72 First Date Questions, Conversation Starters & Things You Must Never Ask

First dates are full of nerves and dreaded awkward silences. Best way to fill them? By preparing some interesting questions to ask on a first date. You’ll be chatting in no time!

First dates are always uneasy affairs. Unless you’re extremely confident or really smooth, the first few minutes can play a big part in helping you get a sense of whether your first date will have a happy ending or not. The best way to get the easy conversation flowing is by a pre-date preparation of some interesting first date questions and conversation starters to break the ice.

In reality, first dates are a bit like a job interview, but the conversation doesn’t have to feel like an interrogation.

If the conversations just start to feel like a series of questions to your date, they may look forward to ending the meet-up instead of asking for another one! [Read: Dating rules all classy guys and girls should know]

First date questions – What you need to know

Surface-level questions are easy to ask, but the perfect questions are ones that go beyond small talk and lead to conversations that help you get to know whether the two of you will vibe well or not.

We recommend avoiding getting personal or saying anything that may leave your date feeling awkward or embarrassed. Relationship experts advise to check their body language, too, as that will help you determine if they are comfortable sharing personal details about themself.

You may be nervous, but that’s no reason to say the first thing that comes into your mind. We’ve got a long list of great first date questions to ask that you can use and impress, but remember to mix your questions, so it’s a good blend of short and long answers.

Also, remember that some of the people you meet may be shy or may need a few minutes to open up and talk to you. Say something about yourself to help them feel more comfortable or smile warmly. It’ll surely help your date feel more relaxed.

To help you use our ‘perfect for a first date’ questions in the right way, keep these pointers in mind. [Read: 26 things to talk about on a first date to make them like you instantly]

1. Don’t interrogate your date

The first thing you need to know about first date questions is to avoid throwing one question after another at your date.

Wait for your date to respond with their answer, or look at the menu for a few seconds to see if your date’s ready to ask you a few questions, or maybe use the moment to segue into asking their favorite dish.

You don’t want a first date to feel like you’re about to shine a light in their eyes and drag their answers out of them!

If they don’t answer or try to avoid the question, that’s fine, let it go. There are better ways to get to know your date, and this one is not one of them. [Read: 15 things to do on a first date to make your date fall for you]

2. Mix up your questions

The first date questions below are a good mix. Start with the simple and fun questions to ask as a way to see how much of a talker your date really is.

That will help you decide what open-ended questions to use to have many more conversations that’ll make you seem like a great conversationalist.

3. Don’t just stick to the list

Use a few of these first date questions to help you get things warmed up and then, forget all about these questions. The more you try to stick to a list of questions, the lesser your chances of impressing your date.

You’ll be so focused on jumping from one question to the next that you won’t get a chance to see if you can turn a question into an exciting conversation. [Read: 15 obvious flirting signs to know if someone enjoys talking to you]

4. Don’t memorize the list

That’s the worst thing you can do. If you sit in front of your date and recite one question after another, they might feel like they are in a job interview. We’ve already established that’s a no-no.

Read these first date questions, keep a few in your mind or store them on your cell phone, and use them as icebreakers when the conversation starts to run dry.

The best first date questions for great conversation starters

Before you even try asking these perfect first date questions, read this very effective guide on what to talk about on a first date.

You can definitely use those tips to create great icebreakers and natural conversations that’ll make you a charming smooth talker instantly. And once you mastered the art of conversation during a date, slip these date questions in, and work your magic!

1. Do you like this place?

2. What do you usually like to drink? [Read: The most popular alcoholic drinks and how to prepare them to impress anyone]

3. How’s your appetizer/main course?

4. Have you come here before? / Do you come here often?

5. How was your day? [Read: 13 romantic dinner date ideas for two]

6. Where do you work? / What do you do at work?

7. What kind of music do you listen to?

8. Do you listen to podcasts?

9. What’s your favorite cuisine?

10. What is your go-to restaurant?

11. What kind of movies do you like watching? [Read: Easy movie date tips to have a great date]

12. What do you do after work every day?

13. What do you do for fun / What are your hobbies?

14. Do you have any pet peeves?

15. Where did you study?

16. What’s your favorite vacation destination to unwind?

17. What’s your idea of a good time / conversation? [Read: How to talk to anyone – Master the art of a real conversationalist]

18. Are you a cat or a dog person?

19. If you ruled the world, what would you change?

20. Which parent are you closer to?

21. What are your biggest turn-offs or red flags in someone you’re looking to date? [Read: 35 biggest dating turn offs for girls]

22. Would you rather… dress in casuals or formals?

23. What do you think about chick flicks, and which was the last one you saw?

24. Do you always look this good? / Are you always this charming?

25. Do you like to read, or are you more into watching the screen?

26. Who’s the person in your own life you admire most?

27. Are you the type of person who likes spontaneity, or do you like predictability and routine?

28. Who do you speak to when you’re having a hard time in love? [Read: 13 signs your friends are ruining your relationship]

29. Do you have a childhood memory that makes you smile every time you think of it?

30. If you could travel the world, which are the five places you’d never miss?

31. So what’s your current passion or pursuit in life?

32. Are you close to your family?

33. What do you hate most about meeting someone on a first date?

34. Are you a night owl or early bird person?

35. Which part of your body is the most ticklish?

36. How old were you when you had your first crush?

37. What happens on a regular guys’/girls’ night out with your friends? [Read: When is the right time for a guy to call after a first date?]

38. How would you define a relationship?

39. So how long ago was your last relationship? [Read: Things to keep in mind to make your first date just perfect]

40. What did you think of our date today before we met each other?

41. And what do you think now? [Read: How to end a date – The good, bad and ugly way]

42. Where are you from originally?

43. What subject do you wish you had studied?

44. What does your typical day look like?

45. What do you like to do outside of work?

46. What movie did you see last?

47. Have you read any good books lately? / What is your favorite book?

48. What was the last series you binge-watched on Netflix? [Read: Netflix and chill – How to do it the right way]

49. Did you have a family pet when you were younger?

50. What would be your death row meal?

51. If you won the lottery, what would you do with the money?

52. What is the scariest thing that’s ever happened to you?

53. What is the most embarrassing thing you’ve ever experienced?

54. Which superhero did you like as a kid?

55. What superpower would you choose to have?

56. Who is your celebrity crush? [Read: 18 signs your date clearly likes you on your first date]

57. What is something you want to learn or wish you knew as a kid?

58. If you could travel back in time but couldn’t interact with anything, when would you go back to?

59. Would you rather have a night in or a night out?

60. Where are we going on our second date?

61. Would you like to have a nightcap elsewhere? [Read: Why there’s nothing wrong with having sex on the first date]

62. What are you up to for the rest of the weekend?

What not to ask your date, ever!

Curiosity isn’t a crime, especially when you’re getting to know someone. However, there are times when you should let your curiosity slide, just to ensure you don’t end up blurting out something completely uncalled for.

Here are some of the first date conversation topics that you may be tempted to ask on the first date, but you never should, especially as you’ve just met them.

1. How much money do you make?

If you’re on a date, you can usually assume that the person you’re with can at least pay for their half of the expenses. For now, that should be enough.

You can talk about work but not how much they earn annually, how much they paid for their car or how much their mortgage is. This isn’t one of the questions people ask on the first date- save it for later on down the road when things get a little more serious. [Read: The biggest dating turn offs for guys]

2. How many people have you slept with?

Not only is it rude, but it will also put your date on the spot. In all honesty, it will make them feel like you’re prying too much into their life, and your date is going to turn awkward, if not completely sour.

Unless you’re already in a committed relationship *and even then, it shouldn’t really matter*, the number of people your date has bumped uglies with should not concern you in the slightest. [Read: 24 worst things guys can say on a first date]

3. Do you want to have a threesome? *or indulge in some sexual fantasy*

Unless you met your date at some huge swingers party, or on Tinder and went buck-wild, then there is no reason to ask your date if they’d be open to having a threesome. When it comes to questions on a first date, this is a huge no-no!

Asking questions like this just makes you look like you’re looking for a wild night between the sheets… with a potential third person involved.

4. Is your friend single?

Usually, when someone asks you out on a date, it means they are interested in you. They take the time to plan a great date night, and not to be a matchmaker.

It will all go out the window the minute you start to show that you are attracted to someone else, particularly your date’s best friend.

It doesn’t matter if it was innocently asked; It will just get your date wondering if you only went out on the date for the purpose of getting closer to someone else. [Read: The warning signs of a bad first date and red flags in the first few dates]

5. Why do you look better in your photos?

Thanks to technology, we can filter our photos as much as we want. The downfall to editing photos all the time is that when we meet people in person, we may not always look like our profile pictures.

Unless you’re complimenting your date on their superb Instagram filtering or Photoshop manipulation skills, your date may be able to find this question a lot like a thinly-veiled insult.

6. Do you have any STDs?

This is one of the first-date questions, without a doubt, you should avoid! For sure, it’s important to know if you might end up sleeping with someone who has an STD. But come on, don’t ask it outright!

If you’re at the stage where sleeping with each other is still far off into the future, leave the STD talk for a time when you’re considering getting busy in the bedroom. [Read: How to have safe sex in every single way it is possible to]

7. Have you ever cheated on someone

Okay, so this one is a bit tricky. Some people are quick to divulge this information, particularly if either of you mentions details about your past relationships. However, asking your date outright if they’ve ever been unfaithful might catch them off-guard.

It will make them think you’re already assuming that they’re the cheating type. That kind of mistrust so early in your blossoming romance will only make your potential relationship wither and die. [Read: To cheat or not to cheat – A guide to make up your mind]

8. What did you do wrong to make your last relationship end?

Don’t ever assume that your date is the one who messed up their last relationship; it’s very presumptuous. Instead of asking this question, phrase it more tactfully like, “You’re such a great person, I wonder why your last relationship didn’t work out so well.”

Or even better, just don’t ask so early in a budding relationship.

9. When was the last time you had sex?

Just like asking if your date has STDs or how many people they’ve had sex with, this question only makes you look like you’re way more interested in sex than anything else.

If you don’t want to look desperate, don’t ask this as one of your first date questions. [Read: How often should you have sex?]

10. Do you think you could love me?

Now, THIS is desperate with a capital D! If someone loves you, you shouldn’t feel the need to ask them outright. Even if you think your date might be too shy to say the words, forcing them to answer this potentially uncomfortable question may only end in one of two ways.

One, your date may love you, but you’ve robbed them of actually coming up with their own terms to confess their love.

And two, your date might not love you, and this can only end with them thinking that you’re just so presumptuous that you had to ask this question.

Even if love hasn’t even been considered yet, just mentioning it is going to dampen the atmosphere completely. [Read: The biggest reasons why saying the L-word too soon sucks]

The most important thing to do on a first date? Relax!

Now you have plenty of first date questions to use sparingly throughout your conversation. It’s good to know that you have these questions in your back pocket in case the conversation starts to stall. That should give you confidence.

However, the most important thing you should do is just to chill out and relax. By doing that, you’ll be able to just be yourself and allow your wonderful personality to shine through. When you do that, your date will be so charmed, they’ll want to arrange a second date.

[Read: How to ask for a second date and not fumble or appear too eager]

These first date questions are really easy to use at any point in your date. Try them, and you’ll definitely seem like a fun conversationalist and leave a great first impression too!