Seasons & Episodes
Pilot
In the series opener, we find Jack, a renowned adventure reporter transitioning to the role of a desk bound boss, overse
Dating Apps
Clark, Emma and Mason try to help Jack create a profile of himself for an online dating app after his first attempt is d
Step One: Shelter
Jack faces the ultimate test of his survival skills when he’s forced to crash at Clark’s tiny apartment while he sea
You Don't Know Jack
The Millennials discover a huge secret about Jack’s love life when they clean out his decades-old storage unit. Also,
No Bad Ideas
Human Resources forbids Jack from giving his staff any feedback at all after he crushes Clark with a brutally honest per
Going Deep
When Jack is clueless about how to help Eddie through the pain of his divorce, Brooke steps up to be Eddie’s interim b
@emma
When Emma quits after being turned down for a raise, Jack and Roland become the magazine’s newest and worst ever socia
Office Romance
Jack regrets convincing Human Resources to toss out a "no inter-office dating" rule when he needs an excuse to break up
The Mediocre Outdoors
Jack tests the Millennials’ survival skills when he takes them camping for the first time and leaves them alone in the
The Explorers' Club
When Mather, the president of the Chicago Adventure Society, accuses Roland of faking the story of the expedition that m
Mason Blows Up
Jack tries to reassert his dominance as a reporter after Mason scores an investigative coup that turns him into an overn
Paul's Surprise
When jealousy prompts Jack to insult Brooke’s fiancé, Paul, at the couple’s re-engagement party, he makes things wo
DTR
When Jack dates a millennial to avoid commitment, he needs Clark, Emma and Mason’s help to keep up with his new girlfr
Friends Like These
Jack desperately begs his co-workers to pretend to be his closest friends at a dinner party after his lack of an inner c
Relationship Jack
When Jack fixates on his relationship with Rachel to the detriment of the magazine and his friends, Eddie and Roland try
Aaron Wolf
Jack watches the millennials’ journalistic integrity slip away when they fall under the spell of his nemesis, Aaron Wo
Cubicles
When Jack can’t concentrate because of the millennials’ distracting juvenile behavior, Brooke installs cubicles in t
Party Paul
When Jack takes Brooke’s fiancé, Paul, and Roland out on the town to improve their lukewarm relationship, his plan ba
Ricky Leaks
When Jack insults Ricky, the magazine’s I.T. manager, the “techspert” exacts his revenge by leaking office emails
The Heartbreaker
Roland's Secret
Jack gets caught up in Roland and Brooke’s family drama when they both enlist his help to keep bombshells about their
The Company Retreat
At the magazine’s notoriously carnal company retreat, feelings resurface between Jack and Brooke as they work together