In the series opener, we find Jack, a renowned adventure reporter transitioning to the role of a desk bound boss, ove...

Clark, Emma and Mason try to help Jack create a profile of himself for an online dating app after his first attempt i...

Jack faces the ultimate test of his survival skills when he’s forced to crash at Clark’s tiny apartment while he sear...

The Millennials discover a huge secret about Jack’s love life when they clean out his decades-old storage unit. Also,...

Human Resources forbids Jack from giving his staff any feedback at all after he crushes Clark with a brutally honest ...

When Jack is clueless about how to help Eddie through the pain of his divorce, Brooke steps up to be Eddie’s interim ...

When Emma quits after being turned down for a raise, Jack and Roland become the magazine’s newest and worst ever soci...

Jack regrets convincing Human Resources to toss out a "no inter-office dating" rule when he needs an excuse to break ...

Jack tests the Millennials’ survival skills when he takes them camping for the first time and leaves them alone in th...

When Mather, the president of the Chicago Adventure Society, accuses Roland of faking the story of the expedition tha...

Jack tries to reassert his dominance as a reporter after Mason scores an investigative coup that turns him into an ov...

When jealousy prompts Jack to insult Brooke’s fiancé, Paul, at the couple’s re-engagement party, he makes things wors...

When Jack dates a millennial to avoid commitment, he needs Clark, Emma and Mason’s help to keep up with his new girlf...

Jack desperately begs his co-workers to pretend to be his closest friends at a dinner party after his lack of an inne...

When Jack fixates on his relationship with Rachel to the detriment of the magazine and his friends, Eddie and Roland ...

Jack watches the millennials’ journalistic integrity slip away when they fall under the spell of his nemesis, Aaron W...

When Jack can’t concentrate because of the millennials’ distracting juvenile behavior, Brooke installs cubicles in th...

When Jack takes Brooke’s fiancé, Paul, and Roland out on the town to improve their lukewarm relationship, his plan ba...

When Jack insults Ricky, the magazine’s I.T. manager, the “techspert” exacts his revenge by leaking office emails tha...

Jack sets up a double date to get Eddie out of a post-divorce rut, but the night gets awkward when they run into Eddi...

Jack gets caught up in Roland and Brooke’s family drama when they both enlist his help to keep bombshells about their...

At the magazine’s notoriously carnal company retreat, feelings resurface between Jack and Brooke as they work togethe...