Overthink This!

Overthink This!

By Joan Chan & Nela CherejaComedySociety & Culture
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Overthink This! episodes

  • Episode #15: Subtle Forever or Split Every Bill

    In this episode, the dilemma is surprisingly social: would you rather always speak in subtleties and beat around the bush, or always go Dutch when eating out no matter the people, the occasion, or the bill?

    What starts as a question about money quickly turns into a conversation about fairness, friendship, cultural habits, treating people, hosting at home, and the awkward feeling when generosity stops feeling mutual.

    26 min
  • Episode #14: One Pair of Jeans for Life or Two Flies Above Your Food

    In this episode, the dilemma starts with fashion and somehow turns into food logistics, blended meals, beach outfits, wedding loopholes, and the exact legal definition of “always wearing jeans.”

    Would you rather wear one single pair of jeans for the rest of your life, or always have two flies circling above your food? The discussion spirals into body shape, favorite jeans, Dutch summers, fashion rules, and increasingly creative ways to outsmart both options.

    20 min
  • Episode #13: Delete All Your Photos or Lose Spring Forever

    In this episode, the dilemma sounds simple at first, but quickly turns into a full-on debate about memories, photo albums, Dutch weather, and emotional attachment to pictures.

    Would you rather delete every photo you’ve ever taken, including printed albums, or skip spring forever? The conversation spirals into camera habits, Meta glasses, winter jackets, heating arguments at home, and just how differently people experience cold, memories, and seasons.

    27 min
  • Episode #12: Daily Mystery Tattoos or Permanently Stinky Shoes

    This episode starts with a bizarre dilemma and somehow turns into a very passionate tattoo conversation. Would you rather wake up every day with tattoos showing what you did yesterday, or always wear shoes that noticeably smell like dog poo?

    From there, the conversation goes into tattoo rules, tattoo regrets, tattoo cravings, superstition, meaning, visibility, and why all three somehow choose tattoos without much hesitation.

    24 min
  • Episode #11: No Men for a Year or Heels 24/7

    In this episode, the dilemma starts funny and quickly gets deeper: would you rather only talk to women for a whole year, or wear high heels everywhere, every day?

    What follows is a thoughtful conversation about International Women’s Day, equality, gender roles, beauty standards, how kids are shaped by labels, and the strange ways society decides what counts as “feminine” or “masculine.”

    24 min
  • Episode #10: Doomscroll Forever or A Bladder That Hates You

    This week’s dilemma: would you rather be confronted with negative news all the time, or wake up five times every night to go to the bathroom?

    We spiral into anxiety, doomscrolling, UTIs, climate change, war, media overload, and how much bad news a person can realistically absorb before losing their mind. Somewhere between sleep deprivation and emotional exhaustion, we try to choose a side.

    24 min
  • Episode #9: Perfect Health or Obscene Wealth

    In this episode, the dilemma sounds simple but gets deep fast: would you rather be the healthiest person on earth, with no pain, no wrinkles, and no complaints — or be obscenely rich?

    What starts as a “health vs wealth” debate turns into a candid conversation about beauty standards, cosmetic procedures, insecurity, social media pressure, aging, and whether money actually changes happiness. Plus: a real update on the no-sugar challenge.

    26 min
  • Episode #8: Thorns Every Valentine’s Day or FaceTime Your Parents for Every Kiss

    This Valentine’s-themed episode goes fully off the rails: would you rather sleep in a bed full of roses with thorns every Valentine’s Day, or call your parents on FaceTime every single time you kiss your partner?

    From awkward kisses and spooning habits to bath debates, bedtime chaos, and the exact logistics of sleeping on top of your partner to avoid thorns, this one is romantic, chaotic, and very funny.

    24 min
  • Episode #7: Text No One or Have a Month of Unexpected Breakfasts

    This episode’s dilemma gets chaotic fast: would you rather permanently remove WhatsApp from your phone, or be woken up every day to have breakfast with a too well known personality for a month?

    From morning moods and awkward greetings to first impressions, overthinking social interactions, and whether people actually ask enough questions back, this conversation spirals from one impossible choice into a full personality analysis.

    25 min
  • Episode #6: Sticky Shower Forever or Constant Ugly Crying

    This week’s dilemma: would you rather cry every single time you speak, or always have to shower in a smelly and sticky shower?

    We spiral into hygiene standards, gym showers, bath habits, ugly crying, gesture-based communication, crying at movies, and just how gross a shower has to be before it becomes the worse option.

    23 min

About Overthink This!

From the publisher's feed

A weekly ‘Would You Rather’ podcast where two overthinking friends spiral into chaos, argue lovingly, go wildly off-topic, and still somehow have to choose.