Season 1
(2016)
Cast
as Ashley Jack Gordon
as Roland
as Brooke
as Clark Roberts
as Mason
as Emma Cho
as Eddie
Episodes
Pilot 5.2
October 27, 2016
In the series opener, we find Jack, a renowned adventure reporter transitioning to the role of a desk bound boss, overs…
Dating Apps 5.3
November 3, 2016
Clark, Emma and Mason try to help Jack create a profile of himself for an online dating app after his first attempt is …
Step One: Shelter 4.3
November 10, 2016
Jack faces the ultimate test of his survival skills when he’s forced to crash at Clark’s tiny apartment while he search…
You Don't Know Jack 4.0
November 17, 2016
The Millennials discover a huge secret about Jack’s love life when they clean out his decades-old storage unit. Also, C…
No Bad Ideas 4.7
November 24, 2016
Human Resources forbids Jack from giving his staff any feedback at all after he crushes Clark with a brutally honest pe…
Going Deep 5.7
December 1, 2016
When Jack is clueless about how to help Eddie through the pain of his divorce, Brooke steps up to be Eddie’s interim be…
@emma 3.5
December 8, 2016
When Emma quits after being turned down for a raise, Jack and Roland become the magazine’s newest and worst ever social…
Office Romance 5.8
December 15, 2016
Jack regrets convincing Human Resources to toss out a "no inter-office dating" rule when he needs an excuse to break up…
The Mediocre Outdoors 5.2
January 5, 2017
Jack tests the Millennials’ survival skills when he takes them camping for the first time and leaves them alone in the …
The Explorers' Club 3.7
January 12, 2017
When Mather, the president of the Chicago Adventure Society, accuses Roland of faking the story of the expedition that …
Mason Blows Up 4.2
January 19, 2017
Jack tries to reassert his dominance as a reporter after Mason scores an investigative coup that turns him into an over…
Paul's Surprise 5.0
February 9, 2017
When jealousy prompts Jack to insult Brooke’s fiancé, Paul, at the couple’s re-engagement party, he makes things worse …
DTR 6.5
February 16, 2017
When Jack dates a millennial to avoid commitment, he needs Clark, Emma and Mason’s help to keep up with his new girlfri…
Friends Like These 5.3
February 23, 2017
Jack desperately begs his co-workers to pretend to be his closest friends at a dinner party after his lack of an inner …
Relationship Jack 5.0
March 9, 2017
When Jack fixates on his relationship with Rachel to the detriment of the magazine and his friends, Eddie and Roland tr…
Aaron Wolf 4.7
March 27, 2017
Jack watches the millennials’ journalistic integrity slip away when they fall under the spell of his nemesis, Aaron Wol…
Cubicles 4.7
March 30, 2017
When Jack can’t concentrate because of the millennials’ distracting juvenile behavior, Brooke installs cubicles in the …
Party Paul 5.0
April 6, 2017
When Jack takes Brooke’s fiancé, Paul, and Roland out on the town to improve their lukewarm relationship, his plan back…
Ricky Leaks 5.0
April 13, 2017
When Jack insults Ricky, the magazine’s I.T. manager, the “techspert” exacts his revenge by leaking office emails that …
The Heartbreaker 5.3
April 27, 2017
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’…
Roland's Secret 5.3
May 1, 2017
Jack gets caught up in Roland and Brooke’s family drama when they both enlist his help to keep bombshells about their l…
The Company Retreat 5.0
May 8, 2017
At the magazine’s notoriously carnal company retreat, feelings resurface between Jack and Brooke as they work together …