50 Interesting Questions to Ask When Online Dating

Finally, you’ve got the chance to make your first debut with your potential partner.

Tired of sexy pickup lines?

Do you want to get them smiling on the other side of the screen?

Research conducted on 237 adults showed that the very first interaction after seeing a dating profile or reading the first message brought about predictions on the fate of that relationship. 

Talking to a stranger online could be exciting and magical, but these feelings fade in a few seconds if the first messages aren’t well-thought. Asking questions that reveal your intentions and most importantly your personality is important.

This article lists 50 suggestions for you to pick. 

50 Online Dating Questions to Ask

1. What's The Most Amazing Adventure You’ve Ever Been On?

If you have noticed in his/her profile that they are adventurous this is a good icebreaker to initiate conversations. It also implies that you want to experience an adventure together in the future. 

2. What Are You Most Passionate About?

Asking for their passions never fails. It is a good way to indicate that you’re interested in knowing their interests without risking appearing dirty as many do in dating apps.  

3. What Is A Typical Day Like For You?

This is a thoughtful way of learning more about their life, daily routine, and how they spend their free time. It also explains why they reply late (e.g they might be working from 8 PM to 5 PM).

4. What Are The Top 3 Most Important Things On Your List?

Priorities. What they put on top of their list indirectly reveals their personality characteristics (e.g putting family, friends, and work shows they’re compassionate and reliable). 

5. What Is Your Favorite Type Of Music/Favorite Song?

Music brings people together and this question might lead to a day-long conversation if you share similar preferences.

6. Who Is The Most Important Person In Your Life?

Is it their mom, dad, or someone else? Not only will this question reveal important insights about their personality but also gives you clues on how to continue conversations without making them feel bad.

7. How Important is Alone Time for You? 

This question helps you find out if they can cope with loneliness well, or they always need someone nearby. It also gives a clue about their maturity and how independent they are. 

8. What’s Your Star Sign? 

Not everyone likes the horoscope but in most cases, it nudges the conversation into moving towards other topics you want to talk about. (e.g “Oh, you’re a Leo! You must be really courageous!”

9. Who Inspires You? 

Knowing who inspires them gives you clues into what traits they appreciate the most in a person. 

(Note: If it’s an actor, keep it in mind for when you suggest her/him movies later. 😉

10. What Would Your Ideal Weekend Look Like?

There are a million reasons to ask this question starting from understanding how they’d prefer spending free time to know if you’d be able to meet them on a weekend. 

11. Have You Read Any Good Books Lately?

This question not only shows that you are a reader and well-educated person, but also that you’re interested in knowing their literary tastes. 

(Note: if you’re both bookworms, suggest them book clubs to join together.

12. Are You a Planner or a Spontaneous Person?

It will help you understand how organized they are. If you’re the kind of person who prefers punctuality a spontaneous partner might irritate you. 

13. Have You Ever Had a Life-changing Experience?

Asking this question will reveal an unknown part of their life. 

Maybe they don't have an answer at first for this unless they have an amazing story to tell but asking it will lead to interesting conversations. 

14. If You Could Live Anywhere, Where Would It Be?

It will help you to understand what standards they want to have for their future. Would they be enough with having a good life in a well-off part of the country or do they want a lavish lifestyle somewhere abroad? 

15. If You Could Have a Superpower, What Would It Be?

A slightly childish question but guaranteed to make your conversation more enjoyable. It also gives you insights into how grounded they are (e.g they might consider this childish stuff).

Pro Tip: Always communicate carefully and do not give away your personal details to stay safe on dating apps.

16. What Always Makes You Laugh?

If there’s something you would want to remember about them, is this. Knowing what makes them laugh will come in handy when you want to surprise them or make them go through difficult moments.

17. What Is Something You’ve Always Wanted To Try But Have Been Too Scared To?

This question will bring out a little of their adventurous spirit and you will understand their fears. 

18. What Did You Love Most About The Place You Grew Up?

This an interesting question that will make them realize that you care about their background which has shaped them into the people they are today. 

19. If You Had To Name One Thing That Really Makes Your Day, What Would It Be?

This question will add more “ammunition” to the “arsenal of love” when you try to fight their sad moments. If you want this to work out then you should definitely want to know how to make their day. 

20. What Do You Hate Most About The Dating Process?

Not everyone sees dating with the same perspective as you do. Knowing what they don’t like about it will help you approach that part of the process smoothly. 

21. What Is One Thing In Your Life That You Wish You Were Doing but You Aren’t?

Everybody has regrets. Knowing theirs guides you towards what should you help them with to alleviate the pain of these regrets. 

22. What Are You Better At Than 90 Percent Of The Population?

A little weird and funny question at the same time but that will make them think about their uniqueness. What they think makes them special is what you’d want to help them develop further. 

23. What Are the Characteristics Your Ideal Partner Should Have?

Through this question you keep notes of what your partner wants, so you can see if you have certain characteristics or not. And if not, you can start working on what you see is feasible to achieve. 

24. Are You A Dog Or Cat Person?

Knowing what animal they prefer will lead to conversations about pets where you’ll find more similarities that strengthen your bond.  

25. Are You More Of A Morning Person Or a Night Person?

This question gives you an important clue about the best time to message them. Also, it gives you important insights into whether your routines would match if you were a couple one day. 

26. What's The Best Advice You Have Ever Received?

It will show you what they tend to value the most in life and also what they have been struggling with. Usually, the best advice is the one that guides us out of hardships. 

27. Tell Me Your Favorite Childhood Memory?

Childhood is where we have the greatest joys and sorrows. Learning what she/he remembers the most will help you understand her behavior and moral values too. 

28. What's The Most Important Lesson You Have Learned So Far?

Peek into their self-growth path, wisdom, and struggles. The question in itself sounds a bit formal so make sure you ask it at the right moment when you’re talking about a similar topic. 

29. How Would You Describe Yourself?

How they explain themselves shows a lot about their personality. Are they selfish or humble? Also, how they see themselves shows about the things they want others to compliment them about. So keep it in mind. 

30. Do You Have Any Unusual Hobbies?

That’s the part when it gets exciting. Find out what unusual things roam their mind and discover their wild side. Talking about or doing these activities together will bond you closer. 

31. How Do You Prefer To Be Remembered By People?

This question will help you discover what they value in themselves, and what they want to be distinguished for. That’s where their insecurities might lay as well so encourage and compliment them here. 

32. Do You Enjoy What You Do?

Profession plays an important role in the broader perspective of life. This question will help you find out whether they are passionate about what they do. It also reveals whether they are optimistic or pessimistic. 

33. Tell Me About Your Family.

Showing that you care to know about their family means that you’re truly interested in knowing them. Shows that you’re not looking for a quick hook-up without feelings, and this sets you apart from others. 

34. Do You Enjoy Traveling?/What’s Your Favorite Place?

Do they have an adventurous spirit or they’d rather sit home and binge-watch Netflix? This question helps you find out. 

35. What Did You Like About Me?

Knowing what they appreciate in you makes it easier to keep them always impressed. Moreover, it gives clues on what others value in you and what you should work on developing further in yourself. 

36. What's Your Dream Job?

Do you want to find out how many things you have in common and what they love doing? Discover their dream job. 

37. Who Do You Talk With The Most?

Is there a friend or relative they usually share everything with? Finding out who this person is, lets you know how to behave appropriately when talking about them. 

38. What Goals You’d Like To Accomplish In Your Life?

We’re still digging into their passion and inner desires. You better keep notes as showing support on their path to reaching their goals will bring you closer. 

39. What Are You Most Afraid Of?

Everyone has hidden fears. Maybe they fear darkness, snakes, closed spaces, or heights. It’s good to know before sending them a TikTok video with snakes. 

40. Are You An Introvert Or Extrovert Person?

Discover what type of person they are. If they ask you for suggestions one day you’d want to suggest places that match their personality so they don’t feel left out. 

41. What Kind Of Child Were You? 

Their childhood years have shaped their character. Learn more about those days. Also, you might stir up warm memories that lead to beautiful nostalgic conversations. 

42. What Do You Care The Most About?

What do they value the most in life? Asking this question helps you figure out what they prioritize the most and against what priorities are you “competing”. 

43. What Advice Would You Give to Your Younger Self?

Growing up we reflect on our mistakes. This question helps you discover their regrets, and what they have struggled with the most. 

44. What’s Your Favorite Saying Or Quote? 

Everyone has a quote that has stuck in their mind because it deeply resonates with their beliefs. Knowing it helps you discover traits they can’t explain about themselves in their own words. 

45. What Do You Care Least About? 

Knowing what doesn’t matter much about them is equally important as knowing what does. It helps you understand their self-esteem (e.g saying that they care less about themselves might mean they lack self-love) or things you wouldn’t want to focus on. 

46. If You Could Change Something In The World, What Would It Be?

Know their ideals and the vision of a perfect world. This also shows what they would want to try to find in the world or work towards achieving. 

47. What’s One Thing I Should Know About You?

Maybe they have something important that could bond or separate you. The sooner you find out what it is, the better. You’re aiming to create a closer connection with each other here. 

48. What’s Your Idea Of The Perfect Life?

Similar to the 46th question, this will help you find out their idea of perfection. Eventually, this helps you understand what they seek from a partner.  

49. What’s An Accomplishment You Are Really Proud Of?

These eight words will help you find out in what stage of life they are. Is it a job promotion, university diploma, or personal project? 

50. What Do You Do When You're Deeply Mad Or Sad?

It’s best to know it beforehand so their reaction after an argument doesn’t shock you. 

Similar Scoops
21 Questions For A New Relationship
50 Amazing First Date Questions To Spark A Conversation
50 Flirty Questions To Ask On Your First Date

About Mary J. Gibson

Mary J. Gibson, director of DatingXP.co, is a renowned love and relationship coach whose expertise is widely acknowledged across the industry. Her insightful guidance and profound understanding of romantic relationships have earned her features in prestigious publications including Bustle, AskMen, Cosmopolitan, and Elite Daily. Committed to staying ahead of trends, she continually broadens her knowledge by conducting incisive interviews and forging dynamic relationships with emerging dating services, ensuring her advice remains relevant and impactful.