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.

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.

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.

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

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.