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Want to know what’s really going on inside a guy’s head without asking anything too deep too fast? Some solid Would You Rather questions to ask a guy are always a good bet.
To be clear, there’s nothing wrong with going straight for deep questions with a dude (says the person known to ask “when’s the last time you cried?” on a first date). Chit-chat has its purpose, but it’s not exactly the style of probing conversation that’ll help you get to know someone on a real level. So if it’s your instinct to cut straight to the soul-searchy questions, cool! Don’t fight that.
That said, if you’re on the more subtle side, it may feel more natural to build up familiarity with a crush slowly, earning their trust along the way. If that’s you, the best Would You Rather questions to ask a guy can take some of the pressure off by making a game out of asking flirty, funny, and yes, personal questions. It’s low-stakes, high-reward, and can reveal a lot more about a person than you’d think. Like, does he crave adventure or chill nights in? And is he the type to tell all or play it cool? Would You Rather is one way to find out — and we’ve rounded up questions that’ll cover all your bases below, from silly to spicy to surprisingly introspective (without trying too hard).
Make it through the full list? You can always pull more questions over from our roundup of Would You Rather questions for friends. Or, switch to a game of 21 Questions or This or That, and modify some of the prompts to reference where you live, your mutuals, and anything else you’ve got in common. Let the games begin!
In this article, you’ll find:
- Good Would You Rather Questions for a Guy (Low-Key)
- Would You Rather Questions: Spicy & Flirty
- Hilarious Would You Rather Questions for Guys
- Fun Would You Rather Questions for Couples
- Personal Would You Rather Questions to Ask a Guy
Good Would You Rather Questions for a Guy (Low-Key)
- Would you rather stay up all night or wake up at the crack of dawn?
- Would you rather always be 10 minutes early or 10 minutes late?
- Would you rather be known for your music taste or your movie picks?
- Would you rather have a job you love that pays OK or one you don’t love that pays a lot?
- Would you rather share your Spotify Wrapped or your screen time stats?
- Would you rather hang with a big group or keep it to your inner circle?
- Would you rather say a white lie to spare someone’s feelings or share brutal honesty?
- Would you rather be the Samuel or the Darsheen of a travel duo?
- Would you rather get a second chance at one moment or fast-forward through something awkward?
- Would you rather have a night in or night out?
- Would you rather stay in your hometown or move every two years?
- Would you rather share your go-to comfort show or your go-to sad song?
- Would you rather get super into astrology or pretend it doesn’t exist?
- Would you rather be risky or play it safe?
- Would you rather be able to read minds or hear secrets?
- Would you rather have unlimited time or unlimited energy?
- Would you rather answer deep questions or ask them?
- Would you rather travel somewhere new or revisit a favorite spot?
- Would you rather be the “funny one” or the “smart one”?
- Would you rather be able to play any instrument or speak any language?
Would You Rather Questions: Spicy & Flirty
- Would you rather flirt with touch or words?
- Would you rather be chased or do the chasing?
- Would you rather have chemistry that’s electric or comfort that feels like home?
- Would you rather share your fantasies or hear theirs first?
- Would you rather kiss in the back of a movie theater or in the library stacks?
- Would you rather be passionate or be playful?
- Would you rather flirt in public or keep it between just us?
- Would you rather hear what I want or tell me what to do?
- Would you rather risk it and ruin the friendship or stay safe and wonder forever?
- Would you rather be slow and sensual or fast and hot?
- Would you rather play it coy or bold?
- Would you rather have a slow-burn romance or a fall-fast fling?
- Would you rather be the giver or the getter?
- Would you rather make out on the dance floor or in a pool?
- Would you rather feel my breath on your neck or my voice in your ear?
- Would you rather make the first move or wait for me to surprise you?
Hilarious Would You Rather Questions for Guys
- Would you rather accidentally wear matching outfits or have to post a cringe couples caption?
- Would you rather get caught making out by your boss or your parents?
- Would you rather be the guy who does finger guns as a greeting or who yells “let’s goooo” at every sports play?
- Would you rather do an escape room together or build Ikea furniture without instructions?
- Would you rather have your search history leaked or your camera roll?
- Would you rather be the guy who brings a guitar to the party or the guy who won’t stop talking about crypto?
- Would you rather show up to a date overdressed by five levels or clearly in pajamas?
- Would you rather be the guy who requests the Cha Cha Slide at weddings or who claps when the plane lands?
- Would you rather forget your wallet on a date or call the server “mom”?
- Would you rather be the guy who takes gym selfies with captions or the guy who wears a beanie in 90-degree weather “for the vibe”?
- Would you rather accidentally send a flirty text to your family group chat or have to wear Axe body spray every day for a year?
- Would you rather your crush find your old Tumblr or your middle school YouTube channel?
- Would you rather have your ex rate you publicly or your mom write your prompts on Hinge?
Fun Would You Rather Questions for Couples
- Would you rather recreate our first date or do something we’ve never done before?
- Would you rather celebrate lots of little relationship milestones or just one big one every year?
- Would you rather be in a rom-com together or on a reality dating show?
- Would you rather get a truth or a dare if we started playing Truth or Dare next?
- Would you rather go skydiving or scuba diving together?
- Would you rather take a dance class or a cooking class together?
- Would you rather binge-watch a trashy show or go on a digital detox getaway?
- Would you rather surprise each other with small gifts or unexpected plans?
- Would you rather stay at a resort or in the wilderness together?
- Would you rather be locked in IKEA overnight or a theme park after hours?
- Would you rather be snowed in with no Wi-Fi or road-tripping with no AC?
- Would you rather get lost in a new city together or be “regulars” at a favorite local spot?
- Would you rather take turns making decisions or flip a coin every time?
- Would you rather be long-distance for a month or spend 24/7 together for a month?
- Would you rather swap favorite meals or favorite childhood movies for date night?
- Would you rather do karaoke as a duo or be on a competitive trivia team together?
- Would you rather turn our texts into a book or our adventures into a movie?
Personal Would You Rather Questions to Ask a Guy
- Would you rather know what people really think of you or never hear any opinions at all?
- Would you rather change for love or stay yourself, solo?
- Would you rather plan everything or live for the moment?
- Would you rather have more money and less quality time with a partner or less money and more quality time?
- Would you rather do most things with a partner or keep your own routines?
- Would you rather have no kids or minimum four kids?
- Would you rather feel affirmed or feel challenged?
- Would you rather travel back in time to meet your ancestors or forward to meet your descendents?
- Would you rather take center stage or be a supporting cast member?
- Would you rather be known for your ambition or your kindness?
- Would you rather know what happens after death or keep it a mystery?
- Would you rather process things out loud or alone in your head?
- Would you rather be the person friends count on for a good time or for advice?
- Would you rather fall in love once and stay in love forever, or fall in love often and learn from it each time?
- Would you rather be better at expressing yourself or at understanding others?
- Would you rather go back and fix one thing or know how one future decision turns out?
- Would you rather keep the peace or say what you really feel?
- Would you rather someone want you for who you are or who you're becoming?
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