
Chace Crawford
Chace Crawford stops by and opens up about frosted tips, heartbreak, and being "okay" at football (this is disputed; we've heard he's quite good). He and Penn reminisce on their Gossip Girl days, whil...
13 Jul 202252min

Evan Rachel Wood
Penn squirms while Evan Rachel Wood reads entries from her tween diary — revealing their mutual crush on each other. Evan delights the gang by recalling the lyrics to Penn’s first love song. Want to...
6 Jul 202246min

Ayo Edebiri
Writer, comedian, actress, and The Bear star Ayo Edebiri charms the crew with stories of first periods and missed Leonardo DiCaprio encounters. Want to submit a middle school story? Go to www.podcru...
29 Jun 202249min

Amy Schumer
Amy Schumer reads an entry from her middle school diary, dishes on her first breakup, and gets real about love and postpartum vulnerability. Want to submit a middle school story? Go to www.podcrush...
22 Jun 202258min

Jenna Ortega
Jenna Ortega gets refreshingly candid about representation, body image, and therapy, and spills the deets on what it was like working with Tim Burton in the upcoming series "Wednesday." Want to subm...
15 Jun 202244min

Rainn Wilson
Rainn Wilson regales the group with stories of heartbreak, courage, and finding your footing when you *really* don't fit in. The cherry on top: he sings! Want to submit a middle school story? Go to ...
8 Jun 202244min

Tati Gabrielle
Sophie and Nava swoon over Penn's YOU Season 3 castmate, Tati Gabrielle, while Penn tries (unsuccessfully) to keep them grounded. Tati opens up about her life, the girls have fun roasting Penn, and th...
1 Jun 202255min

Drew Barrymore
Drew Barrymore joins the crew to share hilarious and heartfelt stories about her turbulent adolescent years in the spotlight. They marvel at the power a little discomfort has in bringing you closer to...
25 Mai 202243min




















