104 of the Deepest, Sexiest, and Dirtiest “Would You Rather” Questions Ever

Have you ever been out to dinner with a long-term partner, on a first date, or in bed after a hookup with your latest FWB and found the conversation is, well, DOA? Before you resort to chatting about the weather to fill that deafening silence or find yourself another victim of the dreaded camera roll scroll (no, Brian, I really don’t need to see your dog Bella from second grade), allow us to make a suggestion: a good, old-fashioned game of “would you rather?”

But first, let us just reassure you that no matter what stage your relationship (/situationship) is in, the occasional lull in conversation is to be expected. Those “what do we talk about” moments don’t mean your connection is doomed or anything, trust. In fact, according to relationship therapist Laura Caruso, not only are those moments of silence completely normal, but they can actually create the perfect opportunity to mix things up—like, say, with a little game!

In addition to filling a conversation gap, Caruso says asking each other “would you rather” questions is a great chance for couples to enhance their connection and learn about each other in a new and unique way. So yeah, not only is “would you rather” fun, but it can also lead to in-depth discussions about things like relationship boundaries, sexual bucket lists, and having kids. Win-win, right?

Having a hard time remembering the best questions from this middle school sleepover staple? Don’t worry, we have you covered. Presenting: 100 sexy, silly, deep, and downright random “would you rathers” that will instantly revive any convo.

Sexy “Would You Rather” Questions to Ask Your Partner

Heat things up with the sexiest WYR questions around. Who knows? These might just spark the hottest sex of your life. You won’t know unless you ask!

1. Would you rather go to an erotic sex club or have an ultra-romantic date night in?
2. Would you rather only have car sex or only have shower sex for the rest of your life?
3. Would you rather never be able to have sex with another person ever again (solo is fine) or never be able to orgasm again?
4. Would you rather be dominant or submissive in the bedroom?
5. Would you rather always be on top or always be on the bottom?
6. Would you rather give or receive oral sex?
7. Would you rather use a cock ring or a wand vibrator during sex?
8. Would you rather have a threesome or swap partners with another couple?
9. Would you rather experiment with temperature play or experiment with power dynamics?
10. With you rather have phone sex or sext?
11. Would you rather watch people have sex or be watched?
12. Would you rather use a butt plug or nipple clamps?
13. Would you rather watch your partner masturbate or be watched?
14. Would you rather only be able to watch porn together or never be able to watch porn again?
15. Would you rather be blindfolded or handcuffed?
16. Would you rather go to a sex party of strangers or people you know?
17. Would you rather give up nipple play or give up fingering?
18. Would rather only be able to have sex in one position forever or give up sex for a year?
19. Would you rather only be able to have sex with the lights on or only have sex with them off?

Relationship-Related “Would You Rather” Questions to Ask Your Partner

Learn more about your S.O. or potential partner with these love-related “would you rather” questions. Just remember to keep the lines of communication open if you disagree on a question—this is about talking, not judging.

1. Would you rather commit a serious crime with your partner or turn them in for a serious crime they committed?
2. Would you rather find out after the fact that your S.O. slept with your bestie or with your worst enemy?
3. Would you rather get married after one month of dating or never get married?
4. Would you rather outlive your partner or your partner outlives you?😥
5. Would you rather still be friends with an ex or never talk to them again?
6. Would you rather have seven kids or no kids?
7. Would you rather have a huge wedding or elope?
8. Would you rather run into your most recent ex or both sets of parents on a first date?
9. Would you rather only be able to kiss Spider-Man style (upside down) or The Notebook style (in the rain)?
10. Would you rather marry your most recent ex or stay single forever?
11. Would you rather give up kissing or give up sex?
12. Would you rather never be able to have another date night or never be able to spend another holiday together?
13. Would you rather be stuck in an elevator with your arch-enemy or your ex (lucky you if they’re the same person)?
14. Would you rather have to say “I love you” on a first date or have to wait five years?
15. Would you rather never be able to have kids or never be able to have pets?
16. Would you rather be cheated on or be the one cheating?

Low-Stakes “Would You Rather” Questions to Ask Your Partner

If you need a good warm-up before getting into more serious topics, asking some less-intense “would you rather” questions is a good way to get the creative conversation juices flowing.

1. Would you rather be rich or be famous (not both, sry)?
2. Would you rather give up bread or give up wine?
3. Would you rather only be able to talk on the phone or only be able to text?
4. Would you rather always be 30 minutes early or 30 minutes late?
5. Would you rather know how you’re going to die or know when you’re going to die (month and year, not day)?
6. Would you rather have your browsing history or your texts published?
7. Would you rather be really funny or really smart?
8. Would you rather be more outgoing or more introspective?
9. Would you rather be able to talk to your pet for one hour (they respond and everything) and lose a year of your life, or just go about your not-talking-to-your-pet-life as usual
10. Would you rather only be able to listen to music or podcasts?
11. Would you rather there only be one season all year (think fall all year round) or all four seasons in one week?
12. Would you rather never be able to read another book or never be able to watch another movie?
13. Would you rather time travel 10 years in the future or 10 years in the past?
14. Would you rather never have your favorite food again or never have your favorite drink again (yes, Diet Coke is included)?
15. Would you rather only be able to bike everywhere or only be able to scooter?

Deep “Would You Rather” Questions to Ask Your Partner

Once you’re in the WYR groove, it’s time to get a lil more serious. The below can be thought-provoking and emotional, so either pick out a few of your favorites or ask them sporadically between questions in other categories. This will help you avoid a date where you’re both sobbing hysterically on the couch (unless that’s what you want).

1. Would you rather marry the person of your dreams or have the career of your dreams?
2. Would you rather be able to see the future or read minds?
3. Would you rather be remembered in history for doing something terrible, or be completely forgotten after you die?
4. Would you rather fulfill your greatest wish or resolve your biggest regret?
5. Would you rather lose all the money you earned this year or lose all the memories you made this year?
6. Would you rather trust everyone or trust no one?
7. Would you rather do too much and feel burned out, or have tons of free time but get major FOMO?
8. Would you rather go through life unable to forget anything or go through life unable to remember anything?
9. Would you rather give up all technology (phones, computers, etc.) or give up all art (music, books, etc.)?
10. Would you rather have never met your best friend or never have had your first love?
11. Would you rather never be able to make another memory from this point on or be able to make memories but forget the ones you have now?
12. Would you rather be successful or rather be well liked?
13. Would you rather give up all your childhood memories or all your teenage memories?
14. Would you rather never feel anger again or never feel sadness?

Gross “Would You Rather” Questions to Ask Your Partner

“Would you rather” questions that are so gross you would literally rather do anything else than the options you’re being given are pretty much the bread and butter of this game. Think of it as, like, mental Fear Factor. While they might seem outlandish, these Qs will likely reveal fears, desires, pet peeves, and quirks you otherwise wouldn’t learn.

1. Would you rather it rain slugs or snow mayo?
2. Would you rather wear someone else’s dirty undies or use their toothbrush?
3. Would you rather shower in syrup or expired milk?
4. Would you rather have diarrhea during your wedding ceremony or on your wedding night?
5. Would you rather cry pebbles (ouch) or sweat vinegar (ew)?
6. Would you rather throw up anytime you pet an animal or fart anytime you hear music?
7. Would you rather have really bad breath or really bad B.O.?
8. Would you rather have to eat your own nail clippings or eat a stranger’s leftovers?
9. Would you rather have to wear the same pair of underwear for the rest of your life or never be able to wear underwear again?
10. Would you rather run through a field of cow manure barefoot or get a gallon of bird poop poured on you?
11. Would you rather be constantly sweating or constantly crying?
12. Would you rather drink public toilet water or your partner’s sweat?
13. Would you rather never be able to pick your nose again or never be able to clean your ears?

Holiday “Would You Rather” Questions to Ask Your Partner

Whether you’re sitting around the fireplace in December or by a campfire in July, having a few holiday-related WYR questions ready is an easy way to uncover some interesting facts about your S.O. (or break the ice with new friend/family groups).

1. Would you rather spend every holiday with your (future) in-laws (but not your significant other) or spend every holiday alone?
2. Would you rather make 1,000 homemade Christmas cookies or decorate 50 Christmas trees?
3. Would you rather wear a turkey on your head (à la Monica Geller in Friends) or get pantsed in front of all your friends (also à la Monica Geller in Friends)?
4. Would you rather be notoriously naughty or famously nice?
5. Would you rather kiss one stranger under the mistletoe or let 20 strangers sit on your lap?
6. Would you rather run naked through your office holiday party or through your significant other’s extended family holiday party?
7. Would you rather only be able to have sex to “Party in the USA” or “Born in the USA” for the rest of your life?
8. Would you rather have to carve a pumpkin every day or go caroling once a week?
9. Would you rather only be able to listen to holiday music or never listen to music again?
10. Would you rather have to spend every holiday with your ex or with your ex- best friend?
11. Would you rather only be able to eat holiday foods for every meal or never have a holiday dessert again?
12. Would you rather only be able to celebrate your favorite holiday or be able to celebrate all the holidays but your favorite?

Silly “Would You Rather” Questions to Ask Your Partner

After going deep, it’s time to lighten up the mood with some far-fetched, totally random “would you rather” questions. Some of these are cringy, some are goofy, and all of them are fun to discuss because they’re, frankly, so damn bizarre.

1. Would you rather be itchy or sticky for the rest of your life?
2. Would you rather be able to speak and understand every existing language or know how to talk to animals?
3. Would you rather give up cheese or give up receiving oral sex forever?
4. Would you rather have legs as long as your fingers or fingers as long as your legs?
5. Would you rather accidentally send a nude to your parents or accidentally *gag* receive a nude from your parents?
6. Would you rather never get tired or never have to go to the bathroom ever again?
7. Would you rather be able to fly but not walk or be able to read minds but not talk?
8. Would you rather never be able to pet a dog again or never be able to have an orgasm again?
9. Would you rather win The Circle on Netflix and gain 50,000 followers or get left at the altar like on Love is Blind on Netflix, but gain 500,000 followers?
10. Would you rather go a year with no eyelashes or a year with no eyebrows?
11. Would you rather have to change your name every day or change your hair color?
12. Would you rather have scales or fur?
13. Would you rather have to share a closet with Steve Jobs or Elton John?
14. Would you rather always forget your keys or never be able to remember another song title?
15. Would you rather be a Barbie or a Bratz doll?