4x 21 Sweet & Naughty Questions to Ask a Guy and Entice Him

Want to get to know your crush a little bit better? Here are four sets of 21 questions to ask a guy in all different categories.

21 questions to ask a guy

Questions are a fun way to get to know a guy, especially if he isn’t much of a natural chatterbox. In fact, questions are pretty much the best resource you have whether you’re going out on your first date, or you’re strapped for conversation on your fiftieth!

There are plenty of different kinds of men out there, all willing and unwilling to share different aspects of their life with you. For this reason, we’ve delved into four different categories of 21 questions to ask a guy: would you rather, entertainment questions, family/relationships, and, of course, the one we’re all interested in – sex!

Put on your quiz-show hat and let’s get asking. From nerdy to fun and sweet to sexy, here are questions you can ask a guy.

21 would-you-rather questions to ask a guy

Want to break the ice with your guy? Why not start with would-you-rather? This awesomely ridiculous game pits one idea against another, forcing your crush to choose his outcome. Whether your questions are serious or silly, we swear you’ll both have fun with this one.

#1 Would you rather be able to swim really well or run really fast?

#2 Would you rather be a dog or a cat?

#3 Would you rather live without chocolate or orgasms?

#4 Would you rather ride a whale or ride an eagle?

#5 Would you rather be rich and unhappy or poor and in love? [Read: 30 would-you-rather questions that’ll leave anyone thinking]

#6 Would you rather be a contestant on Wheel of Fortune or Jeopardy?

#7 Would you rather live in the Marvel or DC universe?

#8 Would you rather drink tea or coffee?

#9 Would you rather live without your cell phone or your iPod?

#10 Would you rather be a daddy to a fur baby or a real baby?

#11 Would you rather forget who you were or forget everyone else in your life?

#12 Would you rather drink Coke or Pepsi?

#13 Would you rather never be able to orgasm, or never be able to make your partner orgasm?

#14 Would you rather be deaf or blind?

#15 Would you rather guest star in an episode of the Simpsons or South Park?

#16 Would you rather be able to meow and live nine lives or talk and only live one?

#17 Would you rather have no fingers or no ears?

#18 Would you rather control time or control the elements?

#19 Would you rather have no testicles or have testicles the size of grapefruits?

#20 Would you rather have stretchable arms or stretchable legs?

#21 Would you rather chop off your own arm, or chop off a stranger’s arm *but they’ll come back for revenge in 30 years*?

[Read: 30 sexy, dirty would-you-rather questions to ask a guy]

21 family/relationship questions to ask your crush

Getting to know your crush means getting to know the people and circumstances that have shaped his life thus far: his family and past relationships. Take a *sometimes bumpy* journey into the past and get to know exactly what makes your crush tick with these family and relationship questions.

#1 What’s your first memory?

#2 Are you closer to your mom or your dad?

#3 Do you have any siblings?

#4 If yes, which one are you closest to, and least close to, and why?

#5 Were you a bratty kid?

#6 What’s the biggest adventure you’ve ever been on?

#7 Who were your best friends growing up?

#8 Did you ever take a wild animal for a pet home?

#9 Did you ever steal anything as a child?

#10 What was your favorite meal growing up?

#11 What was your first job?

#12 Who was your first kiss? [Read: 60 get-to-know you questions for a new romance]

#13 Did you ever go to a school dance?

#14 How long was your longest relationship?

#15 How long was your shortest one?

#16 Did you ever cheat on any of your high school girlfriends?

#17 Have you ever lived with somebody?

#18 What’s your biggest relationship pet-peeve?

#19 What’s your absolute relationship deal breaker?

#20 What was your first breakup over?

#21 Have you ever been in love? [Read: 50 easy questions to test your relationship compatibility instantly]

21 questions to ask a guy about entertainment

Guys love entertainment: video games, movies, action, cars – so why not ask him about it? Even if you’re not overly interested in the subject, his insight on the matter may just change your mind about what you’d like to watch or play in the future!

#1 What’s your favorite movie?

#2 Whose better, Clooney, De Niro, or Robert Downey Jr.?

#3 If you could have any superpower, what would it be?

#4 Batman or Superman, who would win?

#5 Do you read comics?

#6 Xbox, PlayStation, or Nintendo?

#7 What’s the longest you’ve ever binge-watched a show for? [Read: The LovePanky dating code for girls you HAVE to know]

#8 What’s your guilty-pleasure TV show/movie?

#9 Who was your first TV crush?

#10 What’s your favorite video game?

#11 Did you ever watch terrible 90s sitcoms?

#12 What’s your favorite show?

#13 What’s the most hours you’ve ever put into a video game?

#14 Who is the most overrated main-star of any show, movie, or game, and why?

#15 Have you ever cried during a video game scene?

#16 Do you still own any action figures from when you were a little kid?

#17 Have you ever played as a female character in a video game? [Read: 15 awkward questions guys wish they could ask girls]

#18 What was the first video game system you ever had?

#19 Have you ever been to a trading card tournament?

#20 What cancelled show should definitely come back?

#21 What was the scariest movie you’ve ever watched?

Sexy questions to ask a guy

Sex is a natural part of life *Duh!* which is why we always end up being so curious about it with regards to… well, pretty much anyone! If you’re doing it, we want to know the “who, what, when, and how” of it. If you’re not the jealous type and you love learning about your man’s sexual preferences, get ready for 21 questions to ask a guy about sex.

#1 Do you want your girl to spit or swallow?

#2 What’s your favorite sexual position?

#3 Have you ever had sex in public? [Read: 40 naughty, playful texts to keep things hot and horny]

#4 How old were you the first time you had sex?

#5 When did you get your first hard-on?

#6 What was it like the first time you went down on a girl?

#7 What’s the longest you’ve ever lasted?

#8 What’s the shortest?

#9 What is your ultimate sexual fantasy?

#10 How often do you masturbate?

#11 Do you watch porn? [Read: 36 random, flirty questions for naughty guys and girls]

#12 If so, what kind?

#13 Would you ever cheat on a girl if you knew she’d never find out?

#14 Would you ever have a male-male-female threesome?

#15 What is the sexiest thing about a girl?

#16 Are you a butt guy, boob guy, or leg guy? [Read: 20 sexy questions to ask a guy and seduce him instantly]

#17 Have you ever had anal sex?

#18 What would you do to me right now if I let you?

#19 Have you ever sent a naked picture to a girl?

#20 Have you ever lied about how big you are?

#21 Well… how big are you?

[Read: How to make any guy uncomfortably horny just by sitting next to him]

There are so many avenues of questions you can ask your man to tantalize him, intrigue him, charm him, or just plain ol’ get to know him better! Whether you’ve been with your guy for one week or one year, we dare you to choose any category of 21 questions to ask a guy and see if you don’t learn something new!

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Waverly Smith

Waverly Smith is a freelance writer who has been getting paid for spreading her sarcastic take on love, life, and sex since 2010. She is many things that peo...

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