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In the series opener, we find Jack, a renowned adventure reporter transitioning to the role of a desk bound boss, overseeing a team of twentysomething journalists, after the founder of .. show full overview
Clark, Emma and Mason try to help Jack create a profile of himself for an online dating app after his first attempt is disastrous.
Step One: Shelter
Jack faces the ultimate test of his survival skills when he's forced to crash at Clark's tiny apartment while he searches for a place of his own. Also, Roland sticks Brooke with telling .. show full overview
You Don't Know Jack
The Millennials discover a huge secret about Jack's love life when they clean out his decades-old storage unit. Also, Clark and Mason use Jack's memorabilia to throw an epic '90s-themed party at Eddie's bar.
No Bad Ideas
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 .. show full overview
When Jack is clueless about how to help Eddie through the pain of his divorce, Brooke steps up to be Eddie's interim best friend. Also, a colossal secret comes out when Clark, Emma and .. show full overview
When Emma quits after being turned down for a raise, Jack and Roland become the magazine's newest and worst ever social media managers. Also, in a misguided attempt to boost business, Eddie re-brands his bar as "magic-themed".
Jack regrets convincing Human Resources to toss out a "no inter-office dating" rule when he needs an excuse to break up with his co-worker, Amy. Also, Mason closes in on uncovering Jack and Brooke's romantic history.
The Mediocre Outdoors
Jack tests the Millennials’ survival skills when he takes them camping for the first time and leaves them alone in the woods without their smartphones.
The Explorers’ Club
When Mather, 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 .. show full overview
Mason Blows Up
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.
When jealousy prompts Jack to insult Brooke's fiancé, Paul, at the couple's re-engagement party, he makes things worse by repeatedly botching his apology. Also, the millennials squabble .. show full overview
When Jack dates a millennial to avoid commitment, he needs Clark, Emma and Mason's help to keep up with his new girlfriend, Kaylie, and her exhausting lifestyle.
Friends Like These
Jack desperately begs his co-workers to pretend to be his closest friends at a dinner party after his lack of an inner circle begins to concern his girlfriend. However, he soon regrets .. show full overview
When Jack fixates on his relationship with Rachel to the detriment of the magazine and his friends, Eddie and Roland try to break him of his obsession habit. Also, as Jack's work .. show full overview
Jack watches the millennials’ journalistic integrity slip away when they fall under the spell of his nemesis, Aaron Wolf, a former magazine staffer turned famous outdoor reality TV host who returns to guest edit the magazine.
Jack can't concentrate because of the millennials' distracting juvenile behavior, so Brooke installs cubicles in the bullpen as a remedy.
When Jack takes Brooke’s fiancé, Paul, and Roland out on the town to improve their lukewarm relationship, his plan backfires when Paul gets tipsy and goes missing,
When Jack insults Ricky, the magazine's I.T. manager, the "techspert" exacts his revenge by leaking office emails that cause the staff to turn on each other.
Jack sets up a double date to get Eddie out of a post-divorce rut, but the night gets awkward when they run into Eddie's ex-wife. Emma decides to break up with her boyfriend, and Clark is torn between dating her and saving his friendship with Greg.
Jack gets caught up in Roland and Brooke's family drama when they both enlist his help to keep bombshells about their love lives from each other.
The Company Retreat
In the season finale, at the magazine’s notoriously carnal company retreat, feelings resurface between Jack and Brooke as they work together to help Clark finally hook up with Emma – the .. show full overview
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