51 Key Online Dating Questions to Ask Him 

Looking for love on Tinder, Bumble, or one of the many online dating sites?    

You and every other eligible person out there are slogging through the morass of candidates, trying to find that one needle in the haystack.

You may feel overwhelmed and directionless with so many options (and men) available. 

But one thing’s for sure: when it comes to finding a partner online, you need a strategy. 

Asking him the right dating questions can help you sort the “maybes” from the “no ways” and have a head start on finding your Mr. Right.

What Should You Ask Someone You Just Met Online? 

Once you have matched, it can be challenging to know your next steps.

You may feel you don’t have enough information about the person to further the conversation or worry about seeming too intrusive. 

Luckily, the right conversation starters for your date can get the ball rolling; you only need to know which questions to ask and when.

  • Find a balance between questions that allow you to get to know the person on a deeper level and questions that keep things light and fun.
  • Try to get some of your non-negotiable questions out without sounding pushy (for example, don’t ask whether they want kids right away).
  • Craft questions that help you learn about a guy’s values, goals, and interests.
  • Don’t get too personal. Wait to ask questions about ex-girlfriends, salary, religion, politics, or sex.

The main point is to keep it light while gently probing for more information that will enlighten you on whether he is good first-date material.

If he is, you’ll have plenty of time to learn more about him.

51 Essential Online Dating Questions to Ask Him 

We have divided the questions into various categories to make it easier for you to find the most relevant ones.

Good Online Dating Questions

1. What’s the most daring thing you’ve ever done?

This is a great question to discover your date’s exciting adventures. It can be a fun way to talk about the risks they’ve taken and the things they’ve accomplished. And you can see if your risk tolerance matches his.

2. What hobbies do you enjoy?

While this question may sound cliche, it is an important one to ask. Knowing what kinds of activities one enjoys can give you a better idea of their interests and passions.

3. If you could travel anywhere in the world, where would it be and why? 

This is a great question to explore their dreams and aspirations. It can provide insight into the places they’ve always wanted to go to and what cultures and experiences they find fascinating. 

4. What are your favorite movies, TV shows, and books? 

One of the ways to get to know someone is by finding out what they like to watch and read. It can open up a discussion about which genres of media they are most interested in, and it can also help you to know if you two share similar tastes in entertainment.

5. What would you do if you had an extra day off each week? 

Asking this question can be a fun way to get them thinking about what activities they would like to pursue if given the opportunity. If they say, “Going out and getting hammered with the guys,” that’s good information for you.

6. What one thing could you not live without?

For some, it may be an electronic device, while for others, it may be a particular item of clothing. Regardless, finding out what that one thing is can open a conversation about why it is so important to them.

hands holding a phone with a profile of a man online dating questions to ask him

7. What would be the title if someone wrote a biography about your life?

This is one of those deep and thought-provoking questions. It is a great way to get someone thinking about the importance of their life experiences and what kind of legacy they would like to leave behind.

8. What’s something that you’re really proud of accomplishing?

This question is great for finding out what one values and what aspects of themselves they are most proud of. It can be something small, like learning a new skill, or something bigger, like overcoming a personal challenge. 

9. What’s your biggest pet peeve?

The answer to this question can give you an idea of the kind of things they may not tolerate or accept in a relationship. 

10. What’s your funniest memory with your friends? 

Some of the best memories come from time spent with friends, making this a great question to ask. Not only is it fun to hear about their most humorous moments, but it can also give you a glimpse into their relationship with their friends. 

11. What is your idea of a perfect date?

The perfect date can be very subjective, so it’s great to get their opinion on what they consider the ideal romantic outing. Knowing might help you plan one for the two of you if things work out. 

12. Do you have any hidden talents?

It’s always fun to find out something new about somebody, and a hidden talent can be just the thing. You’ll learn something new about them, from playing an instrument to a special skill. 

13. Which song has the most meaning for you?

Music can be a powerful form of expression, and asking which song has the most meaning for them is a great way to get to know their innermost thoughts and feelings. It can also open up a conversation about why the song holds such meaning for them. 

Questions to Ask a Guy on a Dating App

14. If you could have one superpower, what would it be?

Chances are, they’ll have an interesting answer to this question that will tell you a lot about their personality and interests.

15. What caught your eye about my profile?

It’s always nice to know what made someone interested in getting to know you, and it may even prompt a conversation about the qualities you both find attractive in others. 

16. Are you more of an introvert or extrovert?

This question can give you an idea of how outgoing your date is and how comfortable they are in social situations. If one of you is an extreme introvert and the other is a true extrovert, that might spell conflict down the road.

17. What is the best surprise you’ve ever had?

Nothing can put a smile on someone’s face like the memory of a great surprise. Asking them to share this experience can make for a fun conversation, and it may even give you ideas for a future surprise. 

18. Is there something that’s always been on your bucket list?

Bucket list items can be very diverse, and it can be interesting to find out what kind of experiences and adventures your date wants to have in their lifetime. Whether it’s swimming with sharks or bungee jumping, this can lead to a fun discussion about what they want to do. 

19. What are your thoughts on commitment?

Asking this can help you get a better understanding of their views on relationships and help you make sure that your expectations are aligned. 

20. How do you de-stress after a long day?

Everybody has their own way of unwinding and relaxing after a long day. From reading to yoga and meditation, it can give you an idea of what kind of activities the guy likes to do in their free time.

woman forming heart hands while guy is on video online dating questions to ask him

21. What’s the best quote that you’ve ever heard?

This question can be a fun conversation starter, as there are many great quotes. You never know what kind of unique words of wisdom he might share. 

22. What was the last thing you learned that impacted you?

Learning is a lifelong process, and finding out what kind of new information has made an impression on him recently can be interesting. Whether it’s a book he read or something he learned from someone else, this can be a great way to get him talking. 

23. What’s one thing you would never do again?

We all have experiences we would rather forget, and this question is a good way to find out what kind of things he doesn’t ever want to repeat.

24. What topics could you talk about for hours?

For this question, you must be open-minded and ready to explore different topics, such as politics, history, psychology, or even video games. And remember to ask for a fun fact about their favorite topic.

25. What would you do if you won the lottery tomorrow?

This is a classic question that can tell you a lot about someone’s priorities in life. Do they want to travel the world, open their own business, or just enjoy a worry-free life?  

26. Are there any values that are especially important to you?

Knowing what values someone holds dear can give you a better understanding of their character and behavior.

27. Do you believe in fate or that things happen for a reason?

This is a great philosophical question that can lead to a lively debate. It’s a good way to find out if he has any spiritual beliefs and how he views the concept of fate and destiny. 

28. What would you do if you could turn back time?

Life can be full of regrets, and this is a great way to talk about those moments. It can be interesting to hear what one would change in their life if they could and the different paths they may have taken.

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29. What is the most outrageous thing that has ever made you shriek in public?

While whatever happened was probably embarrassing for him, this is a fun and humorous way to get an interesting story out of him. 

30. What is the most embarrassing nickname someone has ever called you? 

Nicknames can be embarrassing, funny, and even cringe-worthy. It can be amusing to hear what kind of nicknames someone has had in the past and how they got them.

31. Would you rather unknowingly snore in a silent library or fart loudly on a crowded bus?

This is a classic “would you rather” question that can be a fun way to lighten the mood. It’s an amusing way to get your date laughing, and it can also reveal their sense of humor. 

32. What is the silliest thing you’ve ever cried about?

It’s okay to let your emotions out. This question can help you both bond over the fact that sometimes you just can’t help but cry over silly things.

33. Have you ever tripped and fallen in public?

You will be surprised how such a simple question can lead to some hilarious stories.

34. What’s the weirdest dream you’ve ever had?

Dreams can be strange and have symbolic meanings, so this is a fun way to get your date talking about the subconscious mind. 

35. What is the funniest pick-up line you’ve ever heard?

Pick-up lines can be cringy, but they can make for funny conversations. It’s not just the creativity of the line but also the context and sometimes even the delivery that can make it funny. 

36. Name something you laughed at but probably shouldn’t have? 

This question can get your date to reveal their silly side. We all have those moments when we laugh at something inappropriate—for example, when someone clumsily trips and falls in public. This is a fun way to reminisce about those moments.

37. Have you ever made a bad pun or joke, and it backfired?

We all experience bad puns and jokes, but they can still make for some hilarious conversations.

Feel free to weigh in on whether or not you think the joke was actually bad or if it was just a case of bad timing and delivery. It could spark an interesting debate. 

38. What’s the funniest reason you heard someone give for why they were late? 

Have you ever heard an excuse so ridiculous that you couldn’t believe what you were hearing? Well, your date might also have heard a few of them, and this is an excellent way to get them talking about it.

39. What is the most ridiculous dare you’ve ever accepted? 

Dares can be fun but can lead to some of the craziest stories. It could even reveal the side of your date that loves to take risks and push the boundaries. 

woman holding phone slightly smiling online dating questions to ask him

40. What’s the strangest encounter you’ve ever had with an animal?

From pets to wild animals, this is a great way to get someone to share some of their funniest animal stories. It’s also a great ice-breaker if your date is an animal lover. 

Fun Tinder Questions

41. If you could be any celebrity, who would it be? 

It can be interesting to hear who your date would choose as their celebrity alter-ego. It can also reveal what they aspire to be and the type of people they look up to. 

42. What’s the most interesting random fun fact you know? 

Random facts can be an entertaining way to start a conversation. And there is always something to learn, no matter how mundane or weird the fact may be.

43. What’s the most outrageous outfit you’ve ever worn? 

We all have those moments when we look back and cringe at what we wore. 

44. What’s the most embarrassing thing your parents have ever done to you? 

Parents can be embarrassing sometimes, and this question can get your date to share their funniest moments with their parents. It could also lead to some interesting conversations about generational differences and how each perceives certain situations.

45. Who is the funniest character from a movie or TV show?

Funny characters from movies or TV shows can make us laugh and bring up some interesting conversations. Who knows, you might even have the same favorite character. 

46. What’s your go-to karaoke song?

Karaoke songs can bring out the inner singer in us, and this question is a fun way to find out what your date loves to belt out.

47. Are you a cat or a dog person? 

The classic debate. It’s not just about which animal you prefer but also why you choose it over the other. 

48. What’s the silliest thing you believed as a kid?

We all have those moments when we look back and laugh at how gullible or naive we were. 

49. What are your thoughts on the pineapple pizza debate?

You’ll be surprised how heated this pizza debate can get. Find out if your date is a pineapple on pizza supporter or an opponent and why they feel that way. 

50. What’s the most clumsy moment you’ve ever had? 

Nobody is perfect, and almost all of us have those moments when something goes wrong – for example, spilling your drink on someone or tripping over your own feet. These situations can make for a funny story to share.

51. What’s the most unusual date you’ve ever been on? 

Sometimes the most interesting conversations come from the weirdest experiences. Find out what your date did on their most memorable, unique date.

Final thoughts

Conversation topics for online dating don’t have to be boring or intimidating. All you need is to ask the right questions and be open to their answers and unique perspectives. This will help you connect and get to know your date better.

Online dating has become a trend, especially among young adults these days. Here are some online dating questions to ask him to keep the chats going.

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