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cover art for Episode 27: Bailey Cries.

Disgruntled

Episode 27: Bailey Cries.

Season 1, Ep. 27

Snowed in and slightly losing it, Bailey and Gillian talk winter chaos, cleaning spirals, and why snow days mean very different things depending on who raised you. Between household frustrations, family dynamics, and the general weight of existing right now, the conversation covers societal timelines, personal expectations, and the pressure to have life “figured out” by a certain age.


Somewhere in the middle of all that? Bailey cries. For the first time. After 27 episodes. We don’t make a big deal about it—but it is noted for the record.


From there, things go exactly where you’d expect: modern dating. The hosts break down soft launches, engagement expectations, dating app drama, and one truly unhinged porcelain doll situation. They talk mind games, social media oversharing, and why taking your time in relationships is not a moral failure.


It’s an episode about cleaning too much, caring too much, minding your business, paying the water bill, and remembering that the timeline you choose is, unfortunately for everyone else, the correct one.

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