On her day off in Chicago, Kristin checks in on her Uncommon James store followed by a dinner with friends that takes a turn; her entourage heads to Boston where Camille Kostek joins her on stage.

Kristin has to quickly regroup for her second show of the night in her hometown of Chicago; Harry Jowsey helps Kristin reset the vibe; a blast from Kristin's past makes her question why she's been drawn to certain men.

Night two of the tour is a big one for Kristin as she gears up for the Windy City and a high school reunion like no other with her friends from Laguna Beach; the old classmates catch up and spill some 20+ year secrets.

Kristin Cavallari is fed up with clickbait headlines so she's taking matters into her own hands; first in Atlanta with guest Kim Zolciak, where they discuss what it's like to be a mom while going through a public divorce.