60 Fun and Interesting First Date Questions

Let’s face it. First dates can be terrifying. Picture this: You’ve done the hard part and managed to ask your crush out on a date and they said yes. Now they are seated next to you at your favorite café all glammed up, and your brain goes to sleep. Suddenly, you have nothing to talk about and anything you say sounds awkward.

Your palms are sweating, knees are weak, and the date seems to be sailing straight into an iceberg. Thankfully, it doesn’t have to be that way because we will help you out. Below is a comprehensive set of first date questions that will let you know your date better, get the conversation going, and increase your chances of getting a second date.

Best ‘First Date’ Questions

1: What’s your favorite hobby?

Hobbies make us happy, and they are linked to our personalities. It’s a great way to get to know your date better.

2: What is the last book you read?

Everybody loves a good read, and literature is definitely something that you can bond over.

3: What TV series can’t you stop re-watching?

We all have that one series that we can re-watch anytime.

4: What is the last thing you googled?

It’s a funny and interesting question to get the conversation started.

5: Who is your favorite music artist?

Shawn Mendes, Lil Wayne. You want to get to know someone, head straight to their playlist.

6: What is the top item on your bucket list?

It’s a great way to know what to plan for the second date.

7: What is the name of your pet?

Instead of asking whether your date has a pet, ask for the name of the pet. They will likely tell you more if you frame the question this way.

8: What is your most bizarre talent?

Funny and interesting way to get the conversation started.

9: What is your cheesiest pick up line?

There are a fair number of cheesy pick-up lines out there, and your date probably has the cheesiest one you’ve ever heard.

10: What is your favorite app on the phone?

You probably shouldn’t be on your phones during the date, but a question about an app will get things going.

11: What is your greatest accomplishment so far?

People love to talk about their accomplishments.

12: What do you hate about dating?

It’s a sly way to know what to avoid when dating that person.

13: What is your spirit animal?

You will get some interesting and funny answers with this question.

14: Where is the most beautiful place you’ve been?

You can try and top her most beautiful place on the next date.

15: Do you like your boss?

We spend most of our days at work and a lot of conversational material lies there.

16: How would you describe your ideal holiday?

Ideal holidays look great in our minds, and you can try to make your date’s dream come true.

17: What was your favorite TV show as a kid?

The TV shows we watched as kids stick with us forever, and they hold some of our happiest memories.

18: Are you an indoors or an outdoors person?

It’s a great way to know how to plan that second date.

19: What is craziest thing you’ve done?

Crazy stories make for funny conversational material.

20: Are you a morning or night person?

We all have our preferences and the reasons we love our preferences.

21: Which family member are you closest to?

Family is a great place to start a conversation.

22: What is your favorite childhood memory?

Our childhoods have the best memories, and again, they were our happiest times.

23: Which is the last movie you watched?

Maybe there’s a new release out, and your date hasn’t watched it. Great second date idea.

24: Which is the longest period that you’ve remained single?

One month. A few years. The answers you get might surprise you.

25: Describe the worst date you’ve been on.

Do not repeat the mistakes of that worst date if you want to stay in that relationship.

26: Coffee or alcohol?

You are either seated next to a party animal or a café person or both.

27: What is your favorite meal?

Everybody loves food, and you might find that you have similar taste buds.

28: What is your guilty pleasure?

These nasty pleasures make for good conversational fodder.

29: What’s your opinion on online dating?

If you met online and you want to know how the date is coming along, ask this question.

30: When did you have your first kiss?

Very few people had a perfect first kiss, but maybe your date did.

31: What would you change if you went back in time?

Past mistakes stick with us, and there are some we wish that we could reverse.

32: What is your dream job?

Get ready for some interesting answers with this question.

33: Which job would you never do?

Once you get the answer to no. 32 above, follow it up with this one.

34: Who is your celebrity crush?

Justin Beiber. Zoe Kravitz. Wayne Rooney. You can’t predict the answer to this one.

35: What is your most surprising fact?

You might find out that your date shared a desk with your celebrity crush.

36: Which is your favorite sports team?

Sports unite us, but the answer to that question might divide you and your date. It’s better you find out early or risk being on separate sides during the local derby.

37: What would you tell your 20 year old self?

Ready yourself for some fun and heartfelt answers to this question.

38: What do you look for in a relationship?

If you really like your date and want a relationship, pop this question.

39: What household chore do you hate the most?

Doing the dishes. Taking out the trash. Laundry. It could be anything or everything.

40: What is the ideal city to live in?

I hear Nairobi is quite the city. What does your date think?

41: What assumptions do people make about you?

Some assumptions are quite funny.

42: What would you do if you won the lottery?

Travel to the Bahamas. Donate to charity. The answers to this question are interesting.

43: How did you meet your BFF?

This question will draw a smile cause we all love our BFFs.

44: What is your perfect karaoke song?

It would lead to a fun date if you are at a karaoke bar.

45: Can I get you another drink?

It looks like a basic question, but you might get an witty answer.

46: Do you prefer calling or texting?

The answer to this question will aid future conversations.

47: What is the most weird fact you know?

It’s a great way to know if your date is a Nat Geo fan.

48: What is your most embarrassing fact?

Your date might have to be a little bit tipsy for them to reveal this one.

49: Who is your favorite actor?

You might disagree on this one, but you’ll have an awesome conversation.

50: What is your favorite smell?

You might get a great idea for your next cologne.

51: How did you spend your last holiday?

Is there a holiday coming up? You’re date might have some ideas.

52: Cars or motorcycles?

This is a great question for a petrol head. A 70s charger makes for a great birthday gift.

53: What is your favorite quote?

Winston Churchill had some great quotes, and so did Barack Obama. Maybe your date has some original quotes of their own.

54: Do we split the bill or you’ve got it?

The age old question. Get ready for some funny answers.

55: What would be your ideal second date?

The date’s gone well. You’ve had fun. Why not ask about that second date?

56: What are your kind of people?

This would be a good question if you are thinking of introducing your friends.

57: Do you like surprises?

Some people don’t like surprises. It’s good to know at the first date.

58: What is your silliest fear?

Fears are real, but some are quite silly.

59: Do you rehearse what to say before you pick a call?

Does your date pick the phone up at the first ring or is there is a rehearsal first? I’d want to know.

60: What is the worst advice you’ve heard?

Hopefully your date didn’t heed to it.