Best Questions to Ask a Guy

Best Questions to Ask a Guy

People love feeling safe to talk about themselves. Guys, however, tend to be the less talkative of the sexes. This is where hopes to help!

We have come up with a list of questions that we think will not be too intimidating for a guy to answer. The hope is that the men in your life, whether they are your significant other, your friend, or your brother, will appreciate that you want to know more about them; their opinions, their background, their preferences, and even their fears. 

Best Questions to Ask a Guy

Pick and choose your questions carefully from this list. Guys must be asked questions they feel comfortable answering, or they may put up a front or just not want to talk much anymore. Please enjoy this list as it helps you to strengthen your relationships with the guys in your life.

1. What’s your all-time favorite movie?

Even the guys who don’t like to talk much will find this an easy conversation starter.

2. What’s the most random talent you have?

Get a guy showing off, take a stupidly hilarious video, and he’s yours.

3. If you won the lottery, what would be the first thing you’d do?

Buy a sports car? Donate to a charity? Invest or pay off debt? The answer to this question can tell a lot about a person.

4. When you were a kid, what was your dream job?

Dive in the deep end of childhood memories and lost dreams!

5. What celebrity do you want to meet the most?

This includes musicians, models, actors, and filmmakers.

6. Who is your role model?

Get the conversation going with some deep, personal questions.

7. What’s something you’ve never been good at?

Nobody’s perfect.

8. What’s your favorite animal?

This is a classic conversation starter right here.

9. If you could go pro at any sport, what would it be?

People love to talk about themselves, but they may hesitate on this one if they aren’t great at sports, but what is considered a sport nowadays, anyway?

10. What’s the riskiest thing you’ve ever done?

Dares count.

11. Which show could you binge-watch multiple times?

The land of Netflix is a wide and wondrous place.

12. If you could meet one dead celebrity, who would it be?

Would it be a former U.S. president? A legendary musician? Maybe one of those infamous mobsters from the 1920s?

13. Is there something you always lie about on your resume?

I guess this one depends on where you draw the line between exaggeration and dishonesty.

14. What is a 5-year goal you have?

Goals are fundamental, so it’s nice to know what they are working on.

15. Up to this point in your life, what have you done to make the world a better place?

This is a broad question, but one that is ultimately the most important.

16. What’s the best kind of compliment you’d like to receive?

Sometimes, it’s hard to figure out how to express how much you appreciate the guys in your life. Hopefully, questions like this are clarifying.

17. What food would you never eat in a million years?

You’d be surprised at some guys’ lack of adventure when it comes to food.

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

This might take a lot of thought, but you’re likely to get more honest answers than you expect.

19. What were you like as a child?

Get ready to hear some funny stories

20. What is your biggest fear?

No intentional spooking now.

21. Do you have any insecurities? 

Make sure to ask this one at the right moment and with kindness; it takes a lot to open up to someone about this

22. What do you expect from a girlfriend?

This is nice to know their expectations, and you can talk about your expectations so that you can have mutual respect for one another

23. What’s one thing about society that always makes you angry?

A little light conversation about Marxist theory and socialism over brunch never hurt anybody.

24. Do you want to have children in the future?

How many would you both like to have?

25. What was the last thing that made you cry?

For guys, this is a weirdly personal question.

26. What are you attracted to in a love interest?

This question could be taken as a physical attraction or a personality trait.

27. Would you rather vacation on a beach or in a cool city?

Surfin’ waves or surfin’ subways?

28. What’s your dream car?

Every guy enjoys talking about their 1964 Ford Mustang mid-life crisis fantasy.

29. Do you have any expectations for yourself?

This is nice to know cause you can see if it is realistic as we sometimes have unrealistic expectations for ourselves.

30. What’s the worst movie you’ve ever seen?

There is a fifty-fifty chance that they’ll answer the Star Wars prequels.

31. What is something you look forward to every year?

If they say their birthday, they are officially basic and, therefore, unworthy of your attention. Just kidding… kind of.

32. What’s your weirdest habit?

The more you find out about them now, the better equipped you’ll be to handle their weird tendencies later.

33. What superpower do you wish you had?

We’ve all wondered where we would fit into the Marvel Cinematic Universe once or twice.

34. Would you say you’re closer to your mom or your dad?

If you alternate between fun and personal, guys are more likely to feel comfortable answering your questions.

35. What’s your biggest phobia?

We’re all afraid of something.

36. What’s your favorite book?

This is a simple question, but it can spark some good conversation.

37. If you had three wishes, what would they be?

Put yourself in Aladdin’s shoes and get creative.

38. What was your favorite cartoon as a kid?

You can have deep conversations about SpongeBob.

39. Describe your perfect burger.

If you’re in the mood for another type of food, replace hamburger with, for example, taco, pizza, sushi.

40. Do you think you’re a competitive person?

You might want to find this out before you start dating. Chances are, you’re better than them at multiple things.

41. What’s your favorite restaurant?

You get your next date night right here.

42. If you could acquire one new skill, what would it be?

Would you want to become bilingual? Develop your painting skills? Maybe you’ve always wanted to learn guitar?

43. What’s something you think everyone should experience at least once in life?

Next activity: make bucket lists.

44. If you could live anywhere, where would you be?

Book a flight. Take a trip. You only live once.

45. Are you ashamed to admit you enjoy romance movies?

It takes a real man to admit how obsessed they are with The Notebook.

46. What do you look forward to each day?

Are you a breakfast junkie? Looking forward to a lazy afternoon? Or maybe you enjoy being productive in the evenings.

47. What ice cream flavor would you eat every day if you could?

In a perfect world, we’d all be able to eat endless amounts of ice cream.

48. What’s something you know you’re overly-judgmental about?

We all have our vices.

49. What is one unhealthy food or treat that you are never able to say no to?

They say chocolate does have addictive properties.

50. What is your least favorite fashion trend right now?

No matter what any guy tells you, they all care very much about cultivating their personal style.

51. What do you miss most from your childhood?

If they don’t answer with something like Trix yogurt or Zack and Cody reruns, did they really have a childhood?

52. What’s your favorite holiday?

Reminiscing on similar holiday memories together is a great way to bond.

53. If you had the resources and the know-how, what kind of company would you create?

Would you be focused on making revenue, helping people, or providing a high-quality product or service to the public?

54. When you’re upset, what is something you do that always makes you feel better?

As hard as it might be to get them to admit it, guys cry, too.

55. Who’s your favorite fictional villain?

The bad guys are often some of the most interesting characters of all.

56. What’s a piece of advice you would give to your younger self?

Wisdom has no age.

57. Who would you haunt if you were a ghost?

Imagine all the big spooks you could pull on your unassuming victim.

58. What’s something that you think was fun to do once, but you’d probably never do it again?

Some things only need doing once… skydiving, for example.

59. Have you ever had your heart broken?

Make sure you trust whoever it is that you’re asking this question.

60. How would you define a good person?

This is a difficult question, but one that definitely merits discussion.

61. Is it more important to you to live a life full of experiences, spent continually doing active things and pursuing goals, or are you content to live a relatively slow but peaceful existence, riding out life gently?

Your life is your own. Make what you want of it.

62. If you were an Olympic athlete, what sport would you compete in?

This is assuming you have the appropriate skill and all.

63. Would you rather always be overheated or too cold?

Continuous sweat versus never ending goosebumps?

64. Do you believe in love at first sight?

Guys who say they don’t believe in this are really just closet romantics.

65. What is your most potent memory from your childhood?

They say smell is the most closely tied to memory. Hence, our choice of the word ‘potent.’

66. What’s your favorite Vine?

Every boy has their favorite Vine compilation. Don’t let them kid you.

67. Would you rather go to work early and get out early or go to work late and get out late?

Get home in time for an afternoon nap or be able to sleep in?

68. What New Years’ resolution do you always make but never really keep?

Let’s be real; this question applies to all of us.

69. What’s the worst job you’ve ever had?

We’ve all gotta’ work for a living.

70. Would you ever date your boss?

Not that there’s anything wrong with this. It just tends to complicate the workplace.

71. Have you ever broken a bone?

There are probably more than a few funny stories to accompany this one.

72. What does your perfect day look like?

Get to know them by becoming familiar with their likes and dislikes and all the things that make them happy.

73. What was one time you stepped out of your comfort zone?

Was it riding a roller coaster, swimming with sharks, or petting a snake? There are so many things we do that put us in uncomfortable situations.

74. What are your career goals?

Good to know for the future.

75. What do you look for in a friend?

Hopefully, you already have some of these qualities because it’s the best when you are not only love interests to one another but also friends.

76. If you won the lottery and were given 1 million dollars, what would you do with it?

You will be able to learn what their goals are as well as their adventure and altruistic side.

77. What is one of the worst things you have done?

You will need to ask this question after you have known each other for a while.

78. Do you have a place in mind where you would like to live?

Do they like more of the city life or the small-town life?

79. Do you have a place you would absolutely not want to move to?

Sometimes there are places people will not live, and that’s okay.

80. Have you ever been injured from playing a sport?

This will either be a painful story or a funny story.

81. Would you rather have a home-cooked meal or go and eat out?

This also may depend on what restaurant you would visit.

82. Do you have a favorite superhero?

Spiderman? Superman? Iron man? Hulk? Just a fun question to ask.

83. If you couldn’t own the regular pet (dog, cat, bird, fish), what would you like as a pet?

I have heard sloths are great!

84. Would you rather choose rock climbing or an amusement park?

This guy could be adventurous, but there are different levels of adventure.

85. How do you feel about a woman having a job after marriage?

Understanding his feelings toward gender roles is essential if he is your love interest.

86. Have you done anything on your bucket list yet?

Maybe you could get some ideas for your bucket list.

87. What social media websites do you look at the most often, but not always post something?

Knowing his social media presence can help you learn how much time and energy he puts towards outward approval.

88. What’s one of your guilty pleasures?

Whether it’s Broadway musicals, steamy soap operas, or some OG Beyonce every now and then, everyone’s entitled to express their inner fangirl/boy.

89. How do you spend a typical Saturday night?

This is important to know, especially when you’re thinking about dating.

90. What’s one accomplishment you’ve achieved that you’re very proud of?

Talking about professional accomplishments is a great way to get to know each other. Plus, it’s a simple way to find out whether they’re boastful or not.

91. What’s a cause you’re very passionate about?

Find out if you have similar interests and can get behind the same causes.

92. What is your favorite TV show?

It’s a simple question, but one of the most crucial to developing a relationship.

93. Describe your dream vacation.

If you could go anywhere, see and do anything, and eat as much of anything you want, what country would you want to do it in?

94. What’s the cheesiest joke you can think of?

All guys are amateur comedians.

95. When you were a kid, what was your favorite toy?

We all loved our action figures and Legos when we were kids.

96. What kind of animal would you be if you could be any animal?

Don’t fool yourself; we’ve all wondered about it.

97. What’s Thanksgiving dinner like in your family?

Nothing compares to the absolute tomfoolery that ensues at most people’s family gatherings.

98. What would you put on an ice-cream sundae, in order of importance?

And remember, if there’s no cherry on top, it’s basically not even a sundae.

99. What’s one thing you would change about your life if you could?

If you can navigate the conversation from ice cream sundaes to introspective hypotheticals without getting awkward, consider yourself a talented conversationalist.

100. If you had to eat the same dessert with every meal, what would it be?

There are some sweet things you can never grow tired of.

101. Who’s your favorite Marvel superhero?

Avengers, assemble!

102. Would you say you’re a spiritual person?

There’s no right answer to this question. It all depends on how you define ‘spiritual.’

103. What’s the best piece of advice you’ve ever received?

A good piece of advice: ask this to everyone you meet. Collect life advice like it’s gold.

104. What movie do you wish you could have starred in?

You might not be an actor, but you would have memorized Pi if it meant you could have landed this role.

105. What’s your preferred news source?

With all the ‘fake news’ circulating today, it’s important to get your facts straight.

106. Do you think Bigfoot is real?

This is a hilarious conspiracy theory to speculate about… until it isn’t.

107. What fictional lawyer character would you want to represent you if you ever got in trouble with the law?

Most of us have never thought about this before, but it’s an interesting question.

108. Would you rather be smart and ugly or dumb and handsome?

These are very arbitrary terms, so there’s technically no wrong answer.

109. Would you swim with sharks?

More like, would you risk your life just to be able to say you survived it?

110. Would you ever quit your job to live out the rest of your days roughing it in the woods?

Deep down, every man wants to become Ron Swanson.

111. When you were a teenager, what was one thing you did that you thought was cool and unique but that, looking back, you realize everyone was probably doing it?

We all wanted to be hipsters and punk rockstars. You’re not the only one.

112. Have you ever had an idea for a book, movie, or TV series that you think would become popular if it were created?

Think about it; every culture-defining piece of art came from some random, imperfect person somewhere, sometime.

113. What’s something you wish people didn’t know about you?

Okay, so this is kind of difficult to answer. I would not recommend asking on a first date.

114. Have you ever tried to write a book?

The weird ways in which humans attempt to convey the inner-workings of their minds.

115. What type of music do you enjoy listening to?

Okay, so this is a more ‘first-date’ kind of question. Don’t get too caught up, though. Music taste often changes over time.

116. Have you ever experienced deja vu?

Is there anyone who hasn’t?

117. If you were a girl for a day, what would you do?

This kind of question could start all kinds of arguments. Play nice, kids.

118. What’s the weirdest fictional character you had a crush on as a child?

You know as well as I do that they made those Disney princes and princesses unnecessarily attractive.

119. What would your dream mansion look like?

We all have ever-changing preferences, but no one in their right mind would even think about getting rid of the dream mansion hot tub room.

120. What would you do if we were in zero gravity?

It’s like flying, but also not.

121. If you were a vegetable, what vegetable would you be?

This question requires intellect, extreme concentration and self-reflection, and a sound mind.

122. What’s something you believe that most people don’t?

This is an excellent question to ask when you’re trying to separate the fake guys from the genuine guys.

123. What’s something that many people enjoy or participate in, but you could never understand why they enjoy it?

The way they answer this says a lot about who they are and whether or not they conform to society’s norms.

124. What ice cream flavor fits your personality the best?

Comparing your personality traits to food is one of the safest ways to keep a conversation going.

125. Do tall girls make you feel insecure?

Only guys who don’t have a sense of self-worth are put off by tall women.

126. If someone had something stuck in their teeth or on their face, would you tell them?

The number of people who would genuinely feel uncomfortable pointing out the piece of lunch stuck in someone’s teeth is astronomical.

127. Which celebrity do you think would be the most boring person to have lunch with?

Gossiping about celebrities is one of the most harmful of American pastimes.

128. If you owned a boat, what name would you give it?

Remember, every boat is a ‘she.’

129. If you had to lose one body part, what would it be?

Don’t underestimate the importance of the pinkie toe.

130. Do you believe in magic?

There are weirder things to believe in.

131. What’s a compliment that you’ve received that was actually a masked insult?

And they always tend to come from an in-law.

132. If you could change your name, what would you change it to?

This is technically legal, but maybe try not to give yourself any ideas.

133. What’s a famous quote that everyone considers to be the truth, but it’s actually completely untrue?

Sometimes, the poets were just dead wrong. You be the judge.

134. What’s your number one goal in life right now?

It’s nice to know someone’s priorities.

135. If you were going to die in an hour, what would you be doing right now?

It’s kind of a morbid question, but definitely one worth asking.

136. What’s a book that you’ve read that’s significantly impacted your life?

Books are one of the best ways to spread new ideas, and by reading them, you’re able to form your own.

137. Do you prefer routine to spontaneity?

Sometimes, it’s best to find a healthy balance of both.

138. What’s the most challenging or intimidating aspect of your life right now?

Everyone deals with difficulties and complications in their lives.

139. What’s something you’re absolutely sure you’ll never do?

This one might take a bit of thought.

140. What do you think is your worst trait?

We are all our own worst critics.

141. What do you think is your best trait?

Try not to get too cocky.

142. Would you rather go to an art, history, or science museum?

Find out what they’re interested in and get an idea for your next date!

143. What kinds of situations make you feel a sense of complete panic?

Everyone has experienced the feeling of not having control over situations. Sometimes, it’s nice to be able to talk to someone you trust about those feelings.

144. If you could travel to the year when your parents were your age, would you want to know and befriend your mom or dad more?

Some major Back to the Future vibes.

145. What’s something that motivates or inspires you?

Whether it’s Shia Lebouf screaming ‘Just do it’ or Beyonce hypin’ you up, we all have that one thing that always pushes us further.

146. How long did you go thinking Santa Claus and the Easter Bunny were real?

We all had to have our little child-sized hearts broken by this news at some point.

147. What’s your favorite movie scene of all time?

“We’re flying, Jack!”

148. Would you rather be famous as an athlete or as an actor?

For certain movies, actors are athletes.

149. Generally, do you trust homeless people that beg for money on the side of the road?

This is a seemingly random question, but if you’re looking for a new way of thinking, it might be a good talking point.

150. What is a romantic gesture that you’ve seen happen in a movie, that you would be brave enough to attempt in real life?

Would you hold a boombox over your head? Serenade a girl from a balcony? Dash through an airport and even pay for a ticket? What would you do for love?

151. Do you have any nicknames?

There are almost always a few endearing stories behind a nickname.

152. Where do you draw the line between love and obsession? When does it become too much?

They say love drives you crazy, but how much is too much?

153. Is there anyone you would sacrifice your life for?

Yeah, this is more of a third date question… or a fifth.

154. What’s something that keeps you up at night?

For some, the night is when we feel most awake.

155. How do you want to be remembered?

There are a billion different ways to answer this question. Just keep in mind that it’s a pretty heavy topic, so go easy.

156. Do you believe in fate?

As opposed to chance? Destiny? Reality as one giant government simulation???

157. What makes life worth living for you?

When it comes down to it, we are the choices that we make.

158. Do you have a life motto?

After all, we’re just a bunch of little humans, looking for our way to happiness.

159. Do you think you can tell a lot about a person by the way they look on the outside?

People-watching is sometimes a competitive sport.

160. If your house was on fire, what three things would you grab to take with you?

This is a simultaneously anxiety-inducing and thought-provoking question.

161. If you could only watch one movie for the rest of your life, what would it be?

Would you risk growing bored of your all-time favorite, or would you purposely choose a movie that means nothing to you now, one that you can’t possibly grow more tired of than you already are?

162. When you go to the zoo, what’s the first animal you want to see?

Definitely a major decision.

163. What do you think your best physical feature is?

Though we all have self-confidence issues, each of us has one thing that we like about ourselves.

164. If you had to lose one of your five senses, what would you lose?

Imagine what life would be like if you lost all sense of feeling, sight, hearing, taste.

165. What’s the hardest mental test you’ve had to take?

The SATs? Maybe a Bar Exam? Freshman finals?

166. What’s one thing that defines you?

Leave this question intentionally vague.

167. If you had the chance to travel through space with an alien species as their guest and friend, would you?

Are they more of a Scully or a Mulder?

168. If you were forced into self-isolation or quarantine due to the outbreak of a global pandemic, what would you spend your three months off doing?

2020 has been a rough year for us all.

169. Have you ever made a decision that changed your life, and if so, what was it?

We all have to make tough choices at one point or another in life.

170. What’s your favorite type of chips/bagged junk food?

Are you a sucker for Doritos or more of a Cheetos man?

171. If you had the option to hit the restart button and start life all over again, would you do it?

This requires a bit of introspection, and it’s kind of a scary prospect.

172. What kinds of YouTube videos do you most often watch?

The internet is a vast and varied place.

173. Have you ever accomplished something you never thought you’d achieve?

College, for example, seems pretty insurmountable until you’ve finished and realized that you’ve finished.

174. What’s your most-used social media app?

You might want to slip this one in there to lighten the mood between the profound and daunting questions.

175. What scares you most about the future?

Every day brings a plethora of possibilities if you think about it.

176. What’s a random hobby you’ve always wanted to try but never have?

Let’s be real; we all get pretty busy handling everyday life.

177. When was the last time you cried, and what caused it?

For guys, this is often a tough question, but it’s important to be open and genuine when it comes to emotions.

178. What’s a move someone would make that might help you decide whether to trust them?

It’s more than likely that no one has ever thought about this, but it’s worth thinking about.

179. What’s your go-to drink/food/activity when you’re sick in bed?

Campbell’s chicken noodle soup is a verified cure-all.

180. What’s the scariest thing that happened to you as a kid?

Do you remember the feeling of dropping your arm over the side of your bed and pulling it back in sheer terror because you swear on your life that you felt the breath of a giant invisible monster under your bed?

181. In your opinion, what’s the weirdest word in the English language?

This question will probably start a debate.

182. What’s something that you’ve had since childhood that you keep purely for its nostalgic value?

Do you have some old journals/diaries? Maybe a special blankie or stuffed animal?

183. What’s a word or phrase that you say way too often?

Sometimes, we say it so often that we don’t even realize how often we say it.

184. What’s one thing you can always procrastinate on?

But there is such a thing as productive procrastination, right?

185. What food takes a lot of effort and/or time to make but is, in your opinion, always worth it?

To marinate or not to marinate.

186. What would you immediately do differently if you knew society wouldn’t judge you?

Have you ever wondered how much better life would be if we lived free of judgment?

187. When do you feel most like yourself?

Think of something that just brings out the best in you.

188. If you could eliminate all your fear, what would you do first?

Would our lives be fuller or only riskier?

189. What’s your most prominent pet peeve?

People can be pretty annoying sometimes.

190. Do you think blunt honesty is better in a relationship than harmless white lies?

This is probably situational, but some people can’t stand either.

191. If you were put into the Hunger Games, how long do you think you’d survive?

Not that this is super essential or anything, just cool to theorize about.

192. Would you rather have all the riches in the world but no one to share them with or be poor as dirt with a family that loves and supports you no matter what?

Of course, there’s a loophole to this question, but that’s not the point of asking it.

193. What restaurant commercials never fail to make your mouth water?

These advertisers are just getting better and better.

194. When making tough decisions, are you more likely to follow your head or your heart?

This question might take your guy by surprise.

195. Does hanging out with other people wear you out or liven you up?

This is an easier way to ask if they’re more extroverted or introverted.

196. What’s something that makes you feel alive?

A beautiful sunset? Maybe a particular song? Or even a piece of art?

197. As you’ve grown older, what are some of your experiences that have changed your perception of right and wrong?

Ethics play a significant role in relationships, so this is a fundamental question to ask.

198. What’s something you hope to have accomplished by this time next year?

Talking about goals and ambitions is one of the best ways to get to know each other.

199. Are you the kind of person that would rather buy the new iPhone the week it comes out or wait until your current iPhone stops updating before buying the upgrade?

This says a lot about what your guy prioritizes.

200. What would you NOT do for 5 million dollars?

Expect some crazy answers for this one.