On Brooklyn Nine-Nine Season 2 Episode 20, Jake and Charles try to catch a robbery suspect, but Jake gets hurt during the chase and is not cleared for active duty or field work. At Jake's insistence, Terry agrees to let him stay at the precinct to work the case on the condition that he doesn't leave his desk. However, Jake promptly ignores these orders, and gets hurt again in the office. Terry orders him to take a week off.

Four days later, Jake takes Charles on vacation to Atlantic City, a ruse to stake out the robbery suspect.  Charles calls Terry in from NYC to Atlantic City to stop Jake from doing anything that might get him more hurt. While waiting for Atlantic City PD to take over, Jake chases the guy on foot and gets hit by a car.

Jake in the hospital, confesses that he once went on vacation during a case and two civilians got killed because of the drug dealer he was chasing. His workaholic nature stems from swearing never to take time off during a case again.

Meanwhile, Marcus and Kevin arrange for Holt and Rosa to all have dinner together at Holt's house, jeopardizing their plan to keep completely out of each other's personal lives. Holt invites "intimacy buffers" - namely, Gina and Amy - to the dinner in order to keep things light.  However, Gina and Amy arrive too late to be of any use, and instead spend the night out drinking.

At the dinner, Holt and Rosa are forced to make small talk.  However, in a panicked moment when being asked about her family life, Rosa reveals to Holt that she may be pregnant.  Holt advises her to take a pregnancy test, which turns out negative.  Holt and Rosa decide that having some personal interaction may not be a bad thing.