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Jack, a renowned adventure reporter, transitions to the role 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.

Clark, Emma and Mason must intervene when Jack decides to try online dating and creates the worst profile ever for himself.

Jack puts his survival skills to the test when he has to crash at Chad's tiny apartment.

The Millenials uncover a secret about Jack's love life while cleaning out his storage unit. In the meantime, Clark and Mason use Jack's old stuff to throw a '90s 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 unable to help Eddie get through the pain of his divorce, Brooke steps up to be his friend.

When Emma quits after being turned down for a raise, Jack and Roland take over as the magazine's new social media directors.

Jack regrets making Human Resources toss out a rule against dating in the office when he needs an excuse to break up with a co-worker.

The Millennials' survival skills are tested when Jack takes them camping and leaves them in the woods without their smartphones.

When Mather (Barry Bostwick), 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 instead of asking her out himself.

Jack insults Brooke's fiance at their re-engagement party out of jealousy; the millenials argue over who should make a slideshow for the party.

Jake dates a millennial to avoid commitment, but turns to Clark, Emma and Mason to keep up with her.

Jack begs his co-workers to be his best friends when his girlfriend expresses her concern about his lack of an inner circle.

Eddie and Roland try to help Jack break his obsession habit when he fixated on his relationship with Rachel.

Aaron Wolf, a former co-worker of Jack's, returns to the magazine as a guest editor.

Brooke installs cubicles in the bullpen when Jack gets distracted by the millenials' behavior.

Jack takes Brooke's fiancee, Paul, and Roland out on the town to fix their relationship, but the plan backfires when Paul goes missing.

The magazine's I.T. manager, Ricky, leaks office emails to get revenge for Jack for insulting him.

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 (Essence Atkins), Eddie's ex-wife. Also, when Emma decides to breakup with her boyfriend, Greg (Andy Ridings), 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 lives from each other.

At the magazine's carnal company retreat, feelings resurface between Jack and Brooke as they work together to help Clark finally hook up with Emma. 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.