217 Of The Best Flirty Questions To Ask A Guy

Have you ever tried to flirt with your crush but found yourself tongue-tied?

Or maybe you’re looking for ways to get to know your boyfriend a little better.

Either way, this list of flirty questions to ask guys will open up doors in your relationship, no matter what stage you’ve reached. 

Asking these questions can help you gain a deeper understanding of him as a person while also developing your bond.

Knowing him better will give you a new appreciation for his strengths and a better understanding of his point of view. 

The only downside is you’ll wonder why you didn’t read this sooner.

What Are Good Flirty Questions? 

Before you dive into the lists of flirty questions to ask a guy, let’s spell out the qualities that make a particular flirty question worth asking: 

  • It’s easy for the guy in question to answer; 
  • It makes the guy feel more interesting; 
  • It fits the occasion and gives you both something to talk about;
  • It gives you a sense of a guy’s patience with random questions;
  • It distracts you both from the awkwardness (and doesn’t add to it); 
  • It gives you a chance to build and practice confidence; 
  • It reveals useful information about his character and preferences. 

The best flirty questions will get you the information you seek without giving too much away.

Do it right, and there’s a strong chance the guy in question will ask you those questions right back and show an interest in your answers. 

Related: 105 Good Morning Messages for Him to Start His Day

217 Flirty Questions to Ask a Guy

Ready to get started? Grab a pen and paper and write down your favorite questions.

Or better yet, print this entire article and keep it handy so you can surprise your guy with a new question every day.

Cute Flirty Questions to Ask Your Boyfriend

Just because he’s your boyfriend doesn’t mean you already know everything you need to know about him.

And these cute flirty questions to keep it light while you learn useful information about each other. 

1. When did you know you liked me? Where were we/What were we doing at the time?

2. What’s your idea of a perfect date? Where would we go? What would we do?

3. What is your love language?

4. What does love mean to you? How do you know someone loves you?

5. What color do you think I look best in? What style of clothing?

6. What song would you compare our relationship to?

7. What was your favorite part of the day today?

8. Where do you feel safest? Is there a person you feel most comfortable with?

9. What was your first impression of me?

10. What’s your favorite activity to do to unwind or relax?

11. What’s your favorite memory that we shared?

12. What couples activity would you like to try? Ex: Couples yoga, crafting challenges, etc.

13. What three words would you use to describe me?

14. If we had to spend the day together in one place, where would we go?

15. Do you like using pet names? Are there any in particular that you prefer?

16. What’s your funniest childhood memory?

17. What’s one word that you’ve noticed me using excessively? Are there any words that you tend to overuse?

18. Name three things that never fail to make you smile.

19. What’s something you could talk about forever? What topic are you most passionate about?

20. Do you prefer kissing or hugging?

21. What’s the biggest deal-breaker in a relationship?

22. What’s your favorite mindless activity? Ex: Coloring, Watching TV, Reading, etc.

23. What’s your favorite grounding activity? Ex: Yoga, Meditation, etc.

Flirty Questions to Ask a Guy You Like

If you like this guy, and he’s willing to answer some questions, the following will give you a peek into the way his mind works — as well as whether he’s into you, too (though you might have to rely on body language for that). 

24. What’s your favorite TV or book couple?

25. What, in your opinion, is the best feel-good song?

26. Who knows you better than anyone?

27. If you could be a master of any one skill, what would it be?

28. What’s the nicest thing someone could say to you?

29. What accomplishment are you most proud of?

30. What’s something that not many people know about you?

31. Do you believe in love at first sight? Why or why not?

32. Do you prefer movie dates or restaurant dates?

33. What makes you laugh?

34. Do your friends have any nicknames for you? Do you like them, or would you like to change them?

35. Do you prefer a sweet breakfast or a savory one? What foods do you like to start your day with?

36. Do you like big romantic gestures or simple ones?

37. When something good happens, who’s the first person you want to tell?

38. If something bad happens, who do you confide in?

39. What’s your favorite kind of pie? Who makes the best?

40. Do you like to keep your birthday simple, or do you like to throw a party?

41. Do you like spicy food? What’s the spiciest thing you’ve ever tried?

42. How do you like your eggs? What foods do you like to combine them with?

43. If you could be famous, what would you want to be famous for?

44. What was your favorite extracurricular activity in school?

45. What’s your zodiac sign? Does your personality reflect your sign?

46. What’s your favorite board game?

More Related Articles:

77 Questions To Ask Your Significant Other For A Closer Connection

23 Signs A Guy Is Really Into You

What Does It Mean When Your Girlfriend Calls You Daddy?

47. If you had $500 to spend on anything, what would you do?

48. Which fictional character do you most identify with?

Fun Flirty Questions to Ask a Guy

Picture yourself just having a fun conversation with a guy, and suddenly, your mind goes blank. And now he’s giving you that dreaded questioning look. That’s why it’s good to keep fun questions like the following handy.  

49. Are you a roller coaster person or a ferris wheel person?

50. If you could live in any fictional world, which would you choose?

51. What’s the craziest date you’ve ever been on?

52. If the world was ending tomorrow, what would you want to do today?

53. What do you consider to be your greatest skill?

54. What would you try if you knew you couldn’t fail?

55. What’s your dream vacation? How would you get there?

56. What’s on your bucket list?

57. Who would you want to be trapped in an escape room with?

58. Describe your life up to this moment in five words.

59. What’s the craziest dream you’ve ever had?

60. Do you like baking or cooking better?

61. Would you rather learn self-defense or gymnastics?

62. If you could learn any language, what would it be?

63. What was your favorite game to play as a child?

64. On Thanksgiving, what food are you most likely to go for first?

65. What’s the weirdest inside joke you’ve ever had?

66. What’s your preferred clothing style? Do you like to get all dressed up?

67. What’s your favorite candy bar?

68. Do you like to dance? Would you say you’re good at it?

69. What’s your favorite thing about the outdoors?

70. If you had to move to a foreign country, which would you choose?

71. If you could have any superpower, what would it be?

72. Who’s your favorite superhero?

73. What, in your opinion, is the most underrated song?

74. What story cliché do you actually like?

75. What’s an old movie that you think everyone should see?

Flirty Questions to Ask a Guy Over Text

You’ve met. You’ve hit it off. And now, you’re texting each other!

Congratulations for getting this far, but the flirty questions don’t have to wait for face-to-face time. Use the following questions to keep the flirtation going

 76. What three words would you use to describe yourself?

77. What’s your favorite emoji?

78. What’s your biggest pet peeve?

79. What’s your favorite season? Why?

80. Who do you look up to the most?

81. What’s your favorite ice cream flavor?

82. What’s your favorite holiday? How do you like to spend it?

83. What’s your favorite movie to watch with friends or company?

84. What’s your favorite feel-good movie for when you’re feeling down?

85. What’s your favorite holiday movie?

86. What’s your favorite thing to do at a party?

87. Who’s your favorite actor?

88. What’s your favorite song?

89. Where are you sitting and what are you wearing right now?

90. What emojis would you use to describe your day?

91. Will you send me a gif that captures your current mood?

92. Do you have any pets?

93. Do you prefer phone calls or texting?

94. If you could have anything for dinner, what would it be?

95. What does your name mean?

96. Will you send me a screenshot from your favorite show?

97. What’s your favorite social media site?

98. What app do you use the most?

99. Do you like dark chocolate or milk chocolate?

100. What’s your favorite kind of cheese?

101. Who was your first crush and why did you like her?

Subtle Flirty Questions to Ask A Guy 

You'll want to keep the flirtation subtle if you’re sussing this guy out as potential boyfriend material. Anyone could ask the following questions without sounding overly curious or flirty. Using too many of them at once, though, could blow your cover. 

102. What’s the first thing you notice about a person when you meet them?

103. Would you go out of your way to be nice to someone? And if yes, who?

104. What’s the most important thing in your life right now?

105. Where do you think your best qualities came from?

106. Do any words make you deeply uncomfortable? Would you be willing to write them down, so I can avoid saying them? 

107. What is your favorite social media platform, and what do you like about it? 

108. What is your favorite way to spend a cold winter day (or a hot summer day)? 

109. What would you give up if you had to give up one of your kitchen appliances?

110. What would you keep if you could only keep one of your kitchen appliances?

111. What do you like about yourself that you think few people notice? 

112. If you have houseplants, do you give them names? Do you talk to them? 

113. Would you rather take pictures with your phone or a high-quality digital camera? 

114. Are there any foods you never buy that people expect you to have? 

115. Are there any scents or sounds you cannot tolerate? 

116. Who is someone you admire in your field, and what do you admire most about them? 

117.  How do you define success, and how will you know when you attain it?

118. When was the last time you tried something new, and what was it? 

119. What traits do you think a partner would look for in you? 

120. Do you enjoy speaking in front of a group? 

121. Do you have any habits that could drive a person crazy?

122. Are there any personal habits in others that drive you crazy?

123. Ever taken a dare and done something you now regret? 

124. Have you ever watched a movie you didn’t expect to like but ended up loving it?  

125. Would you rather date your high school crush or your celebrity crush?

126. What is your least favorite vegetable? 

Flirty Questions to Ask A Guy to Know Him Deeper 

Ask any of the following questions to get to know this guy on a deeper level. You’re way past the small talk, so don’t be afraid to ask him a question that demands a thoughtful answer. And don’t forget to return the favor if he asks these questions of you. 

127. What’s one thing you’re tired of talking about — or being asked about?

128. What’s your favorite thing to do that doesn’t cost a thing?

129. Have you ever cried during the sad part of a movie? Which one always gets you?

130. Tell me something about you that might surprise me. 

131. If you could choose something to be famous for, what would it be?

132. What have you always imagined doing with a girlfriend that you haven’t done yet?

133. What do you think about before you fall asleep at night?

134. If someone burglarized your home, what’s one thing you would hope they didn’t take?

135. Where do you see yourself in the next five years? And where do I fit in?

136. If you want to college, what did you love most about it? What do you not miss? 

137. What solo activities do you enjoy the most? Or what hobbies do you prefer to do alone?

138. When was the last time you did something big just for you? 

139. What is something you’ve accomplished that you’re really proud of?

140. What is something you’ve been through that has shaped the person you are today?

141. What is something you really want to accomplish this year?

142. If you could replace something in your home for free, what would it be and why?

143. Describe your dream office. 

144. What would convince you to move to a different area? 

145. What do you love about living here? What have you wanted to do here that you haven’t done yet?

146. What does a typical morning for you look like? 

147. What is the most reckless or impulsive thing you’ve ever done? 

148. Do you like surprises? If yes, what’s the best surprise you’ve gotten so far? 

149. What do you think is the point of flirting? 

150. Tell me about something you never want to live without. 

151. What technological advance excites you the most (3D-printed houses, tech implants, etc.)? 

Flirty Questions to Ask A Guy You Just Met 

You’ve just met this guy, and he’s giving off an intriguing vibe. So naturally, you’re curious, hoping to learn more about him. Any of the following questions can serve as ice-breakers. Some are more daring than others. 

152. What are your top five things to do on your weekends or any day you don’t work?

153. What is the bravest thing you’ve ever done (besides talking to me)? 

154. How comfortable are you with people who ask a lot of questions? 

155. How are you with secrets? 

156. What’s your favorite car — and what do you love about it?

157. Have you ever done something crazy to go after something you want?

158. What are your thoughts on vision boards? 

159. Did you work summer jobs as a kid? And if so, what was your favorite?

160. What would you say if you could go back ten years and tell yourself something?

161. If you could change just one thing in the world, what would that be?

162, How do you handle it when you go out, and the restaurant messes up your order?

163. What do you think of the service here so far? How big a tip would you leave them?

164. If you could be a supervillain for a day, what would you be? And what would you do?

165. What is your favorite pick-me-up in the morning? And what helps you wind down?

166. If you had to move at a moment’s notice to take a dream job, would you think, “Challenge accepted!” or “This is how I die”? 

167. What would you do if you took me on a picnic date and it started to rain (a lot)? 

168. Or what’s your idea of a perfect outdoor date (weather permitting)? 

169. Have you ever wanted to climb Mt. Everest? Do you plan to make that happen?

170. If I wanted to go skydiving, would you be game? 

171. Have you ever had a friendly debate with someone that stayed respectful and left you with a better impression of the other person?  

172. What does your perfect day look like? Walk me through it. 

173. What are your thoughts on guinea pigs as pets? Snakes? Exotic birds? Rocks?

174. What do you think is the best place to have a first date, and why? Worst place? 

175. What changes would you make to your neighborhood? For example, would you make it safer for pedestrians and bicyclists? 

176. If you could curate a perfect evening without any limitations, what would it look like? And what role would your date play in it?

177. Imagine you're the author of your own life story. What exciting twist or turn would you write in for your next chapter, and how would a special someone fit into it?

Humorous Flirty Questions

For a fun and playful twist in your conversations, consider introducing some humorous, flirty questions. These can lighten the mood and show off your witty side, making the interaction more enjoyable and memorable.

178. If you were a superhero, what would your flirting superpower be?

179. Would you rather be caught in your underwear at the supermarket or wear a clown wig on a first date?

180. If we were in a movie, do you think you'd be the good cop or the bad cop in our buddy cop dynamic?

181. What's the funniest pick-up line you've ever heard… or used?

182. If animals could talk, which one would be the most flirtatious?

183. Imagine our first date was a game show. What would it be called?

184. If you could only flirt using movie quotes, which one would be your go-to?

185. What's your most embarrassing moment that's actually kind of charming?

186. If flirting were a sport, do you think you'd be an amateur, pro, or the coach?

187. Would you rather have a romantic dinner at a fancy restaurant or a fun night at an amusement park with unlimited rides?

188. What's the silliest reason you've ever had a crush on someone?

189. If you could have any fictional character as your wingman/wingwoman, who would it be?

190. What's the most bizarre talent you find oddly attractive?

191. If our flirting were a battle, would you prefer stealth tactics or a full-frontal charm assault?

192. Would you rather serenade me under my window or write me a love poem in a tweet?

193. If we were both cats, do you think you'd be able to woo me with your meow?

194. What's the most unusual but fun date idea you can think of?

195. If you could invent a new ice cream flavor called “Romantic Gesture,” what would be in it?

196. Have you ever tried to impress someone, and it went hilariously wrong?

197. If we were stranded on a desert island, how would you use your charm to signal for help?

Situational Flirty Questions

For different settings and moments, situational flirty questions can spark intriguing conversations and connections. Tailor your queries to the environment for a more personalized and engaging interaction.

198. At a coffee shop: If you were a coffee, how would you be brewed to perfectly match your personality?

199. During a movie night: Which movie character do you think would make the best partner in crime for an adventure?

200. At a bookstore: If our story was in one of these books, what genre would it be?

201. While cooking together: If we had our own cooking show, what would be our signature dish?

202. On a road trip: If you could pick any place on the map for us to escape to right now, where would it be?

203. At a music festival: Which song do you think could be ‘our song' from the lineup tonight?

204. During a walk in the park: If we were animals in the wild, what duo would we be?

205. At a museum: Which piece of art here do you think could represent our chemistry?

206. At a trivia night: If we were a trivia team, what would our unbeatable category be?

207. While stargazing: Which constellation do you think would be named after us?

208. At a costume party: If we could pull off the ultimate couple's costume, what would it be?

209. During a workout session: If we were workout partners, would you be the motivator or the one needing motivation?

210. At a beach: If we built a sandcastle together, what special feature would it have to symbolize our adventure?

211. At a game night: If we were a team in a board game, which one would we conquer?

212. During a wine tasting: If our relationship were a wine, would it be bold and aged, or light and sweet?

213. At a sports event: If we were both athletes, what sport do you think would best represent our teamwork?

214. On a rainy day: What's your ideal way to spend a rainy day indoors with someone special?

215. During a DIY project: If we had to build something together, what would it be and why?

216. At a holiday party: If we could start a new holiday tradition together, what would you want it to be?

217. On a scenic overlook: If you could pick any place in the world for us to watch the sunset together, where would it be?

Tips for Asking a Guy Flirty Questions

When delving into the art of flirty questioning, it's crucial to strike a balance between curiosity and respect. Here are some tips to guide you:

  • Read the Room: Ensure the atmosphere and his comfort level are conducive to flirty banter.
  • Timing is Key: Pick moments when both of you are relaxed and open to playful conversation.
  • Be Genuine: Let your questions reflect genuine interest rather than just an attempt to flirt.
  • Listen Actively: His responses can offer insights into his personality and interests, guiding your next questions.
  • Respect Boundaries: If a topic seems to make him uncomfortable, gracefully shift the conversation.
  • Use Humor: Light-hearted and witty questions can ease any tension and bring smiles.
  • Personalize Your Approach: Tailor your questions to topics and interests you know he resonates with.

Flirty Questions to Avoid

Flirting should be fun and comfortable for both sides, right? So, when you're thinking of flirty questions, there are a few no-go zones to keep in mind:

Too Much, Too Soon

Jumping into super personal stuff right off the bat? Might want to pump the brakes there.

Assuming Too Much

Questions that make it sound like you're a couple when you're just getting to know each other can be a bit much.

The Negative Nancys

Keep it positive! No one wants to be put on the spot with questions that make them feel judged.

Copy-Paste Flirts

Try to make your questions feel personal, not like you've Googled ‘top flirty questions' and are reading off a list.

Keep it light, respectful, and genuine, and you'll be on the right track.

Final Thoughts

How will you use these flirty questions to ask a guy?

The guy you like will be blown away by your interest in his thoughts and perspective. 

With these flirty questions for him, you can gain a better understanding of the way his brain works while also seeing the way he looks at the world. 

Of course, if he brushes off your questions and keeps dragging the conversation into safer territory (for him), that’s a definite red flag

But if he’s game, and he answers the questions to the best of his ability, there’s no telling what you’ll learn about each other — especially if he asks you to answer them, too.

This list will also give you some ideas for dates, gifts, or any simple gestures.

Make sure to keep this list on hand in case you need a way to deepen your connection.

May you both enjoy learning more about each other.