Jess Hilarious recounts a trip to Puerto Rico, Tezlyn Figaro covers Chicago police ties to far-right militia group the Oath Keepers, and the hosts debate age-appropriate Halloween costumes.

Jess Hilarious drops a hot take on 50 Cent, the trio discusses DJ Akademiks and Saucy Santana's feud, and callers debate the pros and cons of reuniting with an ex like Ashanti and Nelly did.

Guest cohost Jess Hilarious and the crew discuss rising homeschooling rates, Jonathan Majors's future with Marvel, Missy Elliott's sit-down with Robin Roberts and more.