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Jake And Amy's Best Moments On Brooklyn Nine-Nine, Ranked

"Brooklyn Nine-Nine" is one of the most adored sitcoms to come out of television in the past decade years. For eight seasons, we watched beloved characters like Terry Jeffords, Gina Linetti, and Captain Holt get themselves and their coworkers in and out of workplace hijinks. Even though that workplace was a police station, it never felt like a forensic procedural and the show often addressed real-world issues. Like most sitcoms, "Brooklyn Nine-Nine" has a core romantic relationship — the one between Jake Peralta and Amy Santiago, who are one of the most underrated on-screen couples ever. 

Despite the fact that Amy is a neurotic, over-achieving rule-follower and Jake is a messy, improvisational goofball, they never seem to clash in a way that feels uncomfortable or unfun to watch. As time goes on and their romantic relationship develops, Amy and Jake help each other overcome their own personal obstacles and become an incredible team. It can be hard to isolate their best moments, but there are definitely standouts throughout the series that illustrate how well they complement each other. Keep reading to find fifteen moments ranked from great to best.

15. Amy proves that she listens to Jake

In the Season 4 episode "The Audit," Amy's old flame Teddy Ramos arrives at the precinct as its auditor. Amy and Jake are immediately mortified. The last time they saw Teddy, Amy awkwardly broke up with him in front of Jake and Jake's then-girlfriend, only for Teddy to point out that the reason Amy wasn't interested in Teddy anymore was because of her feelings for Jake. It was a messy breakup, made worse by the fact that Jake wasn't the only reason Amy wanted to break up with Teddy — mostly, she just thought he was the most boring person she'd ever met.

Jake and Amy are happily dating at this point and Teddy is unsurprised. However, Teddy then tries to prove that he's now more interesting by inviting Jake and Amy to jazz brunch with his new girlfriend. Amy later explains how she used to use to deal with Teddy's boring conversations. Jake worries that this same strategy applies to his own ramblings to Amy but realizes that she has always been listening to him when she points out that she and Jake agree that William Atherton is the second-best "Die Hard" villain. 

Of course, Amy says this after she and Jake have imploded jazz brunch to delete a recording of them talking about Teddy from his phone, but it's the little moments in between the madness that often makes this couple so great to watch.

14. Amy and Jake play dress up

Jake and Amy are very excited to leave the Nine-Nine behind and enjoy their honeymoon in Mexico in the premier episode of Season 6, "Honeymoon," especially after averting a near-disaster at their wedding. Unfortunately, when they arrive, they find that Captain Holt, their boss who was recently passed over for the promotion that was his life's goal, has used the same referral code from Gina to book time at the same Mexican resort. Jake and Amy unselfishly spend a lot of their time trying to cheer up Holt until he decides it is time to return to New York.

Believing that Holt has left, Amy changes into a wig and outfit so that she looks exactly like Bonnie Bedelia's character in "Die Hard," Holly McClane. Jake is overcome with excitement upon seeing her – "Die Hard" is probably Jake's favorite thing in the entire world — but they are forced to set aside their roleplaying to convince Holt not to quit his job. 

At the end of the episode, Holt pays to extend their stay at the resort and Amy puts on her Bonnie Bedelia get-up once again. As an added bonus, Jake has brought his own costume to roleplay as famed librarian Melvil Dewey because nothing turns Amy on more than organization.

13. Jake stands up for Amy against Mrs. Santiago

Season 6's "The Golden Child" focuses on Amy's relationship with her parents and brothers, specifically with her mother and her parents' favorite child, older brother David. Amy's parents rank their children's achievements and keep their photos in specific places throughout the house to reflect those rankings — the least impressive go on the stairs, the more impressive on the piano, and the most impressive, always David, gets their picture on the mantel. This is really messed up, and Amy is excruciatingly envious of her brother, which leads her to spend the episode grappling with that envy as she helps him take down a Brazilian drug cartel.

Throughout the episode, Jake is a wonderful partner. He's there for Amy when she needs support after being set aside for her brother, and also there to remind Amy that she still loves her family despite the fact that their intense competitiveness and judgment are actually low-key horrific. 

His support comes to a head, though, at the end of the episode when he shouts at Amy's mother that she should appreciate her daughter more while Amy is in the bathroom. He also shouts a few other choice feelings that have less to do with Amy — "And another thing! When you say I have an "interesting nose," I know you mean big!" — but it's heartwarming to see how fiercely Jake wants to see Amy appreciated by everyone in her life.

12. Amy advocates for Jake

Jake and Amy were not always a power couple, of course. Audiences watched them flirt for two whole seasons before they decided to date. Still, during that time audiences saw them develop a great friendship and establish enormous respect for each other as colleagues. In the late Season 1 episode "Charges and Specs," Amy helps Jake as he surreptitiously investigates a prominent community figure named Lucas Wint despite having been warned off the case. They work together for most of the episode, but there's one moment, in particular, that shows the development of their relationship. 

When Holt finds out that Jake and Amy have continued to surveil Wint without his permission, he is furious, but Amy interrupts him, her voice shaking with fear. Holt's not necessarily scary, but Amy is devoted to him and has a very difficult time questioning authority figures. "Sir, I am Amy Santiago and I have something to say," she explains that she believes Jake is on to something with his investigation of Wint and that Holt should let Jake pursue the case. Amy never stops sounding terrified as she explains herself to Holt, but it's a huge deal that she spoke up against her idol in Jake's favor. She truly respects him and his investigative skills, and the feeling is mutual. 

11. Amy knows Jake's priorities

Throughout all eight seasons of "Brooklyn Nine-Nine," Amy and Jake often use their professional lives to settle personal disagreements, so it's no surprise when they make a bet over who can catch the most escaped convicts after a prison van break-out in their precinct in the Season 4 episode "The Fugitive." The terms of the bet state that whoever catches the most convicts gets to decide where Jake and Amy will move in together — his place or her place.

In the end, Jake decides to cease his efforts to capture the last convict because he realizes that Amy's apartment is a much better place for two people to live and that he's trying to cling to his apartment for the wrong reasons. This in and of itself is a great moment, but it becomes perfect when Terry complains to Amy that Jake wouldn't stop talking about the Teenage Mutant Ninja Turtles while tracking a convict in the sewers. However, instead of commiserating with Terry as expected, she repeats almost verbatim the very thing Jake said to Terry earlier that day "Come on Terry, we were in a sewer, he's gonst ta think about the turtles."

10. Amy and Jake's 'toit nups'

The Season 5 episode "The Venue" follows Amy and Jake as they spend the day making decisions about their upcoming nuptials as they make their way to drop off the deposit to their dream venue. When they arrive, however, they find that the room has been booked from right under their noses by none other than the Vulture, aka Keith Pembroke from the Major Crimes Unit. 

They take steps to get their venue back, making it all the way to a point where they almost don't tell Keith's fiancée, the shockingly saint-like Jean, that he has been cheating on her just so that he will give release his hold on the venue. Ultimately, they decide to do the right thing and tell Jean that Keith is not a good person, and Keith vows to keep the venue despite the cancellation of his wedding to Jean.

 This episode is less about one particularly great Amy and Jake moment and more about seeing them function as a couple outside of their jobs for a whole episode. It's so fun to see them making decisions about their wedding and not worrying about life or death problems, and we especially love their commitment to throwing "toit nups."

9. Jake and Amy say 'I love you'

The most intimate connection in Jake's life (besides his relationships with Amy and Boyle) is probably the one he shares with his one-time nemesis turned best friend Doug Judy, aka the Pontiac Bandit. There's a special bond between a cop and his arch-enemy, and we're sure Jake would agree. Cut to the Season 3 episode "The Cruise," where Jake and Amy find themselves on a complimentary cruise — their first vacation as a couple. 

They soon realize that they've been drawn there by Doug Judy, who believes that someone is trying to kill him and needs protection. At this point, Jake is still very frustrated by Doug's antics, but he and Amy help him find the assailant and Doug makes a quick escape before they can bring him back to New York to face his criminal charges.

Even though Amy offers to keep the rest of their cruise relaxed, Jake remembers how important her activity itinerary is to her and asks her to salsa dance with him. It is during this funny salsa dancing class (intended for recently widowed elderly people) that Amy first confesses her love to Jake, who says it right back after an initially awkward response — "toit."

8. Jake and Amy, Johnny and Dora

By the time the late Season 2 episode "Johnny and Dora" rolls around, Amy and Jake are in a strange place. They have both admitted romantic feelings to each other at one time or another, and they have both also inadvertently squashed the other's attempt to start something. As they are investigating a career criminal, Amy and Jake go undercover in a restaurant as a newly engaged couple named Johnny and Dora to trick the hostess into making room for them despite their lack of reservation. They find themselves seated next to their target, whose own date is delighted to hear about their relationship and proposal. 

Initially, Jake and Amy are uncomfortable with their cover. However, when the woman next to them asks how they knew they loved each other, Johnny and Dora seem to suddenly become Jake and Amy again as they realize that they're speaking the truth. "He makes me laugh," Amy says. "You know, there's really no one else's opinion who I care about more than hers," says Jake. Needless to say, they decide to date for real by the end of the episode.

7. Amy and Jake have a big conversation

Many of Jake and Amy's best moments as a couple also count as (or lead to) their best moments as individual characters as well. In the Season 6 episode "Casecation," Jake and Amy begin the night with a spontaneous anniversary celebration at the hospital as they wait for a witness to come out of his coma. However, before they can really enjoy themselves, they encounter a huge roadblock to the future of their relationship — and keep in mind, at this point, they've already gotten married. It turns out Jake isn't sure that he ever wants to have kids, and Amy is certain she does. 

Despite the fact that Amy then tries to translate this very complicated relationship issue into an adjudicated debate, this is a serious and potentially devastating moment for the two of them. Jake is scared of becoming a father because his own father was such a mess, and Amy is scared that she will need to end their relationship to start over and have kids with someone else. 

After Jake foils a plot to blow up the witness's hospital room, he tells Amy that he wants to be a father because being scared doesn't mean he'll be a bad father, only that he'll care enough to be a good one. Cue sighs of relief!

6. Jake can't be Amy's handler

At the end of Season 3 of "Brooklyn Nine-Nine," the whole squad is working together to take down notorious gangster Jimmy Figgis so that their friend, detective Adrian Pimento, can return to his life without fear of being killed. In "Maximum Security," Amy goes undercover at a woman's prison in Texas where Jimmy's sister, Maura, is currently incarcerated. Amy's job is to get close to Maura and see if she can get any information about an agent in the FBI on Figgis' payroll. 

Jake and Charles go to Texas with Amy as her handlers and pretend to pull her and her fake baby bump for doctor's appointments whenever she seems to be in danger. Jake pulls Amy so often that she starts to think he doesn't believe she is capable of the task before her, but Jake confesses that he is the one who can't do his job. He can't bear to watch the woman he loves in such a dangerous situation and must therefore leave Texas and refrain from working as her handler. It's a small moment, but one that remains important because it's the first time that Jake and Amy really acknowledge the effect their personal relationship has on their professional lives.

5. Someone wins the bet

Most of the tension between Jake and Amy at the beginning of Season 1 stems from a bet they made before Captain Holt took over the precinct. Amy and Jake often clash in Season 1 because of their opposite approaches to problem-solving and work, with things coming to a head when they decide to see who can charge more felony crimes over the next few months. If Amy wins, Jake has to give her his car, but if Jake wins, Amy has to go on a date with him — not a romantic date, that is, a joke date, which Jake sees as an opportunity to make Amy miserable for an entire evening.

All of this takes place during the Season 1 episode "The Bet," where Jake brings in arrests from a sting operation and wins, proposing the date to Amy with a plastic ring. She reluctantly accepts, and Jake gets some great torture in at the beginning of the night, forcing her to wear a polyester prom dress and dance the steerage jig from "Titanic." However, when Holt asks them to take on a stakeout, Jake stops his antics. Once they are truly just hanging out, Jake realizes that he actually likes her quite a bit. It's a wonderful moment in that is Melissa Fumero's (the actress who plays Amy) favorite scene between Amy and Jake.

4. Jake supports Amy through a tough case

In the Season 6 episode "He Said, She Said," Amy and Jake work on a case involving workplace sexual harassment. Initially, they are called to investigate the assault of a stockbroker, only to find out from the assaulter that she was acting in self-defense and he had been attempting to sexually assault her before she immobilized him. The case is triggering for Amy. She confides in Jake that she was closely mentored by an older male officer at her prior precinct. When she made detective, he took her to dinner and demanded that he get something — something sexual — in return for all of his support. Amy transferred precincts right away, but the trauma of that experience, and the trauma of living every day as a woman in America, have stayed with her.

Jake is a wonderful partner to Amy throughout their time working on the case. Of course, he is supportive and comforting, but most importantly, he listens to Amy and immediately accepts her explanation about how their lives are different because of their genders. When Rosa greets them after a tough moment in their case, Jake explains that "Amy's just upset because the historically entrenched patriarchy has created a culture of victim-shaming that suppresses any power shift in our masculine phallic system." When Rosa and Amy react with shock, he says he watched a documentary about feminism the prior evening because he couldn't sleep. 

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

3. The Halloween Heist proposal

Probably the best-known and most beloved running gag on "Brooklyn Nine-Nine," the Halloween Heist gets progressively more outrageous every season. First Jake wins, followed by Holt in Season 2, then Amy sneaks around and steals the whole thing in Season 3, opening up the field for every member of the Nine-Nine. After Gina's non-detective win in Season 4, Amy, Holt, and Jake are all dead-set on winning Season 5's Heist in "HalloVeen," in which they must 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 look at the belt a little more closely. 

When she's finished reading "Amy Santiago, will you marry me?" she finds Jake on one knee, holding out a ring to propose to her. It was actually a surprise, which is hard to do with an episode set-up that's already been run on the show four times prior, and Jake's decision to propose to Amy with the heist is a beautiful testament to the playfulness that they bring out in each other.

2. Your butt is the bomb

Of course, a list of Amy and Jake's best moments would be incomplete without an acknowledgment of their most traditionally romantic scene — their wedding vows. In the Season 5 episode "Jake & Amy," they are excited to celebrate their wedding only to find out that a bomb threat has been called into their venue, which is a local recreation center after their debacle with the Vulture. To make matters worse, Rosa loses the veil, Amy's ex-boyfriend Teddy is the person assigned to search for the bomb, and Jake's Nakatomi Plaza wedding cake is going to melt.

Of course, everything comes together. Rosa finds the veil, Teddy finds the bomb (which Jake and Amy were convinced didn't exist), and even though they can't get married at the rec center, Amy and Jake arrange to say "I do" on the street right outside the precinct with the help of their friends and coworkers. The whole thing is beautiful, but the episode's best moment is when Amy concludes her vows by saying, "but I do have some bad news. There is a bomb at this wedding as well." She pauses to enjoy the confusion on Jake's face before finishing, "Your butt. Your butt is the bomb. There will be no survivors."

1. Amy's inevitable success

It's difficult to rank any Jake and Amy moment above their wedding ceremony, but the Season 4 episode "Chasing Amy" is the actual crown jewel of their on-screen relationship. To help Amy overcome the enormous stress she's experiencing thanks to her preparation for the NYPD sergeant's exam, Jake arranges a perfect practice test, complete with a room full of mouth breathers, snackers, as well as Hitchcock and Scully, as Amy needs testing conditions that are not pristine. He comes back a few hours later to find that Amy has disappeared.

It's lovely to watch Jake search for Amy because he knows her better than anyone else. He goes through the steps she most likely went through herself and eventually finds her on the roof where they had their stake out together back in Season 1. Jake and Amy's relationship is so successfully depicted because it makes such critical use of their on-screen history without avoiding uncharted territory. 

It turns out that Amy went to that old roof where they first started to feel for each other because she was scared that passing the sergeant's exam will mean that her relationship with Jake will be different — maybe even jeopardized. Jake holds her hands and smiles, saying, "Ames, I've always known you were gonna be my boss." He knows that she's going to accomplish great things, and he's not going to stop loving her for being who she is — someone who will achieve incredible success.