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.
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 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 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.
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.