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Overthink This!

Overthink This!

by Joan Chan & Nela Chereja

Comedy Society & Culture

Episode #65: Honest Conversations about the Pressure to Drink

An honest conversation about not drinking, the pressure to explain yourself, and navigating awkward social situations.

Episode #64: Start Strange or End Sweet

This episode dives into one brutally awkward choice: open with “I had a weird dream about you” or close every convo with “oh btw I love you.” Along the way, we unpack why we’re all a little awkward—and why that’s not always a bad thing.

Episode #63: Dino Danger or Zoo Life

In this episode, we tackle a wild dilemma: would you rather keep a dangerous dinosaur as a pet or live as a monkey in a zoo? Funny, reflective, and a little uncomfortable at times, this one goes further than you’d expect.

Episode #62: Honest Conversations about Work, Life, and Everything In Between

In this episode, we’re trying something different. Instead of unpacking a specific dilemma, we sit down for an open and honest conversation about work-life balance—what it really looks like, how it shifts over time, and the challenges we don’t always talk about. No neat solutions, no clear answers—just a genuine exchange of experiences, reflections, and a reminder that sometimes, talking it through is enough.

Episode #61: Always Know Why or Always Know How To Fix It

Would you rather know the answer to every question except why… or always know why things happen, but never know how to fix them? In this episode, we spiral into one of our most personal dilemmas yet: is it better to understand the reason behind everything, or to just skip the explanation and solve the problem? From broken washing machines and cheating hypotheticals to promotions, purpose, therapy, and the deeply human need to ask “why,” this one got more revealing than expected. One of us discovers she may be happiest as an all-powerful fixer. The other refuses to live without purpose, meaning, and follow-up questions. Naturally, chaos follows.

Episode #60: Lose Written Words or Lose Your Sense of Time

Would you rather lose the ability to understand written words… or stop experiencing time the way everyone else does? In this episode, we start with singing, comfort songs, and dramatic Taylor Swift feelings, then somehow spiral into bathroom signs, audiobooks, circadian rhythm, cave experiments, parenting schedules, and whether time is actually helping us or ruining our lives. One of us would rather live in complete temporal chaos than lose books. The other is surprisingly ready to give up reading and just let technology read everything out loud. Naturally, we overthink all of it.

Episode #59: Wave Back by Mistake or Trip in Front of a Crush

Would you rather accidentally wave at someone who wasn’t waving at you every single day… or slightly trip every time someone attractive walks by? In this episode, we take a very small awkward dilemma and turn it into a full psychological investigation. From missed waves at work and mistaken supermarket smiles to gym-recognition errors, public cringe, tripping in front of attractive people, and the long-term emotional damage of social awkwardness, we overthink every possible angle. Basically: if embarrassment is inevitable, which kind are you choosing?

Episode #58: Perfect Match or Perfect Delusion

What if science could tell you exactly who your perfect match is… but you could never meet them? In this episode, we spiral (as usual) into a dilemma inspired by a DNA-based matchmaking concept: would you rather live your life never knowing your “one true match,” or find out who they are—while being forbidden from ever meeting them? From soulmates and free will to accidental incest (yes, really) and falling in love with AI, we question whether love is something you choose… or something that’s already written in your DNA.

Episode #57: Men’s Thoughts on Loudspeaker or Women-Only Work Life

This episode starts with birthday gifts and “let’s see” travel planning, then spirals into a genuinely chaotic workplace dilemma: would you rather hear the thoughts of every man near you… or work only with women forever? It gets very philosophical, slightly dangerous, and somehow ends with building a mystery women-only company.

Episode #56: Mediocre Forever or Legendary for One Moment

This episode starts with train chaos in Belgium and somehow turns into a full debate about talent, obsession, sports, and whether being legendary is actually worth it if you have to quit immediately after. Would you rather stay mediocre forever and keep playing… or become the absolute best and lose it all at the top? Also: frogs, kickboxing, PhDs, and emotional damage for teachers.

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