Overthink This!

Overthink This!

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

  • Episode #54: Cough Your Way Through Feelings or Cry at Every Punchline

    In this episode, things get very socially awkward.

    Would you rather ruin every serious conversation with uncontrollable coughing… or cry every time someone makes a joke?

    From ugly mascara scenarios to choking mid-sandwich, this one spirals fast. Expect chaos, weird coping strategies, and way too much honesty.

    23 min
  • Episode #53: Never Read Again or Endless Laundry Duty

    This episode starts with books and somehow spirals into denim hygiene, hand-washing family laundry, mysterious washing machine products nobody can name, and a shocking number of adults who apparently do not know how often jeans should be washed.

    If you love books, hate chores, or have ever judged someone for not washing their jeans enough, this one is for you.

    20 min
  • Episode #52: Travel and Die a Little or Stay in One Place Forever

    This week’s dilemma: would you rather skip every minute of waiting while traveling and have that time deducted from your life, or never travel to another city or country again?

    We spiral into platforms, airports, red lights, smoking, death, gray hair, and the deeply upsetting realization that most of life is apparently just waiting. Somewhere between adventure and lifespan, we try to choose a side.

    21 min
  • Episode #51: Perfect Relationship With No Spark or Chaos With Great Sex

    This week’s dilemma: would you rather be with someone who matches you in every important way but has zero chemistry, or choose a relationship full of passion and intimacy that is otherwise completely chaotic?

    We spiral into compatibility, attraction, aging, toxic relationships, intimacy, monks, and whether love can survive without physical chemistry. Somewhere between peace and passion, we try to choose a side.

    27 min
  • Episode #50: Relive a Perfect Memory or Delete a Terrible One

    This week’s dilemma: would you rather relive one beautiful memory again, or completely erase the worst moment of your life from your memory?

    We spiral into photo albums, childhood memories, trauma, helplessness, memory distortion, and whether painful moments shape who we become. Somewhere between healing and nostalgia, we try to choose a side.

    30 min
  • Episode #49: Post It Now or Overthink It Into the Grave

    This week’s dilemma: would you rather put an idea out into the world before it feels fully ready, or keep perfecting it until it’s polished, protected, and possibly too late?

    We spiral into overthinking, intellectual ownership, perfectionism, teamwork, creativity, photo albums, and why sometimes “good enough” actually gets things done. Somewhere between protecting the idea and releasing it, we try to choose a side.

    24 min
  • Episode #48: Be Single Forever or Secretly Kiss All Your Best Friend’s Boyfriends

    This week’s dilemma: would you rather stay alone forever and never betray your friend, or secretly kiss every boyfriend your best friend ever has in exchange for your own chance at happiness?

    We spiral from winter books and love triangles into guilt, cheating, friendship, selfishness, and whether honesty actually helps when the damage is already done. Somewhere between loyalty and chaos, we try to choose a side.

    30 min
  • Episode #47: New Year, New Me or Same Chaos, Different Calendar

    This week’s dilemma: would you rather set New Year’s resolutions you’ll probably break, or skip the whole self-improvement ritual and just YOLO your way through the year?

    We spiral into goals, habits, gym routines, reading more, eating less meat, deleting social media, and why vague resolutions fail but tiny specific changes actually work. Somewhere between structure and chaos, we choose our side.

    28 min
  • Episode #46: 10 Songs Forever or a Lifetime of Musical Chaos

    This week’s dilemma: would you rather only hear brand-new songs for the rest of your life, or keep a tiny playlist of favorites and never discover anything new again?

    We spiral into Spotify Wrapped, gym music, Christmas songs, movie soundtracks, singing along to Anastasia, and the emotional chaos of hearing a song that instantly transports you back in time. Somewhere between nostalgia and novelty, we try to choose a side.

    25 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.