25 fantastic second date questions you should know about

Don't want to embarrass yourself on your second date? This list of questions will make things flow smoothly.

Dating Expert David Hall September 27, 2022 • 10 minutes read
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Second dates are often not much easier than the first date. You want to make a good impression, but you also don’t want to seem like you’re prying into your date’s personal life.

And just imagine you can’t think of anything to talk about. Awkward silence can be really daunting and ruin the whole experience in the worst case.

Don’t worry, though; we’ve got you covered with a list of questions that will help keep the conversation going without being too intrusive. Most of these questions are also very funny, actually! So, here are our top questions to ask on a second date:

Safe second date questions

Safe questions are just that. You can ask them without worrying about getting too personal or crossing any lines. The downside is, though, that too many of these questions can become boring very fast.

A good rule of thumb is to ask follow-up questions whenever your date answers one of these questions. For example, if they mention that they love animals, you can ask about their pets or what kind of animals they’re most interested in and why.

1. What’s your favorite TV show?

This question can quickly turn into a passionate discussion about shows and movies. It also gives you a good idea about your date’s taste in entertainment.

2. Who is your favorite band or musician?

Everybody loves music! So, this question is amazing and can lead to talking about concerts and music festivals that the two of you might want to attend in the future.

3. What’s your favorite book?

This is a great question for finding out what your date is into. If they don’t have a favorite book, you can ask them what kind of books they’re into and why. If they don’t read, you might want to move on.

4. What’s your favorite food?

This is a safe question that can lead to talking about other favorite foods. It’s also a great way to find out if your date has any dietary restrictions that you should know about. It can also turn into a discussion about different cultures and vacations if your date is up for it.

5. What were you like as a kid?

This is a great way to find out more about your date’s childhood. You can ask about their favorite memories, the most daring thing they ever did, or what kind of trouble they used to get into.

Personal second date questions

These questions are a bit more personal and can help you get to know your date better. They’re still safe to ask but be prepared to answer them yourself as well.

6. What are you looking for in a relationship?

This question can help you determine if your date is looking for something casual or more serious. It’s also a good question to ask if you’re looking for a relationship as well. It’s better to ask this question earlier rather than later on in the relationship.

7. What’s your family like?

This question can help you figure out how close your date is with their family. You can ask about their parents, siblings, and grandparents. If they’re close to their family, they’ll probably be close to you as well.

8. What are your hobbies?

This question can help you figure out what your date is interested in. Do they like to be active, or do they prefer to stay at home? Are they into art or music? This question can also lead to talking about other interests and things that the two of you have in common.

9. What’s your favorite place to go on vacation?

This question can help you figure out what kind of vacations your date likes to take. Do they prefer to stay in one place, or do they like to travel around? Are they into adventure, or do they prefer to relax? This question can also lead to talking about other places that they’ve been to.

10. What’s your favorite memory?

Probably everybody has a favorite memory, if they know it or not. You can ask them about why the memory is so special to them and if they have any other memories from that time period. This question can also lead to talking about dreams and aspirations if your date is up for it.

Fun second date questions

Everybody loves fun! These questions are meant to be light-hearted and can help you get to know your date’s sense of humor. They’re also great conversation starters and can create many funny moments!

11. What would you do with a kiosk in your room where you could order anything you want for delivery to your room without even having to speak?

This question is great for finding out your date’s favorite food. It can also be a fun way to talk about all of the different things that you would order if you had such a kiosk.

12. Do you think you could go without speaking for an entire day?

This question can help you figure out how talkative your date is. Some people might be able to go without speaking for a day, while others might not be able to last more than an hour. It can also lead to talking about why the person thinks they could or couldn’t do it.

13. If you could have any superpower, what would it be?

Superheroes are in! This question can help you figure out what kind of person your date is. Do they want to be able to fly? Be invisible? Read people’s thoughts? The possibilities are endless.

14. If you could trade places with anyone in the world, who would it be?

A question like this can help you figure out if your date wants to be famous or not and if they are happy in life. It can also lead to talking about why that person would want to trade places with someone else. Maybe they would want to be in a different profession or have a different lifestyle.

15. What’s the funniest thing that’s ever happened to you?

This question is a great way to get your date to loosen up and start talking. They can share a funny story from their childhood, college days, or even just something that happened recently. It’ll be sure to make you both laugh.

Deep second date questions

Deep questions are fantastic for getting to know somebody on a deeper level. But you don’t want to overdo it with the deep stuff at your second date, though. It can turn a fun conversation into a heavy and awkward one real quick. So, ask deep questions sparingly and only if you feel like your date is comfortable enough to talk about this stuff.

16. What’s your favorite thing about yourself?

A light-hearted yet deep question. This can help you figure out what your date likes about themselves and if they are comfortable talking about it. It can also lead to them sharing things that they don’t like about themselves, which can give you more insight into their personality.

17. Do you have any regrets in life?

This is a deep question that can lead to a lot of soul-searching. Your date might not want to answer it on the second date, but if they do, it can be interesting to hear what their regrets are and why. It can also give you an idea about how your date handles difficult emotions.

18. What’s your biggest fear?

This question can be hit or miss. Some people might not feel comfortable answering such a question on the second date. But it can also lead to talking about other fears that the two of you might share and be a light-hearted conversation. It really depends on the person you’re asking.

19. What are you passionate about?

This is a great question to see if your date shares any of your interests. It can also lead to talking about why the person is passionate about what they’re passionate about and how it’s affected their life.

20. What’s the most interesting thing about you?

It can be hard to think of something interesting to say about yourself. But this question can help your date do just that. They can share something that they’ve done, a hobby they have, or even their job. It’ll give you a little more insight into who they are as a person.

Awkward second date questions

There are lots of awkward questions you should avoid asking. If you feel like the situation and your date can handle one of these, go ahead and ask one of them. Just be very careful, as these questions can quickly turn a fun conversation into a date full of awkward moments.

You’re not really experienced in dating? Then you should know about these second-date tips!

21. How many people have you been in love with?

This question can be a little too personal for some people. It can also lead to talking about past relationships, which can be awkward on a second date. If you do ask this question, be prepared for your date to not want to answer it.

22. What’s your biggest turn-off?

This question can be a bit of a downer. It’s probably better to avoid it on the second date unless you’re trying to see if your date is compatible with you. In which case, it might be worth asking.

23. Are you where you want to be in life?

This question can lead to a lot of heavy conversations. It’s probably best to avoid it on the second date unless you’re both comfortable talking about this stuff. Otherwise, it might just make things awkward.

Many people actually don’t like the path they’ve taken in life, and this question can really open up that can of worms. But some people will react positively to such a question, so it really depends.

24. How much do you weigh?

This is a very personal question that you should only ask if you’re already pretty close to the person. On the second date, it’s probably best to avoid this question unless the person brings it up first. Especially women can be very sensitive about a question like this, so better avoid it.

25. What’s your least favorite thing about yourself?

This question can be difficult to answer. And it’s probably not a good question to ask on the second date, as it can lead to a lot of negative conversation. It might be better to wait until you know the person a bit better before asking them something like this.

There you have it – 25 questions you could ask on a second date. Some of them are deep, some of them are light-hearted. But all of them can help you get to know your date a little better. So go ahead and try out a few of these questions the next time you go out with someone new!

You’ve still got the second date ahead of you and don’t know what to write them? Find out what to text after the first date!

You don’t just want to ask questions but also want to have a great conversation? Then find out what to talk about on a second date!

How to win at early stages dating: The ultimate list of books

If you're looking for books about the early stages of dating, you've come to the right place. We've put together a list of some of our favorite books about dating, all of which are perfect for early stages in a relationship.

  1. Dating Sucks, but You Don't: The Modern Guy's Guide to Total Confidence, Romantic Connection, and Finding the Perfect Partner
  2. Seven Secrets of Modern Dating: The He Said, She Said Guide for Getting from Single to Spouse
  3. First Date Mastery: The Complete First Date Psychology Guide For Men
  4. Just Send the Text: An Expert's Guide to Letting Go of the Stress and Anxiety of Modern Dating
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Dating Expert

David Hall

David Hall is a self-taught dating expert who works as a freelance writer to help people improve their love lives. He has always been interested in dating, physical attraction, and …

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