In the series opener, we find Jack, a renowned adventure reporter transitioning to the role of a desk bound boss, overseeing a team of...

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 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...

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...

Human Resources forbids Jack from giving his staff any feedback at all after he crushes Clark with a brutally honest performance review. Also, Emma...

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...

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,...

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....

Jack tests the Millennials’ survival skills when he takes them camping for the first time and leaves them alone in the woods without their...

When Mather, the president of the Chicago Adventure Society, accuses Roland of faking the story of the expedition that made his career, Jack, Brooke...

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...

When jealousy prompts Jack to insult Brooke’s fiancé, Paul, at the couple’s re-engagement party, he makes things worse by...

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...

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...

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...

Jack watches the millennials’ journalistic integrity slip away when they fall under the spell of his nemesis, Aaron Wolf, a former magazine...

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

When Jack takes Brooke’s fiancé, Paul, and Roland out on the town to improve their lukewarm relationship, his plan backfires when Paul...

When Jack insults Ricky, the magazine’s I.T. manager, the “techspert” exacts his revenge by leaking office emails that cause the...

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...

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...

At the magazine’s notoriously carnal company retreat, feelings resurface between Jack and Brooke as they work together to help Clark finally...