Flirty, Funny, and Deep Questions to Ask Your Boyfriend or a Guy You Like

Witty and unique questions to keep a guy interested while texting

Co-authored by John Keegan and Hannah Madden

Last Updated: November 29, 2024 Fact Checked

So, you’re texting a guy, but all you can think to ask is, “Wyd?” While updating each other on your daily routines is totally fine, it does tend to get a little boring after a while. That’s where we come in: we’ll give you the best funny, flirty, and deep questions to ask a guy over text so you can keep the conversation going all day long. Whether he’s your boyfriend, your crush, or just a friend, you’ll never run out of things to talk about with our handy list.

Things You Should Know

Ask him questions about his personality to get to know him better, like if he has any hidden talents or if he likes horror movies.
Get silly by asking questions about his most embarrassing moment or his favorite joke of all-time.
Try some serious questions to make the conversation more intimate, like asking him about his childhood memories.
Flirt with him over text by asking if he’s okay with PDA or if he’s crushing on anyone right now.

Section 1 of 1:

Question to Ask a Guy Over Text

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2
How do you usually spend your weekends?

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3
Do you have any hidden talents?
4
What’s one of your oldest memories?
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6
Do you have any pet peeves?
7
What’s the funniest text you’ve ever gotten?
8
Coffee or tea?
9
Did you ever have an imaginary friend?
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11
What would you do if you only had 24 hours to live?
12
Are you a morning person or a night owl?
13
What is your least favorite food?
14
If you could only eat 1 meal for the rest of your life, what would it be?
16
What’s the biggest lie you’ve ever told?
17
What’s your worst habit?
18
Who’s your celebrity crush?
19
What is your favorite quality about yourself?
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21
What did you want to be when you grew up?
22
What’s your favorite dessert?
23
Do you collect anything?
24
What’s the weirdest thing on your bucket list?
26
What’s one of your most embarrassing moments?
27
What’s your go-to video when you need a laugh?
28
What’s your best joke?
29
What’s the best WiFi name you’ve ever seen?
31
Do you hang your toilet paper over or under?
32
What would you do if you could live forever?
33
Pineapple on pizza: yes or no?
34
What’s the weirdest thing you’ve seen a stranger do in public?
36
Have you ever fallen asleep during class?
37
If animals could talk, which species would be the rudest?
38
What’s the most creative insult you can think of?
39
If you were a girl for a day, what’s the first thing you would do?
41
What’s your greatest accomplishment in life so far?
42
What do you value most in a friendship?
43
Do you believe in giving people second chances?
44
What’s your star sign?
46
Are you close to anyone in your family?
47
What are your passions in life?
48
What’s your favorite way to relax?
49
Who inspires you?
51
If you could redesign society, what would you change?
52
Do you believe in marriage?
53
Do you want to have kids?
54
When was the last time you cried?
56
What are your major goals in life?
57
Do you prefer being single or in a relationship?
58
What’s your favorite type of kiss?
59
What’s your favorite pickup line?
61
Do you have a crush on anyone right now?
62
Would you rather be the big spoon or the little spoon?
63
What physical feature do you find most attractive?
64
Do you believe in love at first sight?
66
How do you feel about kissing in public?
67
When’s the last time you felt butterflies?
68
What’s your idea of a perfect partner?
69
If I could take you out right now, where would you want to go?
71
What 3 qualities are you looking for in a partner?
72
Do you have any terrible first date stories?
73
What’s your idea of a perfect date?
74
Do you prefer cuddling or making out?
75
What are the signals you give someone when you like them?

Join the Discussion...

What are questions guys love to be asked?

David Chambers
Dating and Relationship Coach

What do you really enjoy doing that you don't always find the time to do?
What’s the most fun you’ve had in the last few months?
What’s something people often misunderstand about you?
Who’s someone you really admire and why?
If you could invite anyone in the world to dinner, who would it be?