ANNA & SYD ON DATING, COMEDY & SIDE QUESTS | In The Slot S3 Ep. 31

Episode Description

In this episode, we’re joined by our newest Barstool coworkers and content creators Anna Coker and Sydney Aiello. With Anna and Syd we talk about their Barstool internships, the dating scene in Chicago, trying standup comedy and their insane side quests. Later in the episode, we get stumped while answering which coworker is the most different off-camera, who in our contacts we’d be mortified to text drunk and what the hottest shoe a guy could wear is. Tune in every Thursday for NEW episodes of In The Slot! In The Slot S3 Ep. 31  - 10/1/26 0:00 - Anna Coker & Sydney Aiello are In The Slot 1:16 - Anna & Syd on their Barstool internships 7:38 - Syd on the Chicago dating scene 11:40 - Anna’s insane side quests 14:14 - Anna & Syd’s awkward encounter with Hank 19:03 - Airport etiquette 21:13 - Anna’s trying out standup comedy 26:12 - Syd & Anna on drama in the Chicago office 27:58 - Would Syd & Anna ever do a Barstool reality show? 31:17 - The Chicago social scene 34:34 - Who would last longer on Surviving Barstool? 35:22 - Texting etiquette 39:43 - Sydney’s marriage pact with Jake Shane 42:13 - Get Stumped 48:00 - Anna & Syd tease their new content idea