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

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 is forced to crash at Clark's tiny apartment until he can find his own place; Brooke has to tell the gang that the office perks are being taken away due to budget cuts.

The team cleans out Jack's old storage unit, discovering secrets about his love life in the process; Clark and Mason host a '90s-themed party at Eddie's bar.

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.

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.