50 Funny First Date Questions

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They say that laugher is the way to a woman’s heart. So here’s 50 funny first date questions to keep conversation flowing on your first date. Not only should these bring a smile, but also enable you to get to know her a little better – with nothing too heavy to begin with.

50 Funny First Date Questions

With so many funny questions you could think of, how do you pick which ones are best for a first date? 

Well, in this post, we’ve gone for a mix of funny icebreaker questions and funny would you rather questions. They’re light, easy, but not so random they verge of weird!

Have a read, see which ones stand out, which ones stay in your mind, which ones flow from there. Then SAVE this article to remind you of some funny liners, as and when you need.

The more familiar you are with the different things you can ask / say on a date, the easier it will be. Plus of course, it’s all about practice! So have fun and be confident. Here’s some suggestions to get you started…

Funny Ice Breaker Questions

So let’s kick off our funny first date questions with some key ice-breakers. They’re related to you, your date, or just dating / relationships in general.

  • So… what’s one item of clothing I could have worn today that would have made you want to turn around and walk away from this date?
  • What’s the most embarrassing thing that you, or someone you’ve been with, has worn out in public? Just so I know for next time hey… don’t want to make the same mistakes!
  • What’s been your worst ever haircut? You tell me yours, I’ll tell you mine.
  • Have you ever had any nicknames? Any embarrassing ones? Spill the beans!
  • What’s the sexiest and least sexiest name you can think of? Male and female?
  • What’s been your worst date… to date? Come on, fill me in.
  • Who would be your DREAM celebrity date? Don’t hold back, don’t worry, I won’t take offence! 
  • What random habits do you find insanely annoying? Either your own, or others. Any pet peeves?
  • What’s one food you couldn’t live without, and one food you think would be the BIGGEST PUNISHMENT if you had to eat it every day? Uh huh, didn’t expect that second part, huh?
  • What’s a weird food combination that you actually love?

Funny First Date Questions

Let’s keep the funny first date questions coming. Embed them in your brain, embed them in your brain!

  • If you had to pick a cartoon character that best resembles – first, you – and second, I – who would you choose for each?
  • If you could be a DJ, what would your DJ name be? Or, pick one for me, I’ll pick one for you!
  • If you had to walk 1,000 miles, which celebrity would be your worst / best to walk with? 1,000 miles remember. This person will either keep you going or drive you crazy!
  • What’s your favourite karaoke song, and if you were to pick a duet for us, which song would you pick?
  • What’s the worst chat-up line you’ve ever been told? And yes, I’ll only be a tiny bit devastated if you actually say one of mine!
  • Okay, let’s turn this around. If you were to see me at a bar for the first time, right now, and was feeling brave, what chat up line would you say to me? (Give her an encouraging wink with this one!)
  • If you could switch genders for a day, what’s the first, second, third (and so on) thing you’d do?
  • If you could read people’s minds, what do you think you’d be most surprised to hear?
  • Are you any good at accents? If so, let’s hear the one you’ve mastered the most!
  • Have you ever pulled off an absolute gem of a prank? If so, when, how, what? Tell me all.
Funny First Date Questions

Random Questions

Before we get onto some funny would you rather questions, let’s break it up with some funny “what is” questions. There’s some slightly random ones in here, but it will get the two of you thinking!

  • What’s the weirdest smell you’ve ever smelt? (Dig deep!)
  • What’s the most ridiculous fact you know?
  • What’s the worst song that ever hit the chats? Suggest some options if needed.
  • Whats’ the funniest joke you know?
  • What’s the most imaginative / hilarious insult you’ve ever come up with?
    Not got one? Have a think now! See what you can both come up with on the spot!
  • If you were arrested with no explanation, what would your family and friends assume you had done?
  • What’s one wrong thing you believed to be true / didn’t know, which you recently found out?
  • What animal would you most like to have as a pet if it was totally safe and friendly?
  • If you could be a fly on the wall, who would you most want to listen in on?
  • What’s the funniest thing that’s happened to you in the last week?

Funny Would You Rather Questions

Next up, let’s look at some funny would you rather questions, perfect for a first date. Now the chances are, you won’t remember all of these off by heart. But that’s okay.

Have a read, get inspiration (also re-read right before a date to keep them in the forefront of your mind) then throw them out there once the two of you are comfortable and have reached the “mindless chatter” stage of the date.

So, let’s go…

Would You Rather:

  • Be unable to move your body every time it rains or not be able to stop moving while the sun is out?
  • Have to walk around barefoot, or walk everywhere in 6 inch heels?
  • Be invisible at a party or constantly have to be the life of the party?
  • Talk like Yoda or breathe like Dark Vader for the rest of your life?
  • Be without elbows or without knees? / Without nails or without eyebrows? etc.
  • Eat only cheese for 1 year or not be able to eat cheese for 1 year? (Change the food to see how it changes the answer!)
  • Have the names of all of your past dates tattooed over you, or skin that changes colour based on your mood?
  • Randomly time travel every time you cough or teleport to a different place on earth every time you sneeze?
  • Be able to read the minds of everyone you get eye contact with, or jump into another person’s body every time you focus on them and say “body swap, body swap, body swap”, ten times?
  • Be physically fit and healthy, or financially free and loaded?
Funny First Date Questions

Would You Rather Questions For Dates

Let’s round up our funny first date questions with some more “would you rather” ones. These focus specifically on dating and relationships (which are often more relevant for a first date than some of the random ones.)

They’re also pretty insightful – telling you more about the person and what they’re like, whilst still keeping things light and fun. Win, win. So we’ve got…

Would You Rather:

  • Smile at a guys bad joke every time, and make him feel good about himself. Or put him out of his misery and tell him the truth… they’re just terrible! (Is honesty always the best policy? You’ll soon find out!)
  • Forget your date’s name one hour into a dinner date, or accidentally call them by your Grandad’s name (and let’s say that’s one that’s totally cringey… Like Nigel or Bernard! Something totally off the mark.)
  • Run into your most recent ex on a first date, or run into both of your parents?
  • Only be able to speak by singing or a first date, or every time your date asks you a question, you have to get up and do a three-second wiggle dance before answering?
  • Snort really loudly every time you laugh on a first date, or share an intimate first kiss after eating a bowl of onions and garlic?

Would You Rather:

  • Go on a date with someone who can’t eat or drink anything before they’ve posted it on Instagram (and won’t let you do the same either!) Or go on a date with someone who live tweets the entire date? On the plus side – there could be some comedic value in the latter one.
  • Have a boyfriend who told every person he walked past that he loves you, or have a boyfriend who only told you he loves you, once in a blue moon?
  • Realise 10 minutes into a first date that you’ve been out with this person before (and it didn’t end well the last time!) Or accidentally call them by your ex’s name three times in a row? (And they know it’s your ex’s name.)
  • Go two years staying single, without going on a single date. Or stay single for two years, but go on a different date every day?
  • Go a month without any physical contact (no hugging, no kissing, no nothing.) Or go a month without being able to speak to anyone (no calls, but texts allowed)?

That’s All For This One

So there we have it! 50 funny first date questions to get you thinking, and hopefully, her giggling.

These are just a starting base, with some suggestions. Pick the ones you like the best, and the ones which would most naturally flow from you, then add them in on your date.

Hope this helps. For more tips and tricks, browse our latest articles here.

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