Honestly Cavallari: The Headline Tour

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 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.

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's alleged party girl ways lead to some charming headlines with Bravo's Craig and Austen; Kristin attempts to clear up the gossip with the "Southern Charm" cast in Boston.