Get the Conversation Flowing With Match’s Top Picks of Questions To Ask a Boy

Get the conversation flowing with these questions to ask a boy you like. Have some fun, get to know him and spark some interesting conversation!

It can be scary talking to someone new for the first time, especially when you’re trying to establish a more meaningful connection. Everyone wants to get to the point where the conversation is flowing as easily as the wine – but getting there can be a challenge!

Well, fear no more; Match is here to get you started with 70 questions to ask a boy you like. Use these date questions to have some fun, get to know him and spark some interesting conversation.

Don’t forget that the aim is to get to know one another, not to interrogate him or scare him off, so keep things lighthearted and try not to ask anything which might seem intrusive or nosey. You’ll learn everything about him in due time if you’re supposed to!

Your best bet is to ask open-ended questions that can lead to discussion but aren’t too broad that he won’t know where to start.

You don’t have to have it all worked out – treat these questions to ask a boy as conversation starters to get to know him a little better. Great conversation is all about listening, connecting and being yourself!

First Date Ice-Breaker Questions

The first date’s on the cards. You’ve got all dressed up, sent the “I’m on my way!” message and remembered to take your keys. You’re good to go! Except… what do you say when you finally meet face-to-face?

We find it helpful to have some fun conversation starters or quirky questions to ask your date to warm them up and dispel any awkwardness so you can focus on getting to know each other.

Here are some questions to ask a boy to get them chatting, have a laugh and learn a little more about them:

1. Are you close to your family?
2. Do you have any pets?
3. Tell me about your best friend.
4. If you ran into the prime minister in a lift, what would you say?
5. What is your favourite place you’ve travelled to?
6. Would you ever get naked in public?
7. What’s the coolest thing you’ve ever done?
8. What’s the first album you bought/the first gig you went to?
9. What was the last book you read?
10. What’s the worst job you’ve ever done?
11. What TV show are you currently streaming?
12. What show did you binge watch?
13. What’s your go-to karaoke song?
14. Who was your childhood crush?
15. Do you have a party trick?
16. Do you like dancing? When was the last time you danced like no one was watching?
17. If you could live in another country tomorrow, where would you choose?
18. Which actor would play you in a film about your life?
19. What’s your biggest guilty pleasure?
20. Who would you invite to your dream dinner party and why?

Questions About Their Hobbies and Interests

A fulfilling dating journey often starts with connecting over a shared interest, passion or way of seeing the world. If you’ve met on Match, the chances are you already know some of the things they’re into from their profile, so now it’s time to dig a bit deeper with our questions to ask a boy about their hobbies and interests.

21. What do you do in your spare time?
22. Do you have any passions?
23. Do you play or follow any sports?
24. If you had more time, what hobby would you like to pick up?
25. What’s something you’ve done that you’re proud of?
26. Do you prefer the indoors or the outdoors?
27. How do you unwind after a stressful day?
28. Do you hang out with your friends a lot? What do you do when you see them?
29. Do you know how to play any instruments?
30. What kind of music do you listen to?
31. What’s on your bucket list?
32. Do you consider yourself a foodie? What would be your dream meal?
33. What’s something you like that people don’t expect from you?
34. Do you like to travel? Where would you most like to visit?
35. What’s something you’ve always wanted to do but haven’t yet?

Questions About Who They Are and How They See the World

So… the date’s going well. The conversation is flowing, you’re laughing and learning more about each other. It might be time to scratch a little below the surface and learn a little more about who they are on a deeper level. Our questions to ask a boy about who they are and how they see the world will help you build intimacy and see if your values are aligned.

Remember, some of these questions are a little personal, so respect his boundaries and only ask them if the conversation is headed that way. You might even want to save them for the second or third date, once you’ve established your connection a little better.

36. What expectations do you have of yourself?
37. What do you expect of someone else?
38. What is your favourite thing about yourself?
39. If someone made a TV show about your life, what would the theme song be?
40. If you could commit a crime and never get caught, what would it be?
41. Would you rather make more money doing a job you dislike or less money doing a job you love?
42. If you could go back in time, what would you tell your 19-year-old self?
43. How do you measure success?
44. What has been your biggest inspiration?
45. What were some of the turning points in your life?
46. What’s getting worse and worse as you get older?
47. What’s getting better and better as you get older?
48. Do you consider yourself more of an introvert or an extrovert?
49. Who besides your parents taught you the most about life?
50. What would you do tomorrow if it was your last day on earth?
51. What qualities do you value in a friend?
52. What’s the biggest risk you’ve ever taken?
53. If you could do any job in the world, what would it be?
54. What makes you happy?
55. What makes you sad?

Questions About Dating and Love

Dating is all about building a romantic connection, so understanding their approach to love and relationships will be important in seeing whether you want to continue getting to know him. You should keep things light early on so as not to put too much pressure on him, but that doesn’t mean you can’t find out a little more about his approach to love.

These questions to ask a boy about dating and love will help you get to know him on a more romantic level while keeping things a little flirty!

56. Describe your dream date.
57. What’s the best chat-up line you’ve ever used?
58. What qualities do you look for in a girlfriend?
59. Do you have any children? If not, do you want any?
60. What would you cook on a date?
61. What’s one thing you wished women understood better about men?
62. What’s your biggest dating fail?
63. Have you ever been in love?
64. What’s the most romantic thing you’ve ever done for someone?
65. What song would you play to impress a girl?
66. First dates… fun or scary?
67. Who do you go to for girl advice?
68. What made you want to sign up to a dating site?
69. Have you ever had your heart broken?
70. What’s the most adventurous date you’ve ever been on?

Now you’re ready for a fun date and some awesome conversation! Just remember, having a script for a date isn’t the most natural way to get to know someone – these questions are simply there to give you a little helping hand.

Try not to overthink it and just go with the flow – once the conversation has found its groove, asking these questions will probably be the last thing on your mind…

Read more of our expert dating advice and begin your dating journey by registering for Match for free today!