330 Questions to Ask a Guy

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Questions to Ask a Guy – I have gathered around 340 questions you could ask a guy.

These questions are helpful when you want to know the person or wanted to start a deep connection with them. These will also help you get through conversation without any awkward silent gaps. Because these questions are designed in a way that they will expect more answer then yes/no.

PS: I have aggregated some working tips to get into deep conversation with guys

Tips for Girls to start a healthy Conversation with Guys

If you want a guy to notice you, one of the best ways to do so is to talk to him.

Find a conversation starter

Look for observations or comments you can make to get the conversation started. There are a variety of ways to begin a conversation. Once you’re talking, you can proceed to keep things flowing, allowing you to get to know your crush.

Be yourself

When you really like someone, it can be very tempting to try and be the type of person you think they would be interested in dating. For instance, if the guy is really sporty but you couldn’t care less about sports, you might be tempted to pretend you’re also a big fan. Avoid this. Don’t deny your own interests, hobbies, and friends out of fear of judgement or rejection.

Text him regularly

If you get his number, texting can be a great form of communication that can help you get to know him better. Try to text him once in awhile and see how he responds. This can help you see if he likes you as well. A guy who texts back eagerly is more likely to be interested.

Avoid certain topics

Some topics can tank a conversation, so they should be avoided. If you’re trying to get to know a potential romantic interest, stay away from topics that may make him uncomfortable.

Discuss shared interests

You want to be yourself around your crush, so don’t center all the conversations around him and his interests — let him get to know you, too. Once you’re talking regularly, try to look for shared interests to discuss. This way, you’ll get to know each other better and bond through common traits.Questions to ask a guy 2

Maintain the conversation

During the initial conversation, you don’t want to overdo it. Pay attention to how the guy is reacting. Wrap up the conversation when it seems to have reached its natural end.

Ask questions

Once you start talking, ask some questions. It can be difficult to establish a smooth flow of conversation at first. One helpful tip to remember is that people generally enjoy talking about themselves. If you want your crush to keep talking, ask him questions. This can also help you get to know him better.

Questions to Ask a Guy

  1. What did you want to be when you grew up when you were a little kid?
  2. What is one thing you do now that your younger self would be ashamed of?
  3. Which historical figure would you like to have lunch with?
  4. What is one thing you worried and stressed about that ended up being no big deal?
  5. What is something you wish people would stop talking about already?
  6. What is something you always doubt about yourself?
  7. Which do you prefer: a good book or a good movie?
  8. What is one subject you wish you knew more about?
  9. If you could be fluent in one language, what would it be and why?
  10. What was your favorite toy as a kid?
  11. What was your biggest childhood fear?
  12. What is a random thing that reveals a lot about a person?
  13. What is one book you could read over and over again?
  14. What skill do you wish you could master?
  15. Would you rather have three horrible years followed by the best year of your life or four mediocre years?
  16. What is your biggest irrational fear?
  17. What is something you’re embarrassingly bad at?
  18. What is your most prized possession?
  19. Do you have any feminine qualities?
  20. If you could only eat one food for the rest of your life, what would it be?
  21. What is one thing you never get bored of?
  22. What is your earliest memory?
  23. What is one thing you wish you could remember more clearly?
  24. What topic do you have a lot of useless knowledge in?
  25. Is social media bringing us closer together, or making everyone more isolated and alone?
  26. When was the last time you cried?
  27. What is something that never ends well?
  28. What is one thing you’re judgmental about?
  29. If you had 1 million dollars to donate to a charity of your choice, which would it be and why?
  30. What is something you think should be illegal?
  31. If you had one month to live, what are 5 bucket list items you would do?
  32. What is one thing no one realizes about you?
  33. What are people always surprised to discover about you?
  34. What is your favorite part of the day?
  35. What has been your favorite age so far?
  36. What is something that happened to you that’s so absurd you wouldn’t have believed it if you weren’t there?
  37. If you could go back and re-do one moment in your life, what would it be?
  38. What is your spirit animal?
  39. Do you believe in zodiac signs?
  40. What is one temptation you can never resist?
  41. What is the absolute worst quality a person can have?
  42. Is there anything you’re superstitious about?
  43. Do you think it’s important to keep up with the news?
  44. What is one story you tell that always makes people laugh?
  45. Do you believe in past lives?
  46. What is something that happened in your life that felt like the worst thing at the time, but was really the best thing in the long run?
  47. What is one thing no one will ever know for sure?
  48. What song always takes you back to your teenage years?
  49. When is the last time you laughed so much it hurt?
  50. What is one thing you can never get enough of?
  51. What is one thing that always cheers you up?
  52. What should a healthy relationship provide for the people in it?
  53. If you could only listen to one song for the rest of your life, what would it be?
  54. If you could re-live one year of your life, which would it be and why?
  55. If you could write a note to your younger self, what would you say in three words?
  56. What is one thing that never ends well?
  57. What is one thing you wish you knew as a child?
  58. Which former president would you want to have drinks with?
  59. What would you do differently if you could relive the last three years of your life?
  60. What is an opportunity that came your way that you regret not taking?
  61. What is something that makes you feel like a kid again?
  62. The house is on fire, which three things do you grab?Questions to ask a guy 3
  63. Have you ever dreamed of being famous?
  64. What is one thing standing in the way of you achieving a goal?
  65. What is your favorite memory?
  66. Who is one person you admire the most?
  67. Did you have a happy childhood?
  68. How would you describe yourself in five words?
  69. What helps you stay positive when everything seems to be going wrong?
  70. What is the best and worst part about being a guy?
  71. What’s your biggest guilty pleasure?
  72. When was the last time you used YOLO as an excuse to do something?
  73. If you had three wishes, what would they be?
  74. Have you ever had your heart broken?
  75. Have you ever broken someone’s heart?
  76. What would your dream job be?
  77. What are you insecure about?
  78. Do you want kids someday?
  79. Do you believe in the paranormal?
  80. What’s your favorite ice cream flavor?
  81. What is your least favorite ice cream flavor?
  82. Do you believe in any conspiracies?
  83. Is all this technology making us smarter or dumber?
  84. How do you deal with people you really dislike?
  85. Do you think some people really have psychic abilities?
  86. What absolutely terrified you as a kid?
  87. What is the scariest movie you have ever seen?
  88. What is the funniest movie you have ever seen?
  89. What is the worst movie you’ve ever seen?
  90. If you could change anything about yourself, what would it be?
  91. Have you ever broken the law?
  92. What is one thing you can’t live without?
  93. Do you enjoy small talk with strangers?
  94. Why do you think the divorce rate is so high these days?
  95. Have you ever been addicted to something?
  96. Are you usually ten minutes late, or ten minutes early?
  97. What is the best prank you’ve ever pulled?
  98. Do you like schedules, or going with the flow?
  99. Do you think it’s better to be honest or kind?
  100. Do you have a mantra you live by?
  101. Do you believe love conquers all?
  102. What is your favorite time of year?
  103. Do you have any recurring dreams? What are they?
  104. Is there anything you wish you could change about your family?
  105. What food grosses you out?
  106. Do you have any phobias?
  107. What do you refuse to spend money on?
  108. What is something you’re terrible at that you wish you were good at?
  109. What movie always makes you cry?
  110. When was the last time you got really angry?
  111. What is something that really annoys you when other people do it even though you also do it?
  112. Has there been someone who completely changed your life?
  113. What movie do you quote the most often?Questions to ask a guy 4
  114. What is something that most people don’t appreciate even though they should?
  115. If you could be the best in the world at something, what would it be?
  116. What is something you’ve been wanting to do for a long time but never seem to get around to doing?
  117. What qualities make someone a genuinely decent human being?
  118. What is one topic that always sparks a heated debate between your family?
  119. What was the worst part of high school?
  120. Do you believe in karma?
  121. Is it better to be liked or respected?
  122. What do you consider to be the greatest TV show of all time?
  123. What do you dislike most about dating?
  124. What is the first thing you notice about a woman?
  125. Who was your first crush?
  126. What is your favorite family memory?
  127. What is your favorite family tradition?
  128. Are you happy with your job? What is your dream job? If you work you dream job, what would you change?
  129. Tell me about your friends? What do you value the most in a friendship?
  130. What do you value in a movie?
  131. What’s your favorite way of traveling a foreign country? Camping? Expensive hotels?
  132. If your life was a movie, who would have the lead role and why?
  133. What kind of an experience do you have with pets?
  134. Do you have an older brother or sister?
  135. What was your first drunken experience?
  136. What was your first trip abroad? Did you like it?
  137. Did you take up any sport when you were a kid?
  138. What skill would you say is your best trait?
  139. What thing about your childhood do you miss the most?
  140. What were you afraid of as a child?
  141. What’s your favorite flag and why?
  142. What’s your ideal name for a child? What’s your least favorite?
  143. What is your stance on social media? How long could you live without it?
  144. What are your main criteria when picking a phone? Brand, specs, looks, recommendations from friends?
  145. Did you ever have a paranormal encounter? Are you sure about whether they’re real or not?
  146. What celebrity would you like to meet and why? Do they deserve admiration?
  147. Do you think that people that star in a reality show have self-respect?
  148. How would you describe karma?
  149. Without concrete evidence, how can you dispute the existence of a higher force?
  150. Okay, this question will make or break this – cats or dogs?
  151. How do you think the world will look in 30 years?
  152. Will there ever be a WWIII?
  153. How do you feel about police brutality?
  154. If there is one meal you could eat for the rest of your life, what would it be?
  155. What meal wouldn’t you eat even for a million dollars?
  156. If you won $10 million on the lottery, what would you do with it?
  157. If you could live in one period of history, which period would it be?
  158. What world leader would you sit down and have tea with?
  159. Which ghost would be the funniest to hang out with?
  160. Did you try a cuisine from every continent?
  161. What’s the most insane thing you’ve ever done?
  162. How open to skinny dipping are you?
  163. When it comes to the female body, which kind of look do you appreciate?
  164. I’m sorry for looking at you hard, it’s not that you’re gorgeous or anything. Can you forgive me?
  165. Do you think you can maintain eye contact longer than me?
  166. Did you get your shirt custom-fitted or was it dumb luck that it looks so good on you?
  167. Do you think that this light does us justice?
  168. How would you feel if we moved our location to somewhere more intimate?
  169. How do you feel about a nutritious breakfast after a long night?
  170. This place is too public, wouldn’t you say?
  171. Tell me a fantasy that makes you tremble every time you think about it…
  172. Is it true that the lips of a stranger have the taste of excitement?
  173. Want to go on a cocktail binge and see where we end up?
  174. Let’s put those ears to work… Here’s a fantasy of mine…
  175. What’s the sexiest movie you’ve ever watched? Wanna watch it yet again?
  176. What’s the most sensitive place on your body?
  177. What place on my body do you think is the most sensitive?
  178. It’s high time you put those sexy forearms to use?
  179. Do you have a map? Because I think I got lost inside of your eyes.
  180. I’ve been researching striptease a bit… Want to see how proficient I am?
  181. Did you ever try bondage? To me, it sounds interesting/scary.
  182. Damn, who turned up the AC? It’s hot in here.
  183. What are your feelings about roleplay? What’s your biggest fantasy?
  184. It’s cold, we could use a blanket….
  185. What is a sexual experience that you would like to forget?
  186. What is a sexual experience that you could never forget?
  187. How was your first time?
  188. What areas of making love do you think you can improve at?
  189. Did you ever burst out of laughter during sex?
  190. Casual or passionate?
  191. Rough or gentle?
  192. What is the craziest idea that ever got born inside of your mind?
  193. Are you more active or passive?
  194. What is your stance on capital punishment?
  195. Is global warming real? Storms have been going on for ages, is it possible that global warming is just a cycle of Mother Earth?
  196. Can money buy happiness? What about the fact that happiness while working can lead to more money?
  197. Are drugs necessarily bad or is it just the people who tend to use them?
  198. When do you think euthanasia will be legal? Are you for it or against it?
  199. What is your stance on abortion? Do men have an equal say when it comes to keeping the child or not?
  200. Is work a goal in itself or should it be just a means to achieve the ideal life?
  201. Should technology be considered good or bad for us?
  202. What’s your secret when it comes to coping with stress?
  203. How do you think the pyramids were built?
  204. Do you think communism will work?
  205. Would you sacrifice your life for a loved one?
  206. Do you think reincarnation is possible?
  207. Is what cases is crime ethical?
  208. Should drugs be legal? If yes, under what conditions? If no, why?
  209. Do animals deserve the same rights we have?
  210. If you could throw up on one person, who would it be?
  211. What would you do if you caught a lion sleeping in your back seat?Questions to ask a guy 5
  212. Do you think a bear can juggle?
  213. What was the funniest joke you’ve ever heard?
  214. Do you condone dad jokes?
  215. How far do you think black humor should go?
  216. The only way to resist you is through 3 restraining orders…
  217. Did you know that eating pizza every day is healthier than dying?
  218. What is the stupidest way to die?
  219. If you were born again as Hitler what would you do?
  220. Do you think cockroaches have souls?
  221. Did you ever get drunk in a foreign country and got lost?
  222. What are the disadvantages of shopping online?
  223. What’s the last song you listened on Spotify/iTunes?
  224. What do you think about male-female friendships?
  225. Do you have a favorite documentary?
  226. What good things did Hitler do?
  227. Bananas or apples?
  228. Do you like crosswords?
  229. What word do you hate the sound of?
  230. What word sounds sexy to you?
  231. Dostoyevski or Tolstoy?
  232. One Direction or Justin Bieber?
  233. Florida or New York?
  234. Do you believe in a higher power?
  235. Long-term relationships or causal flings?
  236. Did you want to have kids when you were a kid yourself? How about now? How many?
  237. Are both parents equal in a marriage? Should both be the breadwinner or should the duties be split?
  238. Would you like to be a stay-at-home dad?
  239. Is your career something you would want to do forever or is it something temporary?
  240. Is marriage an important institution or just a piece of paper?
  241. What thing do you want to avoid when being a parent?
  242. What character trait do you resent the most in people?
  243. What character trait do you love the most in people?
  244. Could you be a single parent?
  245. Did you ever suspect you were gay?
  246. What thing do you regret the most in life?
  247. Do you think gay people should adopt?
  248. What’s the worst place you’ve ever vomited in?
  249. When was the last time you peed your pants?
  250. If technology advances, would you try and give birth, if that became possible?
  251. What was the funniest thing to ever happen to you during sex?
  252. What would your mom say about you right now?
  253. What’s the funniest thing you ever did while drunk?
  254. Did you ever fall asleep during sex?
  255. What was the worst situation you ever laughed in?
  256. What is the stupidest situation you almost got killed in?
  257. How much do you think you could hold on without peeing?
  258. What is your most embarrassing dream?
  259. Did you ever get so drunk that you shat your pants?
  260. Do you have any embarrassing pictures of yourself?
  261. What was the worst situation you were ever naked in?
  262. Did you ever got caught skipping classes?
  263. What is your funniest fear?
  264. What was your worst Freudian Lapse?
  265. What’s the scariest thing you’ve ever done?
  266. What is one memory you have from childhood?
  267. What’s the best thing about your life right now?
  268. What is one thing that you’re thankful for?
  269. What’s one thing that you fear?
  270. What’s a favorite memory with a pet/animal?
  271. Who are you closest to in your family?
  272. What’s your family like?
  273. What’s your favorite flavor of ice cream?
  274. What’s your favorite joke?
  275. What’s the stupidest thing you’ve ever done?
  276. If you could rewrite your past, what’s one thing you’d change?
  277. What do you think your best physical feature is?
  278. What’s one thing about yourself, personality-wise, that you like?
  279. When you’re feeling down, who or what is your biggest go-to person or activity?
  280. If you could only eat one food for the rest of your life, what would it be?
  281. What’s one thing you’re super passionate about?
  282. If you had to lose one of your five senses, which would you give up and why?
  283. What’s the hardest thing, physically, you’ve ever done?
  284. What’s the hardest thing, mentally, you’ve ever done or been through?
  285. What’s your favorite thing to do on the weekends?
  286. What’s your zodiac sign? And do you think it describes you?
  287. What’s your biggest regret?
  288. What can always put you in a good mood?
  289. What’s your guilty pleasure snack, drink, or junk food?
  290. If you were forced to eat fast food for your every meal, what would be your top two places?
  291. What’s one thing you wish you could change about yourself?
  292. If you had the option to hit restart and begin life all over again, would you?
  293. Have you ever lost someone close to you? What were they like?
  294. What’s your favorite social media profile?Questions to ask a guy 1
  295. What’s one thing that totally relaxes you when you’re stressed?
  296. What’s a random hobby you’ve always wanted to try but never have?
  297. When was the last time you cried, and why did you?
  298. What scares you the most about the future?
  299. Do you want to have children someday?
  300. What do you imagine your future family will be like?
  301. Have you ever done or accomplished something you never thought you could? What was it?
  302. What’s one thing you could never live without?
  303. Who is one person you could never live without?
  304. What’s your favorite vacation place?
  305. Would you rather go out or stay in on a Saturday night?
  306. What’s your favorite quote, line of poetry, or sentence?
  307. What’s your favorite family memory?
  308. What’s one thing that helps you decide you can trust someone?
  309. Have you been in love before?
  310. How would you explain what ‘love’ is?
  311. What fictional character do you identify with the most?
  312. Are you a superstitious type of person? About what?
  313. Where would you rather live – a big house in the suburbs or a tiny apartment in a great location in the city?
  314. If you could have any job in the world, what would it be?
  315. Ever have any trouble with the law or get arrested?
  316. Which do you like more, a great book or a great movie?
  317. When did you have your first kiss and who was it with?
  318. If you were a waiter and a customer was a JERK , would you spit in their food?
  319. What’s your favorite food to eat?
  320. What’s your favorite type of music to listen to?
  321. What’s the one movie you love more than any other movie?
  322. If you could only eat one food for the rest of your life, what would it be?
  323. What’s the funniest thing that’s ever happened to you?
  324. Has anyone ever walked in on you naked?
  325. How do you deal with people in your life that you don’t like?
  326. What’s the funniest thing that happened in your childhood?
  327. Do you like waking up early or staying up late?
  328. What are you most afraid of?
  329. What actor would play you in a movie about your life?
  330. Guess – what am I thinking about right now?
  331. If you had to give me a nickname right now on the spot, what would it be?
  332. Do you think it’s possible that we met in a previous life?
  333. Pick one to live in: beach, city, or country?
  334. How would you describe me to someone who doesn’t know me?
  335. Which describes your personality… naughty or nice?
  336. What’s the sexiest animal in the animal kingdom?

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