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Funny First Date Questions: 16 to Make Your Date Laugh

Funny First Date Questions

Are you arranging an initial meeting with someone you like, and need amusing and maybe even flirty, ice breakers? 

Making a good impression from the outset will up your chances of finding someone you can spend more time getting to know. Humour is a fantastic tool for bonding. So arriving armed with some funny first date questions is a great way to make your date laugh. 

In this article, we’ll give you ideas for questions and help you to build a fun rapport with the other person. 

Funny first date questions

Your sense of humour is part of your personality. While not everyone finds the same things funny, exploring what does and doesn’t make you laugh, can be a great way to identify if you’re compatible in the longer term. It’s also a lot of fun. And let’s not forget, if you can make your date laugh or smile, they’ll be much more inclined to like you. Nothing will move you from an awkward and shy place to a relaxed one faster, than a good giggle. 

Questions to make your date laugh

It’s tough to come up with questions that’ll be funny in themselves. So the key is often to prime your date with an amusing question, that solicits a hilarious response. Once you become better acquainted it’ll get easier to do this. As you’ll know which stories and experiences are likely to draw this out. Meantime, you can try some of these questions to make your date laugh. 

Funny first date questions to ask men

According to Time, humour can make us irresistible. Research published in the magazine suggests that women prefer men who make them laugh. And men are more attracted to women who laugh at their jokes. 

Here is the first of our funny first date questions…

#1 What are the unwritten rules of your workplace? 

Tease out all the silly things that go on during the 9 to 5. This will help you to understand more about their career, without a dull conversation about work. 

#2 What’s the best prank you’ve ever pulled?

If they can’t think of one, ask if they’ve ever had a good one pulled on them, or witnessed one. Then have your own funny prank story ready. 

#3 What’s the most ridiculous thing you’ve ever worn?

There’s likely to be a story attached to this, so it’ll get the chat going. 

#4 Would you rather live in a vending machine, or be a vending machine? 

Hypothetical ‘would you rather’ scenarios are very silly, but beneficial in breaking the ice and taking the pressure off deeper topics. 

Questions to make your date laugh

#5 Which animal is the biggest party animal?

This steers the conversation into more hypothetical and lighthearted areas. It’s nonsense but can really lighten a heavier mood.

#6 What skills do you have that would help you survive a zombie apocalypse?

Another silly, hypothetical one, but this actually gives you some concrete info about their skills (whether assumed or real).

Flirty first date questions

If you can learn how to flirt naturally and effortlessly, you’ll be able to convey a sense of attraction, without having to explicitly call it out on your first meet. Your date will be looking out for signs of interest, particularly if they’re not the presumptuous type. So if you think it’s going well and you’re feeling a spark, drop in some flirty questions to clarify your stance. 

#7 Are you ticklish?

Anything that suggests close physical contact is mildly suggestive. Say this with a cheeky smile and possibly an eyebrow raise, to up the ante. Do not, however, go ahead and tickle somebody you don’t yet know. 

Funny first date questions to ask women

Don’t forget, these questions are interchangeable across the genders too. Work out which ones you’re most comfortable with. And create your own unique versions. 

#8 What’s the worst name you could give your child or pet? 

Find out what it is and why. This will likely become a shared debate and provide an opportunity for humour. You’ll also likely find out if they have any existing pets and children. 

#9 If peanut butter had a different name, what might it be?

Any answer to this is likely to incite some giggles… Mushed nuts? Beige paste? Pulverised peanut? And it’s a great way to check they don’t take themselves too seriously.

#10 What should never ever be listed as BOGOF? 

This stands for buy one get one free and is an amusing acronym itself. Plus it’ll get them thinking, but not too hard. There are plenty of funny things you wouldn’t want to get two for the price of one. 

#11 If you had to be an object for a month, what would you be? 

A bizarre question, but you may discover what their values are and which possessions they value most. And the fact that you’re even asking them this strange question, will be likely to make them smile. 

Questions to make your date laugh

#12 What food would you eat if you had to eat one food non-stop until you were sick?

Another silly one to make them smile. It’ll also be informative in terms of their culinary preferences (so you know which restaurant to suggest or meal to make for the next time). 

#13 If you would ever be caught for a crime, what would it be?

Hopefully, this will be hypothetical too! You’ll get to find out about their naughty side though and perhaps reveal any cheekiness in their character. 

Short funny questions

It may be that you’re short on time. Speed dating questions, for example, have to be kept very brief, as you have a finite period in which to familiarise yourselves with one another. 

#14 What’s your guilty pleasure?

Open-ended, this can apply to TV shows, celebrity crushes, food and drink and anything else that may pop up in the chat. It feels like you’re delving into more private areas of their life while keeping the chat light-hearted. It’s also sure to lead into a further conversation around the thing or person they choose. 

#15 Pool or hot tub? Discuss.

A quirky opener, say this with a wry smile and an eyebrow lift to evoke a smirk from your date. 

#16 Which was the best Ninja Turtle?

Take the same approach as the question above, for this quickfire preference question. Or come up with your own… Who’s your favourite ever Coronation Street character? Which fruit rocks? What song should never have been recorded? 

Don’t forget to consider all your own answers too. Your date may arrive primed with his or her own questions and if you’re someone who finds it hard to think on their feet, you’ll do better if you’ve prepped. 

Embarrassing date questions

Just to be clear, what you’re aiming for should be light-hearted, witty or silly. Steer clear of anything that even closely resembles offence. That may work with your friends after a few drinks, but it won’t fly in this situation. Keep it gentle and kind in the early stages. You may soon discover you both have an acerbic sense of humour or shared cutting sarcasm. Fantastic. But until you’ve spent some time getting to know each other, tread with care. Similarly, don’t embarrass them. Stay away from very personal jokes that could be seen as being at their expense. And don’t be lewd, unless it becomes patently obvious you’re both on the same page. 

Having some questions up your sleeve is very useful. But having sharper humour all around will help you be funnier off the cuff. And this can be invaluable in a date situation, where everyone is likely to feel nervous. (You can read more about how to combat first-date nerves). You can enhance your own comic chat, by absorbing some funny podcasts and TV shows. This will help you to understand the nuts and bolts of how to be funny and win over many potential new suitors. 

Related Questions

Should you kiss on the first date?

The stats for first dates that end in a kiss are around the 50% mark. It depends on how you’re feeling and the vibes you’re getting from the other person. If in doubt, look into their eyes for a bit when saying goodbye. A pause and some silence can provide the opportunity to lean in for a kiss. 

How do you end a first date?

Even if you don’t want to take it any further, always end politely and kindly – without giving false hope. If you do want to see them again, you might like to suggest another meeting to see how they react. Do this tentatively if you’re unsure. Or you could message them afterwards if it feels easier.

How do you rock a first date?

Make an effort. Dress to impress (appropriately to the venue and time of day). Have some talking points and questions ready, but be sure to allow space for them to lead the conversation too. Listen to them, make regular eye contact, smile and stay engaged. Have good manners and be polite, but have fun!

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