Jake works on an investigation involving philanthropic civic leader Lucas Wint much to the chagrin of Commissioner Podolski. Meanwhile, Charles is devastated over breaking up with Vivian, and Rosa and Terry try to cheer him up. Gina incorporates emoji into her everyday speech.
Jake walks out of a bar bathroom heavily drunk and sits at the bar ordering drinks for everyone. One the patrons asks him what the occasion is, and Jake reveals that he's celebrating the fact that he just got fired from the NYPD.
It cuts to a week ago where Charles is in all black and heavily depressed since Vivian and he ended their engagement. Jake is then called into Holt's office where he coldly reunites with Commissioner Podolski. It turns out Jake has been investigating civic leader Lucas Wint who he believes might be laundering money to drug dealers. Podolski doesn't believe it, even adding in that Wint has publicly filed a complaint against Jake for harassing him. Since Jake has very little evidence, Holt and Podolski order him to drop this case. Meanwhile, the rest of the squad discuss what they can do to cheer up Charles.
Jake, however, decides to go against orders and brings Amy with him to spy on Wint, only to get caught. As punishment, Jake is suspended for six months and will have to go in front of a hearing to decide his fate in the NYPD. On the day of the hearing, Jake reveals that Amy, who believes that Jake is on to something, found an informant that reveals that he brings money to Wint that he then adds into their account book for donations. Holt reluctantly decides to trust Jake on this but decides to be apart of this case as well. Terry tells the rest of the squad that they will have to stall the hearing to give them more time. Rosa and Terry try different ways to cheer up Charles, but none of them yield success.
Meanwhile, Jake, Amy, and Holt go to Judge Mindel and manage to get written permission to search the community center for the account book thanks to Holt's flirting. They then get dress clothes for an amateur ball dancing competition to blend in. While Amy fakes an accident, Jake manages to get enough evidence to prove his case. Holt, however, gets a call tells him not to show the evidence and asks him to do something. Jake then does what Holt told him, and gets himself fired from the NYPD. It turns out that Jake stumbled onto an FBI investigation of Lucas Wint, with the assumption that Wint has ties to the Ianucci Crime Family. The family also has moles in the NYPD, and the head agents invite Jake to go undercover for them and take the family down. Jake agrees, and says goodbye to everyone and even tells Amy that he has feelings for her, confusing her a bit.
It then cuts back to the intro where it's revealed that the person Jake was talking to is a member of the Ianucci Family. Charles gets better when Rosa reveals that she never dated anyone good, and they get drunk. The next morning, however, it's revealed that he slept with Gina..
|Andy Samberg||...||Jake Peralta|
|Stephanie Beatriz||...||Rosa Diaz|
|Terry Crews||...||Terry Jeffords|
|Melissa Fumero||...||Amy Santiago|
|Joe Lo Truglio||...||Charles Boyle|
|Chelsea Peretti||...||Gina Linetti|
|Andre Braugher||...||Captain Ray Holt|
|Dirk Blocker||...||Michael Hitchcock|
|Joel McKinnon Miller||...||Norm Scully|
|Marilu Henner||...||Vivian Ludley|
|Ian Roberts||...||Lucas Wint|
|James M. Connor||...||Deputy Commissioner Podolski|
|Stella Angelova||...||Dancer Wit Holt|
|Alton Clemente||...||Leo Ianucci|
|Judith Scarpone||...||Judge Mindel|
|Benjamin Steinberg||...||Young Jake|
|Chris Flanders||...||Gilbert (Emcee)|
|Denell Johnson||...||Allen (Tough Guy)|
|Adam Lieberman||...||Agent Nathan Clarke|
|Tiffany Martin||...||Young Jenny Gildenhorn|
- Gina compares the all black outfit Charles wears after his breakup to those worn by the characters from the film "The Matrix."
- At Lucas Wint's weekly basketball game, Jake shouts "Kobe" when he tries to shoot the ball. Kobe Bryant is a succesful professional basketball player.
- Gina describes an emoji as "Cat doing 'Home Alone' face." A famous scene from Home Alone has the lead actor putting his hands on either side of his face and screaming.
- During his hearing, Jake shouts, "You can't handle the me!" in reference to a famous line from the movie "A Few Good Men." The actual line, spoken by a military officer on trial, is "You can't handle the truth!"
- Jake uses the expression "Eyes closed, head first, cant lose." This is in reference to the mantra used by characters on the TV show 'Friday Night Lights.' The actual phrase is "Clear eyes, full hearts, can't lose."
- The episode was directed by Akiva Schaffer, a member of The Lonely Island with Andy Samberg and Jorma Taccone.
- Alton Clemente is credited as playing Johnny Ianucci, however, in the episode, he introduces himself as Leo.
- In this episode, Holt had said all of his breakups have been completely mutual. But later in episode Ava, Holt said things did not end well between his ex-boyfriend, Frederick, and him.