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!
Billionaire Bunkers, Spray Tan Trauma & Ham the Dog
Hosts Leah and Jessica interview Ham the dog about navigating micro-people-pleasing, from spray tan trauma to billionaire bunker plans.
27 Oct 2026TRANSCRIPT
Fancy Men, Wedding Panic & Baked Potato Nostalgia
Hosts Jessica and Leah explore wedding planning stress and the challenge of pleasing everyone, sharing stories of catering gigs and nostalgic food court memories.
20 Oct 2026TRANSCRIPT
Rich People Cake, Star Charts & Erewhon Scraps
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!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
13 Oct 2026TRANSCRIPT
Pumpkin Muffs, Birthday Demands & The Goo Girls
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!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
6 Oct 2026
Alpha Drivers, Robot Takeovers & High School Drama Club Nightmares
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 story or an outrageous lie of your own? Send it to pplpleaserspod@gmail.com, and don't forget to rate, review, and subscribe!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
5 Oct 2026
Introducing 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!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Inside a recent episode
Billionaire Bunkers, Spray Tan Trauma & Ham the Dog
Published 3 Nov 2026 · Transcript excerpt
[…] The one that I went to back then, it was like you go into a shower and there's not like a person there spray tanning you. No, it's just like – It just sprays you. And it was like the day before homecoming. It was my first time going to a school dance. Oh, no. And it turned me full orange. This color? […]
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