Jake is requested to act as a negotiator for a hostage situation at a jewelry store only to find out that it's a set-up from Doug Judy, who asks for his help to take down a dangerous criminal in order to rescue Judy's mother. Amy and Gina try to help Charles out with his new food truck as the stress of his new business and perfectionist attitude seems to be getting to him. When a member of the Police Commissioner selection committee decides to interview Hitchcock about Holt's qualities, Holt and Terry train him to be less disgusting and more professional.
Episode Tropes:
- Bad Boss: Charles is too demanding to Amy and Gina when running the food truck. It's later revealed that Charles' previous employees quit because of this.
- Body Horror: Scully's health is so bad that he can stop his own heart at will.
- Chronic Backstabbing Disorder: Lampshaded by Rosa; she calls Doug Judy a scorpion that will sting Jake, a "naive little frog," and she's proven right. However, it's downplayed, in that Doug still won't ruin Jake's career, and sends the diamonds back so Jake can keep his badge.
- Chronic Villainy: Zigzagged. Doug is only brought back into a life of crime by a threat against his mother's life, and he does help Jake take down a major drug dealer, but he makes clear, at the end, that he just wasn't happy with a non-criminal life.
- Epic Fail: Dennis Kole had a 98 percent failure rate with talking down jumpers; the last guy jumped, but he survived due to a woman below breaking his fall. The woman died, as a result.
- Genre Savvy: Rosa mentions that her dad taught her a folktale about a frog helping a scorpion across a river, and it ended with the scorpion stinging the frog and drowning them both. She relates it to Jake's situation with Doug Judy. Doug later admits she's right and that he is a scorpion who has to "scorp".
- Idiot Ball: Rosa going along with Jake's plan to help Doug Judy save his mother, rather than arresting him. She points out that Jake is a "naive little frog" that's going to get stung by a scorpion like Doug Judy, and they'll both drown. But she still helps Doug Judy escape the hostage situation by calling in Scully, who fakes a medical emergency.
- I Have Your Wife: Doug Judy ran into bad company with a drug kingpin and the kingpin is holding his mother hostage, or at least threatening her life, unless Doug Judy pays him. Jake agrees to help on the condition that Doug Judy surrenders.
- Jerkass: The original negotiator, Dennis Kole. He's incredibly rude to Jake from the first moment they meet, mocks the suicidal people who he tries (unsuccessfully) to save, and claims that the sole purpose of hostage negotiation is to kill the person you're negotiating with. He's also very open about the fact that he doesn't care about catching criminals, his only motivation is to get a promotion.
- Jurisdiction Friction: Dennis Kole, the hostage negotiator assigned to the case, is angry that his first actual hostage negotiation is taken over by Jake. That frustration might be understandable, if the guy weren't so personally unpleasant (see Jerkass, above).
- No Celebrities Were Harmed: The pressure of running a food truck gets Charles to start channeling Gordon Ramsay's trademark abrasiveness.
- No Sympathy:
- Downplayed; Rosa humors Jake briefly with feigned sympathy when her suspicions that Doug Judy will screw Jake over prove correct, rather than saying I Told You So.
- Averted. Holt is sympathetic that Jake trusted Doug Judy because the latter is charismatic and conniving, and Holt tried to vouch for Jake when Doug Judy went missing with the diamonds. Even so, he's Brutally Honest in that unless Jake gets the diamonds and Doug Judy, he'll probably lose his badge.
- Once a Season: Lampshaded when Jake mentions that he runs into Doug Judy about once a year.
- Parallel Porn Titles: Hitchcock is not familiar with My Fair Lady, but its porn parody My Bare Lady with Eliza DoEverybody and Leroy Pipe.
- Pygmalion Plot: Holt and Terry trying to make Hitchcock a more presentable officer for the interview. Hitchcock recognizes it from My Fair Lady... or rather, its porn parody My Bare Lady.
- Surprisingly Realistic Outcome: Jake risks losing his license when Doug Judy runs off with the diamonds.
- The Tape Knew You Would Say That: The video Doug Judy leaves for Jake at the karaoke place anticipates his side of the conversation...mostly. The timing is off in a couple places, and it generally assumes that Jake will react much more positively than he really does. Jake still winds up singing "What's Up" along with the video.
- Wrong Genre Savvy: Holt and Terry cite My Fair Lady when helping Hitchcock clean up his act. They then suggest that Hitchcock could be like that all the time, since Eliza Doolittle didn't go back to being a flower girl. He responds by citing what happens in My Bare Lady, which gives Holt and Terry Brain Bleach. They decide to leave Hitchcock alone.
- Jake also plays out his entire friendship with Doug like they're in a cinematic romance. After he's betrayed, he reacts exactly like someone who'd be abandoned by their lover.
- You Keep Using That Word: Kole repeatedly starts sentences by gruffly saying "lemme give you some advice", then makes a statement rather than actually advising anything.Kole: Lemme give you some advice: I don't care.Jake: You should look up the word "advice" in the dictionary, I think you might be surprised.
