Sometimes, it can be difficult to know what to ask a guy you like over text. It’s important to ask about things that can be easily expanded on and lead to a fun conversation. These questions to ask a guy over text are perfect for getting to know someone better. They can be used whether you’ve been on a first date or not.
If you’re in an established relationship, you can also use these questions to ask your boyfriend over text to spark an exciting discussion. It’s easy to send messages like ‘what’s up?’ But they are bland and boring. So if you want to know what to talk about with a guy over text, this list is for you!
Table of Contents
Best Questions To Ask A Guy Over Text

1. What movie could you watch repeatedly and never get bored?
2. Tell me what your perfect weekend looks like?
3. Would you ever go on a reality show to meet new people?
4. What’s the most embarrassing thing you have ever done in front of your crush?
5. What crime would you commit if you knew you would get away with it?
6. If you could invite anyone, dead or alive, for a beer, who would it be and why?
7. What five words would your friends use to describe you?
8. Tell me the most awkward or funny line you’ve ever tried to start a conversation with?
9. What’s been the funniest thing that’s happened to you this week?
10. What’s the most embarrassing thing you’ve bought off the internet?
11. What are the top 5 things on your bucket list?
12. When you’re looking for a relationship, what qualities do you look for in a person?
13. How long ago were you last in a relationship?
14. Do you have a specific type of person you usually connect with?
15. If you could have any superpower, which one would it be and why?
16. If I could take you to any restaurant on a date, where would you like to be taken to?
17. What’s the most embarrassing text you’ve sent to the wrong person by mistake?
18. What memory from childhood do you think had the most significant impact on your life?
You might also like:
- Funny questions to ask a guy
- Random questions to ask a guy
- Questions to ask a guy to know his intentions

19. Do you think you’re more of an introvert or an extrovert?
20. If money were no object, where would you want to live in the world?
21. Do you know any facts that, if more people knew, they would be completely shocked?
22. Do you think people can fall in love at first sight?
23. What was your favorite childhood movie?
24. What pet peeves do you have?
25. Do you have any hidden talents?
26. What’s your favorite movie quote?
27. Tell me the most random piece of trivia you’ve learned?
28. What was the last music concert you went to?
29. What’s the most memorable gift you’ve ever received?
30. Is there an extreme sport you’d like to try?
31. Which celebrity have you got the biggest crush on?
32. When did you last do something that was entirely out of your comfort zone?
33. When did you last laugh so much you cried?
34. What’s your favorite late-night snack?
35. What’s your favorite fast-food joint?
36. Do you like reading?

Next: Juicy questions
37. What book has had the most significant impact on your life, for better or worse?
38. When did you last say something you later regretted?
39. When was the last time you hurt someone’s feelings?
40. What’s the worst joke you’ve ever heard?
41. How would your friends describe you?
42. What daydream do you think of when you’re bored?
43. What sort of comedy do you like?
44. What lousy habit can you not stand?
45. What time of the year is your favorite?
46. What’s the worst date someone could take you on?
47. What are the main traits you look for in a partner?
48. What’s the biggest life lesson you have learnt?
49. Have you ever used apps to meet new people? What was your experience?
50. Do you think there’s any such thing as soulmates?
51. What’s your most-used emoji on your phone?
52. Where have you always wanted to travel to?
53. What GIF or video on the internet is always guaranteed to make you laugh?
54. What restaurant would you most likely order a takeaway from?

55. What music album could you play on repeat?
56. Which song do you think has the best introduction?
57. What’s the weirdest text you’ve ever received?
58. What’s something you have near you now that has an interesting story attached to it?
59. What app would you recommend anyone get?
60. Show me the best photo ever taken of you?
61. Is there anything you wish you could buy yourself right now?
62. What’s the funniest picture on your phone right now?
63. What’s been your most memorable life experience?
64. What are some unwritten rules when it comes to being in a relationship?
65. What happens in relationships that the movies never portray?
66. Tell me something that isn’t real, but you wish it were?
67. What’s something silly that you’re massively passionate about?
68. How long do you think you could make it without your phone?
69. What’s the most shocking thing you’ve seen on the internet recently?
70. What food is always worth the calories?
71. What’s your favorite place to take someone to hang out?
72. Have you ever checked up on someone from your past on social media?
Next: Questions to ask a guy
73. What’s something most people can’t do but you can?
74. Say something right now in emojis, and I must guess what you’re saying.
75. If you had to give up sight or hearing, which would it be and why?
76. Do you have any weird likes or dislikes?
77. Starting when you wake up, tell me your idea of the perfect day?
78. Do you think you could answer the following ten questions I ask you in only pictures?
79. What do you miss most about childhood?
80. What life moments have made you into the person you are today?
81. What in your life so far do you think was worth the wait?
82. What’s something in life that’s your kryptonite?
83. What’s been the best car you’ve ever owned?
84. Is there a question people ask you a lot that you wish they wouldn’t?
85. What always cheers you up when you’re in a bad mood?
86. What’s your worst habit?
87. What TV series can you always have on in the background, even when you’re trying to concentrate?
88. What current trend can you not get your head around?
89. What’s something you’ve done that not many people have done?
90. Have you ever been on TV?

You might also like: Flirty questions to ask a guy
91. What’s your perfect summer day?
Deep Questions To Ask A Guy Over Text
92. How do you feel about commitment?
93. Who out of your friends are you most jealous of?
94. Do you want to have any children one day?
95. What’s one thing that can help you decide whether you trust someone?
96. What fears do you have about getting into a relationship?
97. Have you ever been tempted to break someone’s trust?
98. Have you ever been deeply affected by someone you cared about?
99. What’s one thing you would never say to someone you had a crush on?
100. What in life brings the most joy and happiness?
101. Is there anything from past relationships you’ve learned but don’t talk about much?
102. Do you believe people can make a success out of long-distance relationships?
103. Describe what a healthy relationship looks like to you.
104. Do you think we could have a meaningful connection over time?
105. What’s the best relationship advice you would pass on to anyone looking for love?
106. What’s your approach when dealing with conflict?
107. Could you ever forgive someone who seriously broke your trust?
108. How do you think partners should support each other through big life changes?
You might also like: Deep questions to ask a guy
109. What’s the biggest mistake you’ve made in a past relationship?
110. How do you find single life?
111. What’s your opinion on splitting the bill?
112. Do you think it’s essential to be married before you have children?
113. Do you think a significant age gap matters in a relationship?
114. Have you got any doubts about whether we would make a great couple?
115. What person in your life has had the most significant impact on you?
Intimate Questions To Ask A Guy Over Text
116. What was the first thing you noticed about me?
117. What qualities do you find most attractive in a person?
118. Have you ever bought a thoughtful gift for someone you liked?
119. What kind of gift do you think suits me?
120. What’s a dream you remember clearly or found interesting?
121. Have you ever dreamt about someone you know?
122. Are you more of a leader or a go-with-the-flow type of person?
123. What’s one thing that can instantly put you off someone?
124. Have you ever walked away from a girl you still had strong feelings for?
125. Have you ever tried something new in a relationship just for fun?
126. Have you ever had a very short-lived connection with someone?
Next: Personal questions to ask a guy
127. How do you feel when someone makes the first move?
128. How do you feel about showing affection in public?
129. Is there something meaningful you’d like to experience with someone but feel shy bringing up?
130. Have you ever had a relationship that didn’t fit the traditional label?
131. How do you feel about mixing fun activities in unexpected ways?
132. Do you enjoy playful banter?
Fun Questions To Ask A Guy Over Text
133. If you were a girl for a whole day, what would you do first?
134. Tell me one of the strangest things on your bucket list.
135. What’s your number 1 guilty pleasure?
136. Who was the last person you tried to impress?
137. What do you usually wear when you’re relaxing at home?
138. Do you enjoy making small talk with people you don’t know?
139. What style of clothing do you think looks great on people?
140. If you could teach women a lesson about how to deal with men, what would it be?
141. What’s your favorite activity to do on a date?
142. Do you think intense relationships are healthy or exhausting?
143. Have you ever stopped talking to someone without explaining why?
144. Has anyone ever made you uncomfortable by paying too much attention to you?
145. Would you rather spend a weekend with friends or with someone you’re close to?
146. How long does it take you to get ready in the morning?
147. What’s the worst sleeping habit a girl could have?
148. Have you ever sent a girl a love letter?
149. How much effort do you think is reasonable when pursuing a relationship?
150. Have you ever been caught in a really awkward or embarrassing situation?
Looking For More Questions?
Questions girls are afraid to ask guys – The questions you’ve always wanted to ask the guy in your life!
Flirty questions to ask your crush – If the guy you’re texting is your crush, some of these questions might be useful.
Online dating questions – Great questions to ask when speaking with someone online and to freshen up the conversation.

