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.

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.

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, Greg, Clark is torn between making a move on her and salvaging his friendship with Greg.

When Jack insults the magazine's I.T. manager, the "techspert" exacts his revenge by leaking office emails that cause the staff to turn on each other.

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.

Jack can't concentrate because of the millennials' distracting juvenile behavior, so Brooke installs cubicles in the bullpen as a remedy.

The millennials' journalistic integrity slips when Jack's nemesis, a former magazine staffer turned famous outdoor reality TV host, returns to guest edit the magazine.

Jack fixates on his relationship with Rachel to the detriment of the magazine and his friends, causing Eddie and Roland to try to break him of the habit.

Jack asks his co-workers to pretend to be his closest friends at a dinner party after his girlfriend becomes concerned by Jack's lack of an inner circle.

Jack dates a millennial to avoid commitment but needs the help of Clark, Emma and Mason to keep up with the girl's exhausting lifestyle.

Jealousy prompts Jack to insult Brooke's fiance at the couple's re-engagement party; the millennials squabble over who should create a slide show for the party.

Mason becomes famous for an investigative coup, but Jack grows jealous and tries to reassert his dominance. Also: Clark has trouble asking out Emma, so he gives her relationship advice about other guys instead.

Roland faces criticism from the leader of the Chicago Adventure Society, who accuses him of faking a story of the expedition that made his career, so Jack, Brooke and the millennials try to clear Roland's name.

The group go camping and Jack tests their survival skills by leaving them alone with their smartphones.

When the human resources department tosses out a rule against inter-office dating, Jack loses his excuse to break up with Amy; Mason comes close to uncovering the romantic history of Jack and Brooke.

Emma quits her job after being refused a raise, making Jack and Roland the magazine's social media managers; Eddie rebrands his bar in an attempt to boost business.

Brooke steps in as Eddie's interim best friend when Jack is unable to help him through the pain of his divorce; a big secret is revealed when Clark, Emma and Mason face off in a fitness tracker challenge to win concert tickets.

After crushing Clark with a brutal performance review, Jack is forbidden by human resources to give the staff any feedback; Emma and Mason try to help Brooke hire a new intern.

The Millennials discover a secret about Jack's love life after they clean out an old storage unit.

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.

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, a renowned adventure reporter, transitions to the roll of desk-bound boss, overseeing a team of 20-something journalists, after the founder of the outdoor magazine he works for decides to go to a web-only publication.