While being polite and listening well is important on a first date, being funny also carries a fair amount of weight. Having some funny first date questions to help break the ice and fill any awkward silences can set the tone for the date and help you secure a second one!
Whether you’re naturally funny but get flustered under the pressure of a first date, or you struggle to think of witty remarks and one-liners on the spot, we’ve dusted off the old joke book to find some of the best funny questions to ask your date to keep things flowing and help you get to know each other.
In This Guide:
- 60 Funny First Date Questions to Break the Ice
- Why We Love Funny People: The Psychology of Humour
- FAQs

60 Funny First Date Questions to Break the Ice
First dates are hard, so to take the stress out of things, here are some of our best funny first date conversation starters to ask when the conversation lulls or when you want to keep the mood light and fun.
Some of these questions are funny in and of themselves, while others are the perfect opportunity to share funny stories or have a giggle together at the answer.
- What’s more likely to exist: aliens or ghosts?
- If your pet was having a game night with friends, what would they say about you?
- What’s your Hogwarts house and why?
- Which comedy actor would play you in a movie about your life?
- What’s your go-to karaoke song?
- What’s the weirdest thing you’ve eaten?
- What’s the most embarrassing song on your playlist?
- Do you think it’s ok to pee in the shower?
- Do you have any real-life superpowers?
- What 5 things would you take with you in a zombie apocalypse?
- What’s a lie you were told as a kid that you believed for too long?
- What’s the craziest thing you’ve done on a date?
- Would you rather fight a horse-sized duck or 100 duck-sized horses?
- What was your embarrassing childhood nickname?
- What’s the cheesiest pickup line you’ve ever used/heard?
- What’s the funniest question you’ve been asked on a date?
- If you had to be on a reality TV show, which one would it be?
- What would you think my name was if you didn’t know it?
- Have you ever peed in a public pool?
- Have you ever been injured during sex?
- Are you a big spoon or a little spoon?
- What is a weird smell you love that other people don’t?
- Would you rather be fluent in every language or be able to talk to animals?
- What was your signature childhood prank?
- What’s been your best Halloween costume?
- What’s one thing in your pocket/bag that would make me laugh?
- What song is stuck in your head right now?
- What’s the most socially unacceptable thing you’ve done?
- What’s your worst holiday story?
- If you could have dinner with any fictional character, who would it be and why?
- What are the 3 most ridiculous things you would want in your dream house?
- Who are your top 5 celebrity crushes?
- What’s your version of a girl dinner?
- What’s the most unusual or interesting talent you have?
- What’s the most impulsive thing you’ve ever done?
- Which children’s cartoon character did you have an inappropriate crush on?
- What are you weirdly attracted to?
- If you could have a superpower to make dating easier, what would it be?
- What is the dorkiest thing about you?
- What is the most backhanded compliment you’ve ever received?
- What is the funniest red flag you’ve ignored?
- What’s your go-to dance battle-winning move?
- Were Ross and Rachel on a break?
- What’s your funniest misheard song lyric?
- What’s your worst quality according to astrology that is 100% true about you?
- What kind of drunk are you?
- Which Taylor Swift era are you?
- What’s your go-to depression meal?
- If you had to change my name, what would you change it to?
- If you could start a rumour about yourself, what would it be?
- Who would you pick to write your obituary?
- Which character from The Office are you?
(Bonus question: Is the UK or US “The Office” superior?)
- What’s the most overrated sex position?
- What’s the weirdest thing your roommates have ever caught you doing?
- What do you think your boss tells their friends about you?
- If you were a cocktail, what would you be?
- What was the last thing you Googled?
- What’s the weirdest rumour you’ve ever heard about yourself?
- Have you ever crashed a wedding?
- What’s the weirdest gift you’ve ever received?
10 Interesting First Date Questions About Life
To help avoid your date sounding like an open mic night stand-up session, here are some interesting first date questions to ensure they take you seriously as well!
- What’s a hobby or activity you’re passionate about?
- If you could travel anywhere in the world, where would it be?
- What’s your favourite childhood memory?
- Who has been the biggest influence in your life?
- Do you prefer living in the city, the countryside, or somewhere in between?
- If you could only eat one cuisine for the rest of your life, what would it be?
- Is there a skill you’ve always wanted to learn?
- What’s the most interesting book or film you’ve encountered recently?
- Do you have a favourite holiday or special tradition?
- What’s something on your bucket list you’re excited to try?
10 Romantic Questions for a First Date Conversation
Of course, if you’re trying to start a relationship with your date, you’ll want to balance the humour with some genuine romance and romantic interest! Relax.
We’ve picked 10 of our favourite swoon-worthy questions to keep the vibes right.
- What’s the most romantic gesture you’ve ever experienced or given?
- What’s your idea of a perfect date night?
- Do you believe in love at first sight?
- What’s a romantic movie or book that really resonates with you?
- What’s the most meaningful compliment you’ve received from someone?
- What do you think makes a strong emotional connection between two people?
- What’s your favourite memory of a moment that felt truly magical?
- What’s something small that instantly makes you feel loved?
- If you could plan a dream getaway with someone special, where would you go?
- What’s a song or piece of music that always makes you feel emotional or romantic?

Why We Love Funny People: The Psychology of Humour
Humour is a big deal when it comes to attraction – it’s like social glue, bringing people closer together. Psychologists say our attraction to people who make us laugh comes down to both evolution and social factors.
From an evolutionary point of view, a good sense of humour signals intelligence, creativity, and problem-solving skills, all traits we tend to look for in a partner. Plus, laughter triggers endorphins, those natural “feel-good” chemicals that help us feel more connected and build trust.
Humour is also a great way to handle stress and tough times together, which can make relationships stronger.
At the end of the day, sharing a laugh creates happy memories and builds emotional closeness. Who doesn’t love that?
The Science Bit of Date Night Humour
If you’re interested in the science behind why sharing some giggles with your date is as effective as a night of oysters, maca root, chillies, strawberries, and honey, we’ve tried to explain it as simply as possible.
The outward expression of laughter relies on two neural pathways that are semi-independent.
- The first pathway is the involuntary system, which involves the amygdala.
- The second pathway is the voluntary system, which involves the prefrontal cortex.
It turns out our brains have a laughter-coordinating centre, which means that multiple parts of the brain work together to decide what we find funny. No wonder humour can be so tricky to pin down!
Danish-American comedian Victor Borge said it best: “Laughter is the closest distance between two people.” And honestly, most of us would agree – laughter has a way of bringing us closer together.
Whether you’re joking around with your partner or cracking up at a comedy show, there’s no denying the power of laughter. It’s that shared moment of laughter that connects us. That’s exactly why throwing in a funny question or two on a first date can work wonders.
Put Your Funny First Date Questions to Use With Finding The One
With the Finding The One dating app, we prioritise genuine connections by encouraging you to meet in person rather than getting lost in endless online chats. This means you can put your first date jokes and sense of humour to the test face-to-face, creating authentic and meaningful relationships.
Download the app today, take the first step towards discovering your perfect match, and let your shared humour truly shine.
FAQs
Why Are Fun Questions Effective on a First Date?
Asking funny, lighthearted questions on a first date is the perfect way to cut through the tension and anxiety. Laughing is a natural stress reliever, and making each other laugh is the perfect way to create a deep, natural bond.
When’s the Best Time to Ask a Funny Question on a Date?
Timing is key when it comes to successful dates, from being on time to knowing when to make a move. This also applies to asking funny questions. It might be tempting to jump straight in to break the ice if you’re nervous, but this can be off putting.
Coming in with the jokes straight off the bat can make your date feel like you’re not taking it seriously. It’s best to make some casual small talk and settle into the date before busting out the funny questions.
Should You Ask Deep Questions on a First Date?
Yes, but keep it balanced. Deep questions can build a meaningful connection, but avoid overwhelming your date early on. Start with lighter topics and gradually ease into deeper conversations as comfort and rapport naturally develop during the date.
What Flirty Questions Can I Ask on a First Date?
Flirty questions or pick-up lines can be playful and light-hearted, such as “Did it hurt when you fell from heaven?” or “How come you’re so perfect?” Keep it fun and genuine to create a relaxed and enjoyable connection.
What’s a Good Spicy Question?
A good spicy question could be, “What’s one thing you’ve always wanted to try but haven’t yet?” It’s playfully intriguing and opens up the conversation for exciting and personal exchanges without being overly intense or forward.
