in a life partner?
When was the last time you took a big risk, and how did it turn out?
How do you handle conflicts in relationships—whether romantic, family, or friendships?
What’s one thing you’re still trying to figure out about yourself?

Spicy Questions to Ask on a First Date

Please tell me this is your favorite part so I don’t feel alone.

Hahaha…

We all love asking spicy questions about our date.

Just a little heads-up—this question could either make things more interesting or totally backfire.

Are you in?

Here are 10 spicy questions to ask your boyfriend or date:

What’s your idea of the perfect kiss?
Are you more of a slow-burn romance or instant chemistry type?
What’s the most daring thing you’ve ever done in the name of attraction?
Do you believe in love at first sight, or does it take a little teasing first?
What’s the most unexpected thing that turns you on?
What’s one flirty move that never fails to work on you?
If we were playing truth or dare right now, what’s the boldest dare you’d accept?
What’s a guilty pleasure that would surprise people about you?
Do you like to take the lead in romance, or do you enjoy a little chase?
What’s one thing you find irresistibly attractive in a person?

Risky Questions To Ask Your Boyfriend

Curiosity can be a double-edged sword.

Sometimes, the truth sets you free, and other times, it stings.

But for someone like me, the feeling of not knowing is worse than facing the truth head-on.

So, if you’re feeling bold…

Here are some risky questions to ask your boyfriend (or dates):

Have you ever had a moment where you questioned our relationship?
What’s something you’ve never told me because you’re afraid of how I’d react?
If your ex wanted you back right now, what would you do?
What’s a fantasy you’ve never told anyone about?
Have you ever felt tempted in a relationship—even if you didn’t act on it?
What’s the biggest lie you’ve ever told in a relationship?
If we had a huge fight, what’s something I could say that would actually hurt you?
What’s one thing you’d change about me if you could?
If we broke up tomorrow, what’s something you’d miss the most (and least) about me?
Do you believe we’re truly meant to be together, or are we just figuring things out as we go?

Random Questions to Ask Your Boyfriend (or Dates)

Do all your dates feel the same?

You know—the same questions, polite laughter, and a goodbye at the end.

Maybe it’s time to shake things up and go off-script!

Let’s shake things up with some fun and random questions!

If you could relive any day of your life, which one would it be and why?
What’s the weirdest food combo you actually love?
If your life had a theme song, what would it be?
What’s one thing you’ve always wanted to try but never had the chance?
If you had to pick a new career just for fun, what would it be?
What’s the most spontaneous thing you’ve ever done?
If you could swap lives with a celebrity for a day, who would it be?
What’s one small thing that instantly makes you happy?
If you could have dinner with any historical figure, who would it be and what would you ask them?
What’s the most ridiculous thing you’ve ever Googled?

Hypothetical Questions For Boyfriend (or Dates)

For me, hanging out with people full of imagination will make your day better.

I don’t like a dull person whose you already know what they’ll say before they say a thing (if you know, you know).

Asking hypothetical questions to your plus-one will show you a lot of his personality. Let’s find out!

If you woke up tomorrow with a superpower, what would it be and how would you use it?
If we had to go on the run and assume new identities, what names would we pick?
If money wasn’t an issue, what crazy adventure would you plan for us?
If you could live in any fictional world for a year, where would you go?
If you had to swap lives with one of your friends for a week, who would it be and why?
If aliens landed tomorrow and offered you a one-way ticket to explore the universe, would you take it?
If you could relive one day of your life (but not change anything), which one would it be?
If we could only communicate using movie quotes, which movie would you pick for us?
If you had to cook me a meal to impress me, what would you make?
If you could bring back one extinct animal to have as a pet, which one would you choose?

How to Keep the Conversation Going?

These funny first date questions should give you a good start on your date.

Unfortunately, starting a conversation and keeping a conversation going are two different things.

Here are some tips for you to keep the energy flowing naturally.

Avoid yes/no questions—ask open-ended ones instead.
Share your own experience.
Give compliments and ask follow-up questions to show you’re really listening.

If you feel like your date isn’t having a good time despite your efforts to keep things fun, be honest and ask something like, “You don’t seem to be enjoying our time together. Is there anything I can do to make you feel more comfortable?”

Whatever the answer is, don’t take it personally.

If your date wants to cut the date short, allow her to. Say thank you and call it a day.

Pick Your First Question and See Where It Leads!

Now that you have a list of funny first date questions, you should never run out of conversation ideas.

It’s time to put them to the test!

You might just be surprised at the stories, secrets, and smiles waiting on the other side.

Go out there and meet new people in real life.

Good luck!