Tom Shows Harland Williams His Chocolate Starfish | 2 Bears, 1 Cave

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This week on 2 Bears 1 Cave, Bert is on a retreat in Istanbul so Tom Segura is joined by the brilliantly bizarre Harland Williams for an unhinged episode packed with supposedly true stories, bootyholes, and too many farts. Harland kicks things off by reminiscing about fingering calamari and the first time someone touched his arse—with a thermometer. Tom shares the traumatic moment he had to show a friend his infamously hairy sphincter... and yes, he ends up showing Harland too.

Surprisingly, the conversation spirals into absurd territory with erotic drawings, smut searches, fart-catching attempts, a Dominican dick flash, and a deep dive into Enny’s alleged fondness for buttholes. Harland doesn’t disappoint either—he reacts to fart videos, tells a story about dating Madonna, and looks forward to tanning with Tom. The two also talk about creativity, recreational drugs, Harland's distrust of nicotine pouches, the anthems of both Canada and Texas, plus playing doctor, and horseshoes with neck pillows. Oh, and Harland names his favorite dictator. Stick around to find out if Harland ends up eating Tom.

2 Bears, 1 Cave Ep. 290

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Chapters
00:00:00 - Intro
00:02:55 - Arses & Calamari Rings
00:14:34 - So Much Hair
00:26:10 - What's Going On With Canada?
00:31:24 - Measurements, Buzzes, & Vices
00:41:37 - Favorite Dictator
00:51:49 - Dating Madonna
00:55:46 - Clip: Baddie Farts
00:56:49 - Play Back The Tape
00:58:13 - Clip: Fart In One
00:59:29 - Tanning & Tour Dates
01:05:45 - Gas, Gashes, & Gruesome Videos
01:11:48 - Harland Wants To Eat Tom

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