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Elsewhere, Clark, Emma, and Mason have to wear fitness watches for a future article, and have a contest to see who can move the least.The heartbeat monitor on Clark's watch hints that he has a crush on Emma.Jack Gordon has made a name for himself as an adventure reporter for the magazine Outdoor Limits.His days of exploring the world end when the magazine's founder, Roland, announces its move to web-only publishing and assigns Jack to its headquarters in Chicago to supervise the millennials who make up its online team.As Jack struggles adjusting to his new life working exclusively indoors, Outdoor Limits is making budget cuts, and Brooke says they can't afford to have him living in posh hotels anymore.While Jack searches for a place to live, Clark kindly offers his tiny apartment as a place for his supervisor to crash.
Jack Gordon, a field reporter who has traveled the world to write stories for Outdoor Limits magazine, learns that the publication has gone to an online-only format.
Jack admits he and Jessie were together for two years, and she broke his heart when he returned from an assignment and found her gone.
As Emma helps Jack track down Jessie, Clark and Mason decide to use artifacts found in Jack's storage unit to throw a 90's party at Eddie's bar.
Clark, Emma and Mason try to give Jack advice, but it is no use. After Jack has a meal with Rachel and some of her friends, she says she'd like to meet his friends.
Other than Eddie, whom Rachel already knows, Jack realizes his old friends are either still out seeking adventures or have died in related accidents.
Jack does so, but he ad-libs several insulting jokes about Paul, making his co-workers question if he has feelings for Brooke.