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1-8 of 8
- 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.
- When Jack is unable to help Eddie get through the pain of his divorce, Brooke steps up to be his friend.
- Clark, Emma and Mason must intervene when Jack decides to try online dating and creates the worst profile ever for himself.
- 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.
- Jack puts his survival skills to the test when he has to crash at Chad's tiny apartment.
- 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 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.