Online dating questions are always a hot topic to many people, especially women. Initiating a conversation and keeping it going are among the essential aspects of online dating.

To be successful in this process, you must first be comfortable talking to the person in a fun and non-threatening manner.

This will allow you to know more about them. This article will discuss 50 best questions that you can ask when online dating to get the conversation started.

So, keep reading to find out more.

50 Online Dating Questions to Get the Conversation Started

You can take all the time in the world perfecting your online dating profile, but it will be of no use if you don’t know the ways of breaking the ice and getting the conversation started.

So, here are 50 questions:

1. What's interesting about you that people don't know about?

This is quite an ice-breaker because it is a bit flirtatious and mischievous. It is an indication that you want to know him deeper than the surface level.

2. What is it that you're most passionate about?

This type of question gives you an insight into what he strongly feels `- is he heartfelt and spirited? It is a great way of determining whether his level of passion matches yours.

3. What is your dream job?

For ladies, this is a good question to ask your man on an online date because a person’s dream job portrays their passion, meaning, as well as their lifestyle. Is it the money, the enjoyment, or the impact of the job?

job at office

4. What type of things do you find extremely funny?

Once your conversation has taken off and has become serious or awkward, use this question to divert to a carefree topic. Every person likes to talk about what makes them laugh.

5. What is the most memorable time of your life?

This is a great question to ask if you’d like your conversation to be meaningful and reflective. It will allow you to learn more about his life story.

6. What did you do when you were a kid that you miss the most today as an adult?

This can get him to become quite reminiscent and it is playful. Maybe it was camping or vacation. It will help you know if you share something in common.

7. Who is the person that you talk to often?

When you ask your man this question, his response will inform you more about his closest people in life. You can know whether he has a close bond with his siblings or parents.

8. What was your day like?

This may seem like a basic question, but it gives you a glimpse of how his day was, his responsibilities, how he manages stress, his tone, and how he spends his time.

9. Do you cook? Which dish is your favorite to cook?

This is a great way of knowing whether he has culinary skills and the kinds of food that he likes. Food is always a great conversation topic.

10. Do you consider yourself extroverted or introverted?

Is he a party animal or is he a shy guy? This question will enable you to know his personality.

11. What is your favorite holiday destination?

Is he a person who likes luxury? Is he adventurous or just prefers cozy indoors? The response to this question will reveal these answers.

12. Which kind of food do you like the most?

Asking your online date this question will help you determine if you share the same foods. As mentioned above, food is always a safe conversation topic.

food dating

13. What do you do for fun?

This is a question to test your compatibility. He may not be a nature lover whereas you’re an adventure enthusiast.

14. Which is the longest relationship that you've ever been in?

If you’re looking for just a hookup and he only prefers long-term relationships, you may be out of luck.

15. If you had the option to live anywhere in the world, where would you live and why?

Asking this question can help you to easily know what his interests are about that place. You could even make plans together if you share the same interests.

16. What annoys you the most about people?

This is an interesting and safe topic to talk about. Does he hate flaky people or people with no integrity? This will help you in making sure you don’t display those traits.

17. Do you have any hobbies? If yes, which ones?

Before you go out with someone, you need to first establish if you have any common hobbies such as traveling or sports. From this, you will know whether they like relaxing when they’re away from work.

18. What do you consider to be your best quality?

It is always a great idea to learn what your man’s best qualities are. It will help you know how much he values himself.

19. Do you believe in love?

Well, some people believe in love while others don’t. Has he been hurt several times before?

20. Which is your preferred sport?

When having a conversation with a person you’re intending to have a romantic relationship with, it is important to understand the person’s strengths and interests such as sports. Men certainly love talking about sports.

21. Which sport would you not want to play?

Asking this question helps you to know what to talk about appropriately. Here, you can also ask him why he doesn’t like playing a certain sport.

22. If you would have a superpower, which one would it be and why?

His choice will determine what it is that he would like to change about himself presently. He may say that his superpower would be supersonic speed so that he could be there with you.

23. Would you like to go out sometime?

Asking a man whether he would be interested in going out with you some time helps you to determine whether he is genuinely interested in you.

24. What type of things often make you laugh?

Just thinking about funny things is enough to put someone in a better mood and livens up your conversation. It is a fun question because you will know whether they have a sense of humor.

25. What is your greatest goal in your life at the moment?

People love talking about themselves. Ask him what he intends to achieve in life and you will get to know his goals and ambitions.

26. What type of music are you interested in?

The main reason why people ask this question is to determine whether you share the same taste of music which in turn could indicate whether you’re compatible.

27. Have you been in love with two women at the same time?

This inquisitive question shows you whether he is a person who can commit or he is just looking for a fling.

28. Have you broken someone's heart before?

You’ll be in a position to find out if he’s a bad boy when you ask him this question. Here, you can also ask him the reason why he broke her heart.

29. What's your opinion on tattoos? Do you have one?

Asking this question is a sly manner of asking him about his body without overtly being sexual. Make sure that he is comfortable talking about it. If not, change the topic instead.

30. Is there something that you're obsessed with?

Whatever or whoever he is obsessed with, you can poke fun at his obsession kind-heartedly.

31. Do you still have something you had in your childhood?

There is something innately funny about childhood habits. Moreover, it will help to open up a great conversation.

32. What do you do when you get bored?

It is always a great idea to ask about a person’s interests when having a conversation. It makes the conversation livelier.

33. Would you give up technology for one week?

Here, you can spice it up by challenging him to abstain from technology and see who folds first.

34. What is the lamest joke that you have ever had?

This question will have him smiling and laughing. After all, no joke is lame if it is delivered properly.

35. What is the best picture on your phone? Do you mind sending it to me?

He will not send you photos if you fail to ask. Therefore, you can ask him to send you his favorite picture.

36. What keeps you up during the night?

When you share your worries with a person, it makes them open up more with you intimately.

37. What are you up to this weekend?

Small talk is always effective. This question will help you plan if you can meet him physically.

38. What did you do during your last vacation?

Just like interests, it is essential to know how your date likes to spend their time, especially during vacations.

39. If working was no longer an obligation and you had a lot of money, what would you do the entire day?

This type of question can help to bring a playful, light, and untethered feeling into your conversation. It will also help you determine whether he is an active person or more of an indoors person.

40. When you look at a lady, what's the first thing that you notice?

Men notice different aspects in a woman. Therefore, knowing what a particular guy is looking for will help you identify whether he will find you attractive.

41. What is the funniest thing that you've ever experienced in high school?

This conversation starter gives the other person an opportunity to think about their funny stories and express them to you.

42. What scares you the most in life?

Just like asking a person which sport they dislike, this question allows him to have a more intimate conversation with you by sharing his weakness.

43. When growing up, did you have any nicknames?

This question is bound to make him laugh. It may be a bit embarrassing but it allows a great, light-hearted conversation.

44. Which hidden talents do you have?

See the talents that he possesses. If he is intending to learn a new thing, it shows that he is inquisitive.

45. Which are the best restaurants around your town?

When you ask a person this question, it helps you to prepare yourself mentally for where he might take you should you decide to hang out.

46. Did you see that viral TikTok, Instagram, or Twitter video?

Since everyone has access to social media, it is common for people to have seen a particular viral video. It can help to lengthen the conversation and make it livelier.

47. Do you have a role model? If so, who is it?

When you know the role model of a person, you can learn about their motivation and direction in life.

48. I'm quite nervous about (insert something personal). Have you done it before?

When you talk about the personal information of a person, it could increase how likable they are to you.

49. What is the important thing that I need to know about you?

When you ask a person this question, you’re trying to assess if the person would be a great fit for you.

dating advice by krys

50. How do you celebrate festive season holidays?

Since we are approaching the festive season, it is essential to determine how the person you’re talking to spends that time. It can help you decide whether you will spend that time with them.

Putting it Together

You will be in a position to get an online dating conversation started with these questions and avoid awkward silences. Conversations help you to learn more about the other person’s values, hopes, and dreams, world views, goals, and expectations.

Most importantly, these questions will help you determine whether you and the person you’re talking to are compatible. Is it worth going on a physical date with that person? Technology has made it easier and more convenient to find love.

So, why not give it a try?

Krystyna Trushyna
Krystyna is a blogger, coach and iDate speaker. She has been working in online romance and International dating industry since 2012 and is passionate about identifying the romance scam and giving dating tips and hacks. Join Krystyna for the dating service reviews and for finding ways to succeed with dating.
Krystyna focuses on International dating, which involves teaching men communication skills in a cross-cultural environment. She has been featured in many major publications including DatingAdvice, Space Coast Daily & SWAGGER Magazine.
Looking for more information? Feel free to get in touch to ask your questions or give feedback (see here: Contact Krystyna).