Arguably the most well-known and popular running gag in Brooklyn Nine-Nine, the Halloween heist just gets more outrageous with each season. First Jake wins, followed by Holt in Season 2, then Amy sneaks around and steals the whole thing in Season 3, opening the field for every member of the Nine-Nine. After Gina’s non-detective win in Season 4, Amy, Holt, and Jake are all determined to win the Season 5 heist in HalloVeen, which requires them to be in possession of a wrestler’s championship belt.
The episode takes the usual twists and turns, with characters betraying each other left and right while Amy, Jake, and Holt bring new meaning to the word “suspicious.” Amy and Jake find themselves alone in the file room with the belt and Amy is about to declare herself successful when Jake tells her to take a closer look at the belt.
When she finishes reading “Amy Santiago, will you marry me?” She finds Jake on one knee and holds out a ring to propose to her. It was actually a surprise, which is hard to achieve with an episode lineup that’s already run four times before on the show, and Jake’s decision to propose the heist to Amy is a beautiful testament to the playfulness they bring to each other.