At the magazine's company retreat, feelings resurface between Jack and Brooke as the two try to help Clark hook up with Emma; Roland accepts an opportunity to return to field reporting.
Jack is caught up in Roland and Brooke's family drama when they each ask for help hiding secrets about their love lives.
Jack sets up a double date to get Eddie out of a post-divorce rut; Emma decides to break up with her boyfriend.
After Jack insults Ricky, the magazine's IT manager, Ricky's actions cause everyone on the staff to turn on each other.
Jack takes Brooke's fiancé, Paul, and Roland out for a night on the town; Paul gets tipsy and goes missing.
Jack can't concentrate because of the millennials' distracting juvenile behavior, so Brooke installs cubicles in the bullpen as a remedy.
The millennials' journalistic integrity slips when Jack's nemesis, a former magazine staffer turned famous outdoor reality TV host, returns to guest edit the magazine.
Jack fixates on his relationship with Rachel to the detriment of the magazine and his friends, causing Eddie and Roland to try to break him of the habit.
Jack asks his co-workers to pretend to be his closest friends at a dinner party after his girlfriend becomes concerned by Jack's lack of an inner circle.
Jack dates a millennial to avoid commitment but needs the help of Clark, Emma and Mason to keep up with the girl's exhausting lifestyle.
Jealousy prompts Jack to insult Brooke's fiance at the couple's re-engagement party; the millennials squabble over who should create a slide show for the party.
An investigative coup turns Mason into an overnight celebrity, causing Jack to try and reassert his dominance; due to his low self-esteem, Clark offers Emma relationship advice about other men rather than asking her out.
When an adventure society's president accuses Roland of faking an expedition, Jack and the gang work to clear his name.
Jack tests the gang's survival skills by taking them on a camping trip and leaving them alone in the woods without their cellphones.
When the human resources department tosses out a rule against inter-office dating, Jack loses his excuse to break up with Amy; Mason comes close to uncovering the romantic history of Jack and Brooke.
Emma quits her job after being refused a raise, making Jack and Roland the magazine's social media managers; Eddie rebrands his bar in an attempt to boost business.
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.
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.
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.
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.
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, 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.