Episode 1

Pilot

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 an outdoor magazine he works for decides to go to a web only publication.

21m

Episode 2

Dating Apps

Clark, Emma and Mason try to help Jack create a profile of himself for an online dating app after his first attempt is disastrous.

21m

Episode 3

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 the millennials their beloved office perks are being taken away due to budget cuts.

21m

Episode 4

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.

21m

Episode 5

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 politically incorrect when they try to help her hire a diverse intern.

21m

Episode 6

Going Deep

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 Mason battle each other in a fitness tracker challenge to win concert tickets.

21m

Episode 7

@emma

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.”

21m

Episode 8

Office Romance

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.

21m

Episode 9

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.

21m

Episode 10

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 his name. Also, Clark is dumbfounded when he notices that Jack seeks Mather’s approval the same way he seeks Jack’s,

21m

Episode 11

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.

21m

Episode 12

Paul's Surprise

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 over their job hierarchy when they can’t decide who should take point on creating a slideshow for the party.

21m

Episode 13

DTR

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.

21m

Episode 14

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, Rachel.

21m

Episode 15

Relationship Jack

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 suffers, Clark steps up to lead the staff and displays a surprising amount of self-confidence.

21m

Episode 16

Aaron Wolf

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.

21m

Episode 17

Cubicles

When Jack can’t concentrate because of the millennials’ distracting juvenile behavior, Brooke installs cubicles in the bullpen.

21m

Episode 18

Party Paul

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.

21m

Episode 19

Ricky Leaks

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.

21m

Episode 20

The Heartbreaker

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. Also, when Emma decides to breakup with her boyfriend, Greg, Clark is torn between making a move on her and salvaging his friendship with Greg.

21m

Episode 21

Roland's Secret

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.

21m

Episode 22

The Company Retreat

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 same way they did five years ago. Also, Roland asks Jack to lead the staff in his absence after he accepts a once-in-a-lifetime opportunity to return to field reporting.

21m