EPISODE · Jun 15, 2026 · 2H 2M
bad decisions look good on me (feat. @maddzzzystarr)
from Shameless Pillowtalk · host Larry Cooper
This week on Shameless Pillow Talk, we're embracing the fact that some of our best stories started with a terrible idea.From birthday disasters and spontaneous trips to Houston, to getting confronted over an Instagram unfollow from a year ago, to realizing everybody in San Diego somehow knows everybody. We're unpacking the kind of chaos that only makes sense in hindsight.Joining me this week is Maddie, from Alyse, and what started as a simple conversation quickly turned into an unfiltered deep dive into friendship, dating, nightlife, creativity, boundaries, age-gap surprises, social media drama, and the moments that make you stop and ask, "How did we even get here?"It's messy. It's honest. It's hilarious.And somehow, bad decisions never looked better.Grab a drink, get comfortable, and let's get shameless.
What this episode covers
This week on Shameless Pillow Talk, we're embracing the fact that some of our best stories started with a terrible idea.From birthday disasters and spontaneous trips to Houston, to getting confronted over an Instagram unfollow from a year ago, to realizing everybody in San Diego somehow knows everybody. We're unpacking the kind of chaos that only makes sense in hindsight.Joining me this week is Maddie, from Alyse, and what started as a simple conversation quickly turned into an unfiltered deep dive into friendship, dating, nightlife, creativity, boundaries, age-gap surprises, social media drama, and the moments that make you stop and ask, "How did we even get here?"It's messy. It's honest. It's hilarious.And somehow, bad decisions never looked better.Grab a drink, get comfortable, and let's get shameless.
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bad decisions look good on me (feat. @maddzzzystarr)
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