51+ Funny First Date Questions

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What are fun questions to ask on a first date? Funny first date questions to keep conversation light and entertaining? Well, we’re about to fill you with inspiration as we run through our top 51+ funny questions to ask on a first date.

What makes funny questions so great on a first date? Well, because they help to ease your first date nerves and lighten the mood. Dating can – undeniably – be a little bit scary. 

But if you go into it, full of funny first date questions that you can use to really “break the ice”, the two of you will start to relax in no time at all, making the date easier, more enjoyable and actually, more of a success! 

So what are we waiting for? Let’s jump straight in…

51+ Funny First Date Questions

Here’s some of our favourite funny first date questions. Have a read, re-save this list before your next date, and see how many you can remember before you go in!

Don’t worry… you don’t have to get them spot on.

It’s not about having them word-for-word, but simply getting you thinking of the kind of things you could ask to direct the conversation in an interesting way, whilst still covering the essential things to talk about on a first date.

See we think we’ve struck the balance of funny first date questions that are:

  1. Not too weird: you don’t want to scare your date off!
  2. Not totally random: these don’t help with forming a connection at all.
  3. Actually quite interesting and entertaining (just what we want!)

How To Lead Into The Questions

A quick tip before we get started now then…

When it comes to how to lead into these funny first date questions, you might like to first start with some of these questions to ask someone you just met.

This builds a base foundation for the two of you to begin with!

After that, try not to fire these funny first date question off, one after the other, or ask them at complete random either.

Instead, tie them into the current conversation that you’re having, or say something before (that’s relevant) then casually lead into the funny question.

So for example, let’s pick the question:

“Do you talk to your pets? What do you say to them?”

If you came out with this at complete random, it would be WEIRD! However, if you asked them first if they have any pets, then continued on with something like…

“Ah cute. I bet you talk to him all the time, don’t you? A friendly hello every time you see him, right? Your little mate! What else do you say? Ask for a cuddle after a bad day? Come on… spill the beans!”

You see? You can make it funny and teasing. (Flirting by teasing is a great flirting technique by the way so it’s a great, simple way to incorporate this in!.)

It will also then come across as far more natural, as opposed to pre-rehearsed / trying too hard… Not to mention, make the conversation flow far easier too. (Amazing!)

So now we’ve got that covered, let’s get stuck in. Here’s some of our favourite funny first date questions to get you thinking…

Funny First Date Questions

Funny First Date Questions

So, in no particular order, here’s 51+ funny first date questions to throw in on your next first date. See you could ask…

1) Have you ever had somebody call you the wrong name and not had the heart to correct them? If so, what did they call you?

2) What inappropriate moments have you found yourself getting the giggles, when you really shouldn’t have? (Be honest – I won’t judge!)

3) What’s the most embarrassing thing you’re afraid of? Or something you’re scared of that most people don’t find scary?

4) What’s the longest lie-in you’ve ever had?

(Based on this, you might end up ruling out your next morning date ideas, and sticking to afternoon. Ha!)

5) How bad is your road-rage on a scale of 1-10?

6) Have you ever been on the receiving end of a practical joke? Or successfully pulled one off?

7) What’s the worst nickname someone has ever called you?

8) What did you normally get told off for when you were younger? In fact, paint a picture of mini-you and what you were like. Let’s see if I can picture it!

9) Do you have any claims to fame?

10) How about any secret hidden talents?

Funny Questions To Ask On a Date

11) What “old person” things do you do?

12) Is there anything you believed as a kid, for way too long?

13) What fad did you never really understand?

14) What things do you love doing, that people would never guess about you? Or the weirdest thing about you that most people wouldn’t imagine?

15) Do you have any guilty pleasures?

16) What’s your favourite guilty-pleasure show on TV?

17) If someone only saw your Spotify or Netflix accounts, what kind of person would they think you are?

18) What’s your go-to song for singing in the shower? 

19) What’s always guaranteed to make you laugh?

20) Do you laugh at stale jokes politely, or find it hard to pretend?!

Funny Questions To Ask On a Date

Funny First Date Questions About Dating

21) What’s the most embarrassing thing to happen to you on a first date?

(There’s actually heaps of interesting questions to ask about dating if you want a conversation that’s entertaining!)

22) What was your very first kiss like?! And how old was you when it happened?

23) If you were to give your younger self, one piece of dating advice, what would you say?

24) How nervous do you get on dates? (Be honest!)

25) If you could dress me in anything, for the rest of this date, what would you put me in? Actually… let’s break this down into 1) if you were being nice and 2) if you were trying to embarrass me! 

26) What would you rate me as a date so far? (You can be brutal if you need!)

27) What was your very first impression of me, in one word? Don’t hold back!

(Quick-fire this question too, to get your date answering before they’re able to fully think. It’s far funnier that way, as both you or they, don’t know what they’re going to come out with!)

28) What wrong first-impression do you think most people get about you?

29) What’s on your mind right now, at this very moment? (Come on, no filter!)

30) Are you a drunk texter? Where all your feelings and emotions come out?

Funny First Date Questions

31) If you could drink one alcoholic drink and not get drunk, what would it be?

32) What smell of alcohol reminds you of a bad night on liquor? 

33) What’s the worst movie you’ve ever seen?

34) How quickly do you eat the popcorn at the movie theatre? 

35) Are there any weird food combinations that you love, but most people would find strange?

36) What food could you simply not live without?

37) What’s some of the cringiest thing you’ve ever googled?

38) Are you a clumsy person? What’s the silliest accident you’ve ever had?

39) When you are procrastinating, what do you usually do to avoid the thing you’re meant to be doing?

40) If you had to give me a PowerPoint presentation right now on one subject, what would you be able to do with ease?

how to keep conversation entertaining

Funny Questions To Ask On a Date

41) Which cartoon character would you say you most resemble?

42) How many selfies do you take in order to get the perfect selfie? (Or is it a challenge?!)

43) Have you ever been told you look like anyone famous?

44) Who’s your most embarrassing crush? Or past crush? (Be honest!)

45) Which famous person do you find attractive, that most people wouldn’t?

46) If you could pick a celebrity for a new best friend, who would you choose?

47) If you were a DJ for the night, what would your DJ name be?

48) Are there any accents that you can mimic? If so, I want to hear!

(Be brave – share yours too! And don’t forget to add those regional expressions in for the full effect!)

49) What’s something you’ve tried, but would never do or have again?

50) If you were to do one thing to try to impress me right now, what would you do?!

51) What’s the WEIRDEST thing that you think, actually, makes you a bit of a catch?!

That’s All For This One

So there we have it – 51+ funny first date questions (that are actually totally original!)

Can you see how you can start to tie them into conversations? And that – actually – you don’t need to tell lame jokes to still get a lot of laughs out?! 

In fact, by asking funny, original questions, you’re guaranteed to get far more giggles… genuine ones too! Uh huh, you can thank me later.

So have fun. Be confident! And go out and enjoy yourself.

Dating, really is, all what you make it. (Like most things in life!)

Take care!


Funny First Date Questions
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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