People Pleasers

People Pleasers

Welcome to People Pleasers! Join Leah Rudick and Jessica Michelle Singleton each week as they laugh at themselves and the world around them. They’re on a neverending quest to care less what people think while still desperately needing everyone to like them. They get into everything from woo-woo self-improvement to blatant self-sabotage, and all the totally normal and definitely not weird (RIGHT??) ways they move through the world. Pour a drink and come gab with your best worst millennial girlfriends. Or don’t! No worries if not!

Episodes

October 27, 2026 • 48 mins

Jessica and Leah unpack the paralyzing stress of wedding planning and the hilarious agony of trying to please everyone. The duo dives into condescending Beverly Hills catering gigs, NASCAR-themed wedding fantasies, Dollywood bachelorette throwbacks, and the chaotic glory of 90s mall food courts and baked potatoes. Got a people-pleasing disaster or a conversation you're too terrified to have? Email pplpleaserspod@gmail.com and remem...

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Leah and Jessica celebrate Leah’s birthday by exposing their deepest insecurities, weirdest habits, and desperate need for gold stars. The duo breaks down Sweet Lady Jane birthday cake trauma, kindergarten-style adult star charts, getting kicked out of Erewhon, and the lawless golden era of 90s buffets. Got a people-pleasing disaster or a crazy lie? Email pplpleaserspod@gmail.com and remember to rate, review, and subscribe!

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Leah and Jessica dive headfirst into fall by taking a look at their worst habits. The duo breaks down autumnal cravings, strict birthday rules, childhood liquid soap punishments, and some deeply questionable female biology theories. Got a people-pleasing disaster or a crazy lie? Email pplpleaserspod@gmail.com and remember to rate, review, and subscribe!

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Mark as Played

In the debut episode of People Pleasers, comedians Leah Rudick and Jessica Michelle Singleton have a hilarious, off-the-rails chat about trying—and mostly failing—to stop pleasing everyone else. From picking fights with driverless Waymos and surviving disastrous teenage driving lessons to high school freestyle rap battles and theater trauma, the duo leaves no awkward memory unexamined. Got a people-pleasing nightmare st...

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Mark as Played
October 5, 2026 • 43 secs

Welcome to People Pleasers! Join Leah Rudick and Jessica Michelle Singleton each week as they laugh at themselves and the world around them. They’re on a neverending quest to care less what people think while still desperately needing everyone to like them. They get into everything from woo-woo self-improvement to blatant self-sabotage, and all the totally normal and definitely not weird (RIGHT??) ways they move through the w...

Listen
Watch
Mark as Played

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