Questions to Ask a Guy: 110 That Get Him Talking

Questions to ask a guy to get to know him

There's no secret set of questions for men. Everyone on Natter is 18+, so ask him what you'd ask any grown-up you found interesting, then listen for what lights him up. These suit the first few chats.

1. What does a normal weekday look like for you, from alarm to bedtime?
2. Who's the first person you text when you've got good news?
3. What do you do on the first warm day of the year?
4. Which day of the week is secretly your favourite, and why?
5. What's a question you always get asked about your job?
6. How did you end up living where you do now?
7. What's your Sunday-night routine?
8. Where do you do your best thinking?
9. What's your idea of a properly productive day?
10. What's a meal that always reminds you of someone?
11. What do you do for work, and is it what you pictured doing?
12. What were you doing this time last year?
13. What's something you taught yourself to do?
14. What's a goal you're working towards this year?
15. What would your perfect neighbourhood have in it?
16. How would your closest mate describe you in three words?
17. Which of your habits drives the people you live with up the wall?
18. Where did you grow up, and what do you miss about it?
19. What are you looking after at the moment: plants, pets, a project?
20. What's a small thing you always notice that other people miss?

Questions to ask a guy over text

Messages have their own rhythm. He might be on a bus, at work or half-watching something, so these are short and easy to answer between other things. On Natter they work just as well in private messages, and there's no rush to move the chat anywhere else: keep it on the site until you've met and feel sure. For more on messaging well, see the how to chat guides.

39. What's the most useful thing you've done today, and the least useful?
40. What song's been stuck in your head this week?
41. What's the story behind the last photo you took?
42. What's the most random thing you've looked up online this week?
43. What's one thing you'd do this weekend if the weather behaved?
44. What's made you nostalgic lately?
45. What happened today that you wish you'd had someone to tell?
46. What's the nicest message you've had this week, apart from mine?
47. What's a small treat you've got lined up for later?
48. What's the funniest thing you've overheard lately?
49. What's a tab you've had open on your browser for far too long?
50. If today had a title, what would it be?
51. Which of your mates would you trust to plan your holiday?
52. What's your texting style: instant replies, or long ones hours later?
53. What's the oldest message on your phone you still haven't replied to?
54. What can you hear right now, apart from your own typing?
55. What's something you saw today that you think I'd like?
56. What's the joke doing the rounds in your group chat this week?

Deep questions to ask a guy

These are for a quieter evening when you've both got time to think. Go first if you can, so he sees you're not asking for anything you wouldn't give, and let him skip any he isn't ready for.

75. Who would you call at three in the morning, no questions asked?
76. What would you tell someone who's just had their heart broken?
77. When was the last time you changed someone's mind, or they changed yours?
78. What's a dream you've let go of, and how do you feel about it now?
79. What's something you'd like to be braver about?
80. What does a good apology look like to you?
81. What's a conversation that changed how you see things?
82. What's a fear you've faced, and how did it go?
83. How have you changed in the last five years?
84. What do you value more now than you did a few years ago?
85. What do you think makes a relationship last?
86. Is there something you wish you'd said to someone, and still could?
87. What helps you through a rough week?
88. What's something you believe that most people around you don't?
89. What does a life well lived look like to you?
90. How do you handle disagreements with people you care about?
91. What part of your day do you guard most closely?
92. What are you most grateful for right now?

Questions to ask a guy on a first date

Face to face, you've got smiles, tone and pauses to work with, so these can be more relaxed. You won't need many: three or four good ones and plenty of listening make a lovely evening.

93. How does tonight compare with the chats we've had?
94. What would you normally be doing on a night like this?
95. What's your usual order at a place like this?
96. What's a story your friends always make you tell?
97. What's a small adventure you've had lately?
98. Which of your friends would you want me to meet first, and why?
99. What's the nicest thing a waiter or barista has ever done for you?
100. What do you think this place is like on a Monday morning?
101. What was the highlight of your week, before tonight?
102. What's a small thing you do for yourself every week?
103. What turns an ordinary night out into a great one?
104. What do you think makes a good first date?
105. Who's the most interesting person you've ever met?
106. Which three songs would be on the soundtrack of your year?
107. What's the funniest thing that's happened to you on a night out?
108. Darts, pool or cards: which would you beat me at?
109. Who's the friend who'll want a full report on tonight?
110. If we did this again, what should we do next time?

Before you go, the sensible bits: meet somewhere busy and public, tell a friend where you'll be, and sort out your own way there and home. If anything feels off, you can leave whenever you like. There's more in our chat safety guide.