Jack is a renowned adventure reporter transitioning to the role of a desk bound boss, overseeing a team of twentysomething journalists, after the founder of an outdoor magazine he works for decides to go to a web only publication.
Clark, Emma and Mason try to help Jack create a profile of himself for an online dating app after his first attempt is disastrous.
Jack faces the ultimate test of his survival skills when he's forced to crash at Clark's tiny apartment while he searches for a place of his own. Also, Roland sticks Brooke with telling the millennials their beloved office perks are being taken away due to budget cuts.
The Millennials discover a huge secret about Jack's love life when they clean out his decades-old storage unit. Also, Clark and Mason use Jack's memorabilia to throw an epic '90s-themed party at Eddie's bar.
Human Resources forbids Jack from giving his staff any feedback at all after he crushes Clark with a brutally honest performance review. Also, Emma and Mason call out Brooke for being politically incorrect when they try to help her hire a diverse intern.
When Jack is clueless about how to help Eddie through the pain of his divorce, Brooke steps up to be Eddie's interim best friend. Also, a colossal secret comes out when Clark, Emma and Mason battle each other in a fitness tracker challenge to win concert tickets.
When Emma quits after being turned down for a raise, Jack and Roland become the magazine's newest and worst ever social media managers. Also, in a misguided attempt to boost business, Eddie re-brands his bar as "magic-themed".
Jack regrets convincing Human Resources to toss out a "no inter-office dating" rule when he needs an excuse to break up with his co-worker, Amy. Also, Mason closes in on uncovering Jack and Brooke's romantic history.
Jack tests the Millennials' survival skills when he takes them camping for the first time and leaves them alone in the woods without their smartphones.
When Mather, the president of the Chicago Adventure Society, accuses Roland of faking the story of the expedition that made his career, Jack, Brooke and the millennials team up to clear his name. Also, Clark is dumbfounded when he notices that Jack seeks Mather's approval the same way he seeks Jack's,
Jack tries to reassert his dominance as a reporter after Mason scores an investigative coup that turns him into an overnight celebrity. Also, Clark's low self-esteem causes him to give Emma relationship advice about other guys.
When jealousy prompts Jack to insult Brooke's fiancé, Paul, at the couple's re-engagement party, he makes things worse by repeatedly botching his apology. Also, the millennials squabble over their job hierarchy when they can't decide who should take point on creating a slideshow for the party.
When Jack dates a millennial to avoid commitment, he needs Clark, Emma and Mason's help to keep up with his new girlfriend, Kaylie, and her exhausting lifestyle.
Jack desperately begs his co-workers to pretend to be his closest friends at a dinner party after his lack of an inner circle begins to concern his girlfriend. However, he soon regrets asking for their help after they behave awkwardly in her presence.
When Jack fixates on his relationship with Rachel to the detriment of the magazine and his friends, Eddie and Roland try to break him of his obsession habit. Also, as Jack's work suffers, Clark steps up to lead the staff and displays a surprising amount of self-confidence.
Jack watches the millennials' journalistic integrity slip away when they fall under the spell of his nemesis, Aaron Wolf, a former magazine staffer turned famous outdoor reality TV host who returns to guest edit the magazine.
Jack can't concentrate because of the millennials' distracting juvenile behavior, so Brooke installs cubicles in the bullpen as a remedy.
When Jack takes Brooke's fiancé, Paul, and Roland out on the town to improve their lukewarm relationship, his plan backfires when Paul gets tipsy and goes missing,.
When Jack insults Ricky, the magazine's I.T. manager, the "techspert" exacts his revenge by leaking office emails that cause the staff to turn on each other.
Jack sets up a double date to get Eddie out of a post-divorce rut, but the night gets awkward when they run into Denise, Eddie's ex-wife. Also, when Emma decides to breakup with her boyfriend, Clark is torn between making a move on her and salvaging his friendship with Greg.
Jack gets caught up in Roland and Brooke's family drama when they both enlist his help to keep bombshells about their love lives from each other.
At the magazine's notoriously carnal company retreat, feelings resurface between Jack and Brooke as they work together to help Clark finally hook up with Emma - the same way they did five years ago. Also, Roland asks Jack to lead the staff in his absence after he accepts a once-in-a-lifetime opportunity to return to field reporting.