Ask A Guy A Question: 183 Genius Ideas For In-Person/Over Text Conversations That'll Keep Him Talking

*This post will help you ask a guy a question*

Want to ask a guy a question but not sure what to ask? No worries. I have over 100 super engaging questions you can ask your guy in person or over text that’ll keep him chatting.

These questions have personally helped me make tons of guy friends during my first few months of college and helped me get and keep the attention of my then crush, now husband, Ro-Jay (who I also met while in college).

As such, I know these questions will help kickstart a never-ending conversation full of laughs and intimacy! More importantly, these questions will give you insane insight on who your guy is, what he’s about, and what he cares/doesn’t care about.

These questions include:

Personal questions to ask a guy
Questions to ask a college guy
Flirty questions to ask a guy
Random questions to ask a guy
Questions to ask a guy over text
Weird questions to ask a guy, and
Would you rather questions for your crush (My personal favorite 😉 )

If you’re ready, I’m ready! Let’s jump in!

Personal Questions To Ask A Guy

I think it’s fair to say that if you’re gonna ask a guy a question, especially to someone you just met, that start asking some personal questions first. And if you’ve known your guy a while then…what are you waiting for? Asking the personal stuff is a great natural way to get a conversation going that has the potential to go in 100 million different directions. My advice, is to start with the softball questions and if you’re feeling bold, go hardball (*)!

Here are the best personal questions to a guy:

1) What is your hometown?

2) Where did you grow up?

3) What is your ethnicity?

4) What is your religious or spiritual affiliation?

5) Do you have any siblings? If so, how many?

6) Are you the eldest or are you the baby in your family?

7) What’s your middle name?

8) Do you speak more than one language?

9) What countries have you visited?

10) What are your hobbies?

11) What is the most embarrassing thing you’ve ever done?

12) What is the wildest thing you’ve ever done?

13) What are your strengths?

14) What are you most insecure about?

15) What’s your favorite childhood memory?

16) What’s one thing you wish you could change about yourself?

17) What is your favorite holiday?

18) Are you close to your parents? If so, who are you closest to?

19) What do your parents do for a living?

20) What is your diet? (Are you vegan, vegetarian, meat-eater)

21) Do you have any regrets in life? If so, what do you regret?

22) If you could have a do-over at life, what would you do-over?

23) What is the most trouble you’ve ever gotten yourself into?

24) What is the worst/funniest prank you’ve ever pulled?

25) Do you have any pets?

26) What animal or insect are you most afraid of?

27) What is the most expensive thing you own?

28) Have you ever had a near to death experience? If so, what was it?

29) Who is your favorite superhero?

30) Who is your favorite Actor?

31) Who is your favorite actress?

32) What was one fear you had as a child that you no longer have as an adult?

33) Do you smoke or drink?

34) Do you have a criminal record? **

35) What’s your sexual orientation? * / **

Ask A Guy A Question: College Edition

Okay, so these questions are totally responsible for the tons of guy friends I made in college. And If you’re in college, these questions without fail will help you make tons of guy friends in college too! No matter who you talk to, guys will readily and willingly answer these questions because they’re in college! They expect it and love it. And like personal questions, these are excellent gateway questions that have the potential to go into 100 different directions too! Have fun with these!

36) What is your major?

37) What year are you?

38) What experience are you most excited to have here at college?

39) What do you love most about college?

40) Are you a part of any clubs? (or what clubs are you interested in joining?)

41) Are you an early bird or a night owl?

42) Was this school your first choice?

43) What brought you to this school?

44) What classes are you taking this semester?

45) If you couldn’t major in x, what would you major in?

46) If you couldn’t attend college, what would you do?

47) Do you prefer studying at home or the library?

48) What is your favorite sport to watch?

49) Do you live on campus or off?

50) If you won a scholarship to study abroad anywhere in the world, where would you go?

51) If you could automatically get into any school, tuition-free, where would you go?

52) If you had to study a language, which language would you study?

53) If you had to go to trade school instead, what would you take up?

54) What is your learning style? (Visual, Auditory, Kinesthetic, Reading/Writing)?

55) What is your favorite subject?

56) Do you miss anything about high school?

57) What is your greatest memory from high school?

58) If you could do over anything in high school, what would it be?

59) What type of music do you enjoy listening to?

60) What is your GPA?*

61) Are you in a fraternity or are you interested in rushing?

Flirty Questions To Ask A Guy

Looking for some good flirty questions to ask a guy? These questions are up your alley! These questions will for sure give your guy butterflies (yes they get them too), make their heart race, make their cheeks red and warm, but at the very least get their heart pumping and ear and eyes perked up!! By the way, these questions are also equally good questions to ask a guy over a text, so if you’re feeling shy, don’t hesitate to take out your phone.

62) Who was your celebrity crush growing up?

63) Who is your celebrity crush now?

64) If we were stranded on an island (just the two of us) what would you want to do first?

65) If I went into your car right now and turned on the radio, what would be playing?

66) Confess: Have you ever gotten a professional mani/pedicure?

67) How often do you work out?

68) Do you find me attractive?

69) If so, what is the most attractive thing about me?

70) How long do you think you would last on Survivor if called to be on the show?

71) If you had to Audition for America’s Got Talent, what would be your talent?

72) What’s the heaviest you can lift?

73) Can you dance?

74) What does a perfect date look like for you?

75)Are you dating anyone?

76) How many relationships have you had?

77) What makes you feel most respected?

78) What makes you feel most loved?

79) What do you look for in a girlfriend?

80) What is a dealbreaker for you in a relationship?

81) When would you get married?

82) If you could live anywhere, where would you live?

83) Do you like me?

84) If so, what do you like most about me?

Random Questions To Ask A Guy

Okay, now we’re building momentum! Below, you’ll find tons of great random questions to ask a guy that will help you get to know your guy a WHOLE lot better. You’ll learn about their pet peeve, their favorite foods, and most importantly, if they are team iPhone or team Android (because that’s, like, really important lol).

85) What are your pet peeves?

86) Do you have a talent? If so, what is it?

87) What’s your favorite color?

88) What is your favorite movie of all time?

89) What is your favorite Disney movie?

90) Do you like roller coasters?

91) Can you cook?

92) Do you have any weird habits?

93) What is your favorite book?

94) What is your favorite TV show?

95) What is your favorite song?

96) What is your favorite sport?

97) Do you actively play any sports?

98) What is your favorite exercise?

99) What food tempts you the most?

100) What is your favorite cuisine?

101) What cuisines have you not tried that you are interested in trying?

102) What cuisine do you like the least?

103) Have you ever won a trophy for anything in your life? If so, what was it for?

104) What is one thing you’ve done that you’re most proud of?

105) Do you pass your driving test the first time? If not, why?

106) Have you ever gotten pulled over by the police? If so, what was the reason?

107) What is the worst sickness you’ve ever come down with?

108) Who is your favorite superhero?

109) Who is your favorite Actor?

110) Who is your favorite actress?

111) What country are you dying to visit?

112) What turns you off about a girl?

113) What turns you off about a guy?

114) Can you float?

115) Have you ever broken a bone? If so, which one and how did it happen?

116) Do you know how to swim?

117) What is the farthest you can run without stopping?

118) Are you team iPhone or Android?

119) How many phones have you owned in your lifetime?

120) What is one sport you’ve never tried that you’re dying to try out?

121) If you could only eat one cuisine for the rest of your life, what would you eat?

122) If you had to be stranded on an island, which island would you pick?

123) What social media platform do you use the most?

124) What was the last thing you ate for breakfast?

125) How much money do you want to make?

Questions to Ask A Guy Over Text

If you’re like me, there are just some questions that you won’t have the guts to ask a guy in person because you either don’t want him to hear your heart racing, you’re afraid to see/hear his reaction, or you want to make him answer the question thoughtfully and directly… Yeah, texting is the way to go. Here are some excellent questions to ask a guy over text that I think your guy will also be thankful you’ve asked over text.

126) Are you single or dating?

127) If you’re dating, how long have you been in a relationship?

128) How many relationships have you had?

129) Do you find me attractive?

130) What is most attractive about me?

131) Do you like me?

132) What do you like most about me?

133) Your circle of friends is made up of mostly which sex? Girls or guys?

134) On a scale of 1-10, how clean is your room?

135) Have you ever been in love?

136) Are you a virgin?

137) What is your love language?

138) How do you receive love the most?

139) Do you watch porn? *

140) Do you struggle with anything or have any addictions? *

Weird Questions To Ask A Guy

Want to dish out some weird questions? Can your guy handle you being weird for a few minutes? If so, here are some weird questions to ask a guy that will definitely get your guy thinking “weird question..but okay. Um—”

141) Do you have any weird habits?

142) Do you bite your fingernails?

143) Do you eat with your mouth closed or open?

144) Do you talk or snore loudly while your sleep?

145) Do you sleep on the left or right side of the bed, and why?

146) What gives you the creeps?

147) Are you allergic to anything?

148) What is the most disgusting insect you’ve touched or held in your hands?

149) Do you shower with a washcloth or bath sponge?

150) Do you shower with bar soap or a bottle of body wash?

151) When did you start growing manly hair?

152) When did you begin shaving?

153) Who has the weirdest name in your family and what is their name

Would You Rather Questions

I saved the best for last! Below are tons of insanely good “Would You Rather” questions for your crush (or anyone ). There is no way your guy and you are coming out the end of these questions without some serious laugher and some fun, but heated protests!! Have fun with these!!!

154) Would you rather read a book or watch TV?

155) Would you rather live in the city or the suburbs?

156) Would you rather have summer or winter?

157) Would you rather shop at Walmart or Target?

158) Would you rather eat out at a restaurant or eat a home-cooked meal?

159) Would you rather have Vanilla or Chocolate?

160) Would you rather watch a scary movie or a drama?

161) Would you rather start a business or have a career (job)?

162) Would you rather eat ice cream or pizza?

163) Would you rather face a hurricane or an earthquake?

164) Would you rather take Uber or Lyft?

165) Would you rather wear Jordans or Yeezys?