Ready for real talk with zero filters? Shameless Pillowtalk is your go-to podcast where bold meets vulnerable, and no topic is off-limits. From unfiltered musings on life, love, and all the awkward moments in between, host Larry keeps it witty, raw, and relatable. Whether you’re here for the laughs, the life lessons, or just the shameless stories, this is your late-night convo in podcast form. Press play and let’s talk shamelessly!
bad decisions look good on me (feat. @maddzzzystarr)
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.
8 Jun 2026
The Lost Art of Privacy
We live in a world where everything becomes content. Every breakup, every accomplishment, every bad day, every emotional spiral. But somewhere between sharing and oversharing, many of us have forgotten the difference between attention and genuine connection.
This week, Larry dives into the lost art of privacy, why strangers often know more about us than the people closest to us, and how social media has blurred the line between being seen and being known. From emotional validation and oversharing to boundaries, loneliness, trust, and emotional cheating, this conversation gets real about who deserves access to your life—and who doesn't.
Plus, a wild Mailbag Mayhem letter sparks a conversation about emotional infidelity, workplace friendships, and whether "nothing happened" is really the whole story.
If you've ever felt pressured to explain yourself, share every update, or give people access they never earned, this episode is for you.
Because not everything needs an audience to be valuable. Sometimes the most important things in your life are the things you're quietly building when nobody's watching.
1 Jun 2026
Perfection is Bull****
As Mental Health Month comes to a close, Larry shares one of the most personal stories ever told on Shameless Pillowtalk.
After breaking down a few headlines from the week, the conversation turns inward as Larry opens up about his battle with depression, surviving a suicide attempt in 2018, the realities of therapy, and the lessons learned from rebuilding his life. It's an honest conversation about loneliness, healing, asking for help, and the lies our minds can tell us when we're struggling.
Plus, this week's Mailbag Mayhem tackles a listener's relationship dilemma after discovering her boyfriend has been living a secret life online.
Sometimes surviving is enough. This episode is for anyone who's ever felt overwhelmed, exhausted, or like nobody understands what they're carrying.
🎙️ If you or someone you know is struggling, call or text 988 for the Suicide & Crisis Lifeline.
Who has been a guest on Shameless Pillowtalk
Names identified in recent episode analyses. Showing up to five guests.
Joe Mausolf
Queen Neli Sade
@pdmoore_
@shadowminxx74
@rbcclima
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
1 ratings
Podcast Authority Score: 38 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
75
Social presence
0
YouTube
0
Engagement
0
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