Spill the Spice: 73 Fresh Dirty-ish "Most Likely To" Questions!

By
Boomit Team
May 23, 2025
contents

Alright, the lights are low, the responsible folks are in bed, and it's time to turn up the heat (and maybe the suggestiveness!). These "Who is Most Likely To" questions are strictly for the after-hours crew – the ones who aren't afraid to blush, giggle, and get a little bit risqué. If you're ready to dive into some cheeky revelations about your friends' naughtier sides, you've come to the right place. With 73 prompts to get you talking, remember: what's said in the late night, stays in the late night... mostly! 😉

73 Dirty-ish "Most Likely To" Questions for When the Clock Strikes Midnight:

  1. Who is most likely to have a successful "friends with benefits" arrangement (and actually keep it casual)?
  2. Who is most likely to make the first move in a very direct and unmistakably suggestive way?
  3. Who is most likely to have the highest sex drive in this group, hands down?
  4. Who is most likely to have used a super cheesy pick-up line that, against all odds, actually led to a hookup?
  5. Who is most likely to initiate dirty talk during a steamy session?
  6. Who is most likely to be secretly (or not-so-secretly) kinky and into experimenting?
  7. Who is most likely to own an impressive (and perhaps well-used) collection of sex toys?
  8. Who is most likely to have watched porn in the last 24 hours?
  9. Who is most likely to be surprisingly adventurous and uninhibited in the bedroom, despite a shy public exterior?
  10. Who is most likely to have a hilarious or thrilling story about a public display of affection moment that almost got them in serious trouble?
  11. Who is most likely to have a favorite "position" they always gravitate towards or suggest?
  12. Who is most likely to have a secret (or not-so-secret) stash of sexy lingerie, underwear, or special "bedroom outfits"?
  13. Who is most likely to have a well-thought-out and frequently updated "celebrity free pass" list?
  14. Who is most likely to have created a dedicated "sex playlist" with carefully selected mood-setting music?
  15. Who is most likely to be a surprisingly (or notoriously) loud lover?
  16. Who is most likely to have hooked up with someone significantly older or younger than themselves?
  17. Who is most likely to be genuinely curious about or want to try light BDSM play?
  18. Who is most likely to have an epic "walk of shame" story (or perhaps, a "stride of pride" story)?
  19. Who is most likely to have seriously and frequently fantasized about a threesome?
  20. Who is most likely to actually initiate, organize, or enthusiastically participate in a threesome?
  21. Who is most likely to be exceptionally good at giving massages that always seem to lead to something more?
  22. Who is most likely to experiment with food (whipped cream, chocolate, strawberries, etc.) in the bedroom?
  23. Who is most likely to have a mirror strategically placed in their bedroom (and not just for checking outfits)?
  24. Who is most likely to have a "safe word" – and maybe even a funny or intriguing story about needing to use it (or almost needing it)?
  25. Who is most likely to instigate a late-night skinny dipping session and successfully convince everyone else to join in?
  26. Who is most likely to have a funny, embarrassing, or slightly awkward "sex-related injury" story to tell?
  27. Who is most likely to be very vocal and clear about what they want (and definitely don't want) in bed?
  28. Who is most likely to prioritize cuddling, pillow talk, and aftercare after sex, rather than just rolling over to sleep?
  29. Who is most likely to have a "guilty pleasure" turn-on that they might be a bit shy or embarrassed to admit?
  30. Who is most likely to have a one-night stand story that they still secretly think about fondly (or hilariously)?
  31. Who is most likely to have used handcuffs (fuzzy or otherwise), blindfolds, or other light restraints during sex?
  32. Who is most likely to have made out intensely (and maybe a bit too loudly) in a public (but hopefully dark) movie theater?
  33. Who is most likely to be open to having sex on a first date if the vibe and connection are undeniably right?
  34. Who is most likely to have a "no strings attached" philosophy for some, if not most, of their casual encounters?
  35. Who is most likely to have a very specific (and perhaps unusual or quirky) dealbreaker when it comes to bedroom activities?
  1. Who is most likely to have secretly (or with consent) filmed themselves during a solo session or with a partner?
  2. Who is most likely to have a surprisingly dominant side that fully comes out in the bedroom?
  3. Who is most likely to genuinely enjoy exploring a more submissive or passive role in bed?
  4. Who is most likely to have a mental (or perhaps even written) "sexual bucket list" of things they absolutely want to try?
  5. Who is most likely to have a particular "type" when it comes to a partner's body or specific physical features that really get them going?
  6. Who is most likely to have used dating apps or websites specifically for finding casual hookups or NSA fun?
  7. Who is most likely to have a slightly unusual fetish or kink that they'd only share with their closest, most trusted friends (or a curious partner)?
  8. Who is most likely to get a secret thrill from light exhibitionism or voyeurism (safely, sanely, and consensually, of course)?
  9. Who is most likely to always use "mood lighting," candles, or incense specifically to set the scene for intimacy?
  10. Who is most likely to whisper something incredibly naughty or suggestive at an unexpected but particularly thrilling public moment?
  11. Who is most likely to have a favorite, tried-and-tested "quickie" spot (whether at home or somewhere more adventurous)?
  12. Who is most likely to send a very suggestive selfie or a risqué text to their partner (or a potential new flame) to get things started?
  13. Who is most likely to have "rehearsed" sexy talk, seductive moves, or a striptease in front of a mirror?
  14. Who is most likely to be the one who suggests watching porn together as a couple or with a partner?
  15. Who is most likely to have a wild "sex story" that sounds completely made up and unbelievable but is actually 100% true?
  16. Who is most likely to have a secret "code word" for initiating sex with their regular partner that sounds totally innocent to outsiders?
  17. Who is most likely to have actually joined the "mile high club" or be actively plotting how to do it?
  18. Who is most likely to have a specific outfit (that might not even be lingerie) they wear purely because they know it makes them feel undeniably sexy and confident?
  19. Who is most likely to have "accidentally on purpose" brushed up against someone in a crowded place as a subtle (or not-so-subtle) flirty move?
  20. Who is most likely to be a masterful tease, knowing exactly how to build anticipation to an almost unbearable, yet thrilling, extreme?
  21. Who is most likely to have a "hall pass" agreement with their partner for a very specific, non-celebrity individual or unlikely scenario?
  22. Who is most likely to have a "type" based on someone's profession, uniform, or a particular skill they possess?
  23. Who is most likely to have secretly written (or avidly read and bookmarked) erotic fiction or steamy fanfiction?
  24. Who is most likely to enjoy the thrill of whispering dirty talk or suggestive comments in a public (but still somewhat private) setting, like a quiet bar corner?
  25. Who is most likely to have used a dating app exclusively while on vacation in another city or country, just for the thrill of a holiday romance?
  26. Who is most likely to have a "sex dare" they actually completed and now have a wild, unbelievable story about?
  27. Who is most likely to genuinely prefer energetic morning sex over traditional late-night encounters?
  28. Who is most likely to have a surprisingly naughty or sex-related item on their public Amazon wish list right now (maybe hidden in plain sight)?
  29. Who is most likely to be genuinely interested in trying (or have already secretly tried and enjoyed) tantric sex practices for deeper connection?
  30. Who is most likely to have very strong, vocal, and perhaps TMI opinions on pubic hair preferences (for themselves and their partners)?
  31. Who is most likely to have a "go-to" sexual fantasy or scenario they frequently replay in their mind to get in the mood?
  32. Who is most likely to have kept a "sex trophy" or a small, seemingly innocent memento from a particularly memorable or wild encounter?
  33. Who is most likely to have a signature "seduction scent" (a specific perfume, cologne, or lotion) they wear when they're aiming to impress?
  34. Who is most likely to secretly enjoy the idea of being watched a little bit during intimate moments (by a trusted partner, of course)?
  35. Who is most likely to have mentally (or even physically, in a very private journal) "rated" or ranked their past lovers?
  36. Who is most likely to have a specific, non-obvious song that instantly gets them in the mood for sex whenever they hear it?
  37. Who is most likely to have given (or received and absolutely loved) a full, enthusiastic strip tease?
  38. Who is most likely to have a juicy "sex secret" that absolutely no one in this room knows… yet?

Final Thoughts

Phew! Did things get a little steamy in here, or is it just us? These 73 dirty-ish questions are perfect for those late-night chats when inhibitions are low and the company is close. Whether you learned something shocking, confirmed a few suspicions, or just had a good laugh at your friends' (and your own!) expense, we hope it added some spice to your night.

Now, maybe it's time for a cold shower... or another round of questions? You decide! 😉

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