prop-es:shortsummary
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- 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. Meanwhile, Brooke is tired of being a "Bad Cop" all the time, and digs hard into Roland to help her father find his killer instinct. (es)
- Clark wants advice from Jack on how to get a date with Emma, but first Jack has to get HR to lift the ban on interoffice dating. Jack is successful, but he regrets it after he sleeps with Amy from the accounting department and determines she is too boring to continue seeing. In a twist, Jack now needs advice from Clark on how to break up with Amy easily. (es)
- Jack is taking all the hardcore writing assignments for himself, and assigning soft stories to Mason and Clark. While pursuing one of his assignments, Mason stumbles upon an abducted tiger, leading to his story and catch phrase blowing up on social media. Feeling challenged, Jack works all night on one of his stories which also becomes a hit, but gets angry when Roland suggests that the red-hot Mason represent it for the magazine. Meanwhile, Clark inadvertently pushes Emma and her new boyfriend closer together. (es)
- While helping Jack clean out his storage unit, the group finds an old answering machine with evidence that Jack once lived with a woman named Jessie. 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. (es)
- Jack and Brooke hold a meeting with Emma to scold her about her tardiness and work habits, causing Emma to quit. Jack and Roland try to take over Emma's role as social media manager, but fail badly. They then hire the seemingly qualified Maybelle for the position, but that soon backfires. They finally have to plead with Emma to come back. (es)
- Jack takes the millennial staff to a meeting at the Chicago Adventure Society to hear Roland retell the mountain climbing tale that inspired Jack's career choice. But Roland is shunned when the club president reveals newly-discovered evidence that indicates Roland lied about details of the adventure. Meanwhile, a girl Emma is mentoring quits following her on Twitter, making Emma feel like she's already ceased to be relevant at age 26. (es)
- Jack's critical attitude towards Clark's lackluster work ethic causes management to take action against him, forcing him to say only positive things about Clark. Meanwhile, Brooke chooses Emma and Mason to find a new intern that meets the company's ethnic diversity standards. (es)
- Jack, who has never had a problem getting a date, finds the world of online dating apps to be considerably different than meeting women in the traditional manner. (es)
- Brooke accuses Jack of not being a supportive friend when he can't see how Eddie is hurting after learning his divorce is final. In her own life, Brooke learns her engagement registry at a department store has been cancelled after three-plus years, making her wonder if things with her fiancé Paul will ever progress. 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. (es)
- Brooke introduces Jack to her fiancé Paul , and they ask Jack if he will read Roland's speech at their re-engagement party because Roland can't be there. Jack does so, but he ad-libs several insulting jokes about Paul, making his co-workers question if he has feelings for Brooke. Meanwhile, Clark, Emma and Mason argue over which of their three positions has leadership over the others. (es)
- After Jack meets blind date Rachel at the bar and gives the old "not looking for a commitment" speech, the two mutually agree to end things before they start. Jack then meets a hard-partying millennial named Kaylie and starts going out with her, but can't keep up. Clark, Emma and Mason try to give Jack advice, but it is no use. Jack then contacts Rachel and the two try again. (es)
- When Clark, Emma, and Mason are tasked with testing a new line of camping products, Jack decides he needs to teach the inexperienced millennials about camping the way Roland taught him and Brooke: by leaving them to fend for themselves in the wilderness while he goes to a posh resort nearby. Brooke clashes with Jack and her father, insisting they need to make camping fun for the millennials because they aren't equipped to learn the way she and Jack did. (es)
- 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. Meanwhile, Brooke is tired of being a "Bad Cop" all the time, and digs hard into Roland to help her father find his killer instinct. (es)
- Clark wants advice from Jack on how to get a date with Emma, but first Jack has to get HR to lift the ban on interoffice dating. Jack is successful, but he regrets it after he sleeps with Amy from the accounting department and determines she is too boring to continue seeing. In a twist, Jack now needs advice from Clark on how to break up with Amy easily. (es)
- Jack is taking all the hardcore writing assignments for himself, and assigning soft stories to Mason and Clark. While pursuing one of his assignments, Mason stumbles upon an abducted tiger, leading to his story and catch phrase blowing up on social media. Feeling challenged, Jack works all night on one of his stories which also becomes a hit, but gets angry when Roland suggests that the red-hot Mason represent it for the magazine. Meanwhile, Clark inadvertently pushes Emma and her new boyfriend closer together. (es)
- While helping Jack clean out his storage unit, the group finds an old answering machine with evidence that Jack once lived with a woman named Jessie. 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. (es)
- Jack and Brooke hold a meeting with Emma to scold her about her tardiness and work habits, causing Emma to quit. Jack and Roland try to take over Emma's role as social media manager, but fail badly. They then hire the seemingly qualified Maybelle for the position, but that soon backfires. They finally have to plead with Emma to come back. (es)
- Jack takes the millennial staff to a meeting at the Chicago Adventure Society to hear Roland retell the mountain climbing tale that inspired Jack's career choice. But Roland is shunned when the club president reveals newly-discovered evidence that indicates Roland lied about details of the adventure. Meanwhile, a girl Emma is mentoring quits following her on Twitter, making Emma feel like she's already ceased to be relevant at age 26. (es)
- Jack's critical attitude towards Clark's lackluster work ethic causes management to take action against him, forcing him to say only positive things about Clark. Meanwhile, Brooke chooses Emma and Mason to find a new intern that meets the company's ethnic diversity standards. (es)
- Jack, who has never had a problem getting a date, finds the world of online dating apps to be considerably different than meeting women in the traditional manner. (es)
- Brooke accuses Jack of not being a supportive friend when he can't see how Eddie is hurting after learning his divorce is final. In her own life, Brooke learns her engagement registry at a department store has been cancelled after three-plus years, making her wonder if things with her fiancé Paul will ever progress. 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. (es)
- Brooke introduces Jack to her fiancé Paul , and they ask Jack if he will read Roland's speech at their re-engagement party because Roland can't be there. Jack does so, but he ad-libs several insulting jokes about Paul, making his co-workers question if he has feelings for Brooke. Meanwhile, Clark, Emma and Mason argue over which of their three positions has leadership over the others. (es)
- After Jack meets blind date Rachel at the bar and gives the old "not looking for a commitment" speech, the two mutually agree to end things before they start. Jack then meets a hard-partying millennial named Kaylie and starts going out with her, but can't keep up. Clark, Emma and Mason try to give Jack advice, but it is no use. Jack then contacts Rachel and the two try again. (es)
- When Clark, Emma, and Mason are tasked with testing a new line of camping products, Jack decides he needs to teach the inexperienced millennials about camping the way Roland taught him and Brooke: by leaving them to fend for themselves in the wilderness while he goes to a posh resort nearby. Brooke clashes with Jack and her father, insisting they need to make camping fun for the millennials because they aren't equipped to learn the way she and Jack did. (es)
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