Questions to help you understand a guy better

Just because the conversation doesn't go well on the first, fifth (or fifteenth) date doesn't mean the romantic potential is over. Sometimes, we just need a little " lubrication " to get things moving and get to know our special new friend better.

" Who would you like to tell your life story to? " can be a clever conversation starter, along with " What did you want to be when you grew up? " However, if you're like us, those deep questions don't automatically come to mind when you're trying to woo a potential love interest.

This set of questions is for the average non-social ninja who wants to get to know a guy better. Some of the questions are personal—like asking him if he believes in soulmates or what his biggest relationship issues are—while others are pretty silly, like whether he likes it cool or hot all the time, or whether mustard or ketchup is his favorite condiment. Ultimately, they're all designed to break the ice and help you peel back the layers as you explore whether this relationship is sustainable.

You should ask these questions directly as that will obviously lead to the best and most natural conversation, but you can also use texting.

Fun Questions to Ask a Guy

1. Do you want a month-long home stay or a week-long adventure?
2. If you could meet any hero, who would you choose?
3. What would your last meal be?
4. How many meals do you usually eat a day?
5. Which fictional character would you like to see come true?
6. Which celebrity would you like to switch roles with?
7. What superpower do you wish you had?
8. What is the worst movie you have ever seen?
9. Which movie villain do you think is the most misunderstood?
10. What skill would you choose if you knew you could master it in a year?
11. What does your ideal Sunday look like?
12. What is your favorite animal?
13. Do you drink tea or coffee?
14. What is the craziest thing you have ever seen?
15. Who do you want to tell your life story to?
16. What is your most surprising talent?
17. What is your favorite movie?
18. What position do you sleep in?
19. Which type of potato is best?
20. What is your favorite item in your wardrobe?
21. Are you an early bird or a night owl?
22. What is your favorite holiday?
23. If you could be any animal, which one would you choose to be?
24. What is the greatest invention of all time?
25. What is the best costume you ever wore for Halloween?
26. How many alarms do you set in the morning?
27. Chocolate or candy?
28. Mustard or ketchup?
29. What is something illegal that you think should be legalized?
30. What is one thing you would never waste money on?
31. What would you do if money was no object?
32. What did you want your job to be when you were a child?
33. Would you adopt a dog or a cat?
34. Do you remember your dreams?
35. What do you look forward to each year?
36. What is your favorite meal?
37. What is the best pizza topping?
38. If you had to choose one song to listen to over and over again, what would it be?

1. Which animal would be the worst - and most surprising - to trap you in a room with?
2. What was the best trip you ever had?
3. Do you like it cold or hot?
4. What is the best concert you have ever attended?
5. What flavor of sparkling water do you like?
6. What is the most underrated place you have ever been to in your travels?
7. Crunchy or creamy peanut butter?
8. What annoys you the most?
9. What purchases have you regretted recently?
10. What's your favorite guilty pleasure podcast?
11. Is Friday or Saturday a better day of the week?
12. Is there a hairstyle you've always wanted to get but were afraid to try? Do you prefer showers or baths?
13. When was the last time you stayed up all night?
14. If you could choose a mascot to represent yourself, what would you choose?
15. If you could give yourself a new name, what would it be?
16. What is your favorite karaoke song?
17. If you could get on a plane and go anywhere right now, where would you go?
18. What is your signature breakfast dish at a restaurant?
19. Is there any world record you think you can break?

Isabella Humphrey

Update 25 July 2025