Jake and Amy’s best episodes Brooklyn Nine-Nine spotlight one of the most popular comedy couples of recent times. They seem polar opposites, with Amy being a neat freak and detail-oriented, while Jake is more childish in his antics. However, their love proved to be touching and realistic, and their opposing personalities were perfect for each other. Throughout the show, fans saw some major milestones in Jake and Amy’s episodes that helped define their relationship.
THE Brooklyn Nine-Nine cast of characters became beloved throughout the series’ eight seasons, but there was something about Jake and Amy’s romance that touched people. From the first kiss to the wedding and the birth of a baby, fans were able to see all the important milestones of this romance and loved every detail of it.
1
“Pilot”
Season 1, Episode 1
Looking back at Jake and Amy’s main episodes, viewers need to start at the beginning, with the pilot episode. As with most comedies, the pilot was still trying to figure out its tone and characters, with many changes to come as the show finds its feet. However, it seemed pretty clear that Jake and Amy had a future.
Although he presents it as “the worst date ever,” just the fact that he wants to date her is enough to plant the seeds of their future relationship from the start.
The two were presented as rivals, competing with each other to see which one could make the most arrests. However, Jake’s condition to win the bet is that he takes Amy out on a date.. Although he presents it as “the worst date ever,” just the fact that he wants to date her is enough to plant the seeds of their future relationship from the start. Their chemistry and camaraderie are evident from the start.
2
“The Bet”
Season 1, Episode 13
Jake and Amy’s relationship began to blossom in the first season. At first, it seemed like they couldn’t stand each other because their personalities were so different, but the conflicting techniques certainly made them fun to watch. In the big Brooklyn Nine-Nine episode “The Bet”, things began to change between them. Jake won his competitive bet with Amy, which led to him going out with her on the worst date ever, but Charles pointed out that all of Jake’s efforts were clearly something to do for someone you care about, not someone seen as just competition.
However, Jake and Amy’s date was interrupted when they were called to a stakeout. While on the roof, they began to reminisce and bond over past dates, showing sparks. Even when they told Jake they didn’t need to stick around, he chose to stay and spend time bonding with the woman he would eventually marry.
3
“Operation: Broken Feather”
Season 1, Episode 15
Jake and Amy’s relationship progresses slowly as they get to know each other better in the first season of Brooklyn Nine-Nine. This includes the episode “Operation: Broken Feather,” which shows the two realizing how much they enjoy each other’s company and working together. In this episode, Amy tells Jake that she is applying for a position in the Major Crimes Unit, and Jake spends much of the episode trying to convince her to stay.
Seeing the two continue to bond was good, as Jake tried to show her how fun he and Nine-Nine really are to work with, while she seemed confused as to why he cared so much about her staying there and not moving on. When Jake finally realizes that he needs to support Amy no matter what she wants, he gives her a letter of recommendation, but she admits that she turned it down and wants to remain his partner. It’s a sweet moment that shows your growth.
4
“Tactical Village”
Season 1, Episode 19
“Tactical Village” is the episode where Jake realizes he might like Amy more than just as a partner, and he actually considers asking her out in this episode. It’s Charles who notices that there are some sparks between Jake and Amy, which Jake dismisses at first but soon realizes he might be right. He begins to see how much they have in common and enjoys the attention he receives when they work together. This prompts you to take the first step.
However, when Jake offers to buy drinks for everyone, including Amy, she turns him down because she admits she has a date with Teddy that night. Jake starts babbling about something and chooses to keep his feelings to himself after that. Even after Charles tells Jake that he needs to take action if he wants any chance with Amy, he can’t do that here because Amy said she’s going to date Teddy again. This is the Jake and Amy episode where Teddy’s relationship begins.
5
“Rates and specifications”
Season 1, Episode 22
Most of the first season saw Jake and Amy flirting. In the season finale, “Charges and Specs,” they danced while working on a case, but it didn’t seem like much else would happen. Amy showed a bit of a rebellious side in the episode as she continued to help Jake investigate a matter he was originally told to stay away from. With Holt supporting the investigation, it seemed like they would just be a nice flirty team until next season.
Everything changed in the final seconds, when Jake was preparing to disguise himself. He cared about the result to the point where he he revealed his true feelings for Amy. He hoped something might happen between them, “romantic style.” Although they hadn’t gathered here, it was the first time either of them had discussed their feelings for the other.
6
“Disguised”
Season 2, Episode 1
After Jake dropped the bombshell on Amy that he would love to have a romantic relationship with her before he left for his six-month undercover operation, it left things between them in a difficult place. She had no idea what to say and he left for six months. In “Undercover”, Jake returns to Nine-Nine, and things are obviously very awkward between the two.. He finally takes her in for a private talk and, after a joke from Joe Uterus, admits that he made things awkward between them.
Amy says she’s still with Teddy and that nothing will happen between her and Jake.
However, this was not where things would start to move forward. Amy is still dating Teddy, and Jake acts like he’s just joking about how he feels, and they move on. Jake relents later in the episode and tells her he really likes her, but Amy says she’s still with Teddy and nothing will happen between her and Jake. Even with their previous denial and outright rejection of her, the seeds have been planted and they start to think about it more as the season progresses.
7
“The Jimmy Jab Games”
Season 2, Episode 3
When Jake returned from his undercover operation, things would get awkward between him and Amy. Rosa realized this quickly, but Jake was convinced he was over her. Of course, he was lying to himself and that became clear by the end of the episode. This episode fully established that Jake and Amy would be the sitcom’s will-they-won’t-they couple.
Nine-Nine employees participated in the Jimmy Jab Games, a series of competitions that took place around the police station. Competitions include things like eating expired food and competing against each other in bomb suits. Amy seemed to win this iteration of the games fair and square, but that wasn’t the case. It is eventually revealed by Jake that he purposely let Amy win because he didn’t actually get over her.
When Jake reveals this truth to Rosa, she gives him a friend’s number. These were originally the terms of the bet – that Jake would receive the number if he won – but Rosa decided to give it to him anyway, hoping she could help him leave Amy.
8
“The Road Trip”
Season 2, Episode 9
In season 2, Amy continued dating Teddy. At the same time, Jake became enchanted with his new girlfriend while Amy began to dislike Teddy because he was boring. While it seemed like Jake was successfully moving on, Amy’s relationship was stagnant, only further fueling the couple’s will-they-won’t-they. Amy and Jake were assigned to go on a work trip together and they both invited important people.
Although Jake stayed with his girlfriend, he was impressed by the idea of Amy having feelings for him, proving that his passion was not one-sided.
Amy’s plan to break up with Teddy became public knowledge at a dinner together, and Teddy revealed why he believed this was happening rather than allowing him and Amy to privately discuss their relationship. He said that Jake confused Amy by saying he liked her and felt Amy liked him back. Although Jake stayed with his girlfriend, he was impressed by the idea of Amy having feelings for him, proving that his passion was not one-sided.
9
“Boyle-Linetti Wedding”
Season 2, Episode 17
Although much of the stress in Jake and Amy’s relationship was due to Amy dating Teddy, and Jake realizing he possibly wouldn’t have a chance with her, things changed a bit in the episode “Boyle-Linetti Wedding”. Here, Jake reveals that his childhood crush, Jenny Gildenhorn (Jillian Davies), will be at the wedding and he is nervous. Boyle wants Jake to stop talking about Jenny since Amy is there, but Jake says that she is “madly in love” with Teddy and that their crush is in the past.
Jake offers Amy a ring while on one knee and invites her to go to the wedding with him.
Interestingly, Amy emphasizes here that she’s not “madly” in love with anyone, which is a moment that gives Jake pause. She even tells him to go after Jenny since he said their crush is in the past, which sends more mixed signals. Amy and Jake then share a moment where Jake offers Amy a ring, while on one knee, and invites her to go to the wedding with him.
Amy agrees and while there they see Jenny dancing with lots of people, causing Amy to ask Jake if he wants to slow dance with someone else. It was just a tease that led to a fun joke when Amy brought Gina’s great-aunt Susan to dance with him. Jake dances with Susan, but gives Amy a small smile, and more seeds are planted for the future.
10
“Det. Dave Majors”
Season 2, Episode 21
Sometimes, The biggest test a will-they/won’t-they television couple can face is the threat of someone else dating one of the characters first. This happened a few times in the first few episodes of the series and “Det. Dave Majors” focused on this, with the titular character forming a bond with Amy. Jake failed on several occasions to step up and ask her out in advance, even after his previous relationship ended.
The real reason this is a standout episode for the couple is that Amy rejected Dave because she didn’t want to date cops, leaving Jake high, followed by low when he realized why. However, Rosa previously told him that if Amy puts her hair behind her ears, this means she likes someone, and the audience will see Amy do this after Jake leavesshowing that all hope is not lost, even if Jake didn’t know it right away.
11
“Johnny and Dora”
Season 2, Episode 23
This episode is important for Jake and Amy’s relationship from beginning to end. Jake and Amy were assigned a robbery case, but he was initially reluctant to work with her and revealed that he was planning to ask her out. During work, to get closer to the criminal, they acted like an engaged couple, bringing them closer.
This, naturally, led to a wave of feelings between them, culminating when they kissed to continue acting. When the affair ended, they tried to talk about their feelings, which led to their first official kiss, the previous ones all being affairs. This sparked their relationship and they would never look back.
While many sitcoms might have brought the main pair together at this point, only to separate them again relatively quickly and prolong the conflict, the series didn’t go that route with Jake and Amy. From that point on, most conflicts were not about breaking up or staying together, but rather conflict within the relationship or the work itself.
12
“New Captain”
Season 3, Episode 1
Season 3 of Brooklyn Nine-Nine takes Jake and Amy’s relationship in a new direction. This followed their kiss at the end of Season 2 and they both agree that they want to explore a relationship with each other. Although the kiss was the beginning of the relationship, it was in this episode that it really began. At first, they decide to keep things.”light and airy“They then established three important rules for their relationship: they will not tell anyone, they will not create labels and there will be no sex in front of them.
Jake and Amy reveal their relationship with the team, and this is the official beginning of their romance.
This becomes difficult when Charles won’t stop sending the two of them together and keeps asking about it. They say nothing is happening, but he claims he has already written his best man’s speech for the wedding. This episode also shows them breaking another rule when they actually sleep together. At the end of the episode, their new captain dies of a heart attack, Jake and Amy reveal their relationship with the team, and this is the official beginning of their romance.
13
“The Mattress”
Season 3, Episode 7
Amy was spending nights at Jake’s apartment and her back hurt from the bad mattress, so they went shopping for a new one together. Unfortunately, this led to their first big fight as a couple. Jake refused to buy an expensive mattress, causing friction between them. Ultimately, he related the problem to something Captain Holt told him about his own relationship with Kevin, causing Jake to realize that it was no big deal. He chose to buy the new mattress because it was important to the woman he cared for.
Out of context, the episode might seem relatively boring for a TV couple, but it was funny and heartfelt, allowing Jake to grow as a romantic partner. This is the kind of mundane real-life struggle that a comedy can make fun.
14
“The Cruise”
Season 3, Episode 13
“O Cruzeiro” portrays a crucial moment in any relationship: when both parties say the first”I love you.” Jake won tickets to a cruise with Amy, but their getaway wasn’t all fun and games when they found Jake’s house. Brooklyn Nine-Nine enemy/friend Doug Judy, who turned his trip into one with a killer. That alone is a great setup for a crime comedy, but allowing the episode to further develop Jake and Amy’s relationship was a good decision by the writers.
The critical moment came when Jake gave in and went salsa dancing with Amy. Amy was the first to say “I love you”, but Jake hung up and replied: “Noise. Smort.” Amy seemed upset by his reaction until Jake noticed and promptly said “I love you too.” It was clear at that moment that Jake wasn’t trying to avoid saying the words, just that he was very excited about Amy’s admission.
15
“Mr. Santiago”
Season 4, Episode 7
Meeting a significant other’s parents is a big deal. Good impressions need to be made, but it was a little difficult for Jake because Amy’s father is a retired police officer from the series and a difficult character to like. Their meeting proved to be a pivotal moment for Jake and Amy, as Jake went so far as to go into “Amy mode” and made his own folder with information about her father. He studied it to better understand Amy’s father, and it was an incredibly kind gesture.
Jake did everything he could to get her approval, which didn’t work out well.
Jake was desperate for Amy’s father to like him, although Mr. Santiago made it clear that he was not happy about them being together. Jake did everything to get her approval, which didn’t work, but in the end, Amy’s father understood that they loved each other and that’s what matters most.
16
“The Fugitive”
Season 4, episodes 11 and 12
Season 4’s “The Fugitive” was a two-part episode where one of a cop’s worst nightmares came true. But in this case, it was one of Jake’s lifelong dreams when a prison bus crashed, letting its inmates escape and setting Jake up for a manhunt. During that time, Jake and Amy planned to live togetherwhich is a huge milestone in taking their relationship to the next level.
The problem was that they couldn’t decide who would move into whose apartment. This led to a bet that dates back to the days before they dated. They both ended up catching the same criminal and were read his rights, wanting to win. However, Jake stopped to let Amy finish because his happiness and being with her were more important than a simple bet. Besides, it made more sense to move into her apartment since his wasn’t very nice. The episode provided a fun return for the audience and more growth for Jake.
17
“Chasing Amy”
Season 4, Episode 18
“Chasing Amy” is a pivotal episode for Jake and Amy Brooklyn Nine-Nine relationship because it shows how much he loves you. In a previous episode, Jake discovered that Amy wanted to become a sergeant. He wasn’t thrilled at first, but in this episode, he did everything he could to help Amy pass her exam.
Jake even organized a practice test, but she backed out, causing him to impressively use his knowledge of Amy to track her down, even meeting up with one of Amy’s friends to question her. Amy was scared of what the sergeant position might mean for their relationship. However, Jake assured her that he always knew she should do more and that she was too good to be afraid of success.
An important part of this episode was not only what Jake did for Amy, but also what Amy did for Jake. Much of the series involves Jake needing to grow up, but here Amy made a concession for him too.
After he helped her take the test and understand that their relationship wouldn’t fail if she ranked higher than him, Amy decided to organize one of the trivia nights she does with her friends for Jake’s interest. . It was a way to allow him to have more fun after her friend said he “ruined” them, and to thank him for helping her.
18
“HalôVeen”
Season 5, Episode 4
This is one of many Brooklyn Nine-Nine Halloween heist episodes. These episodes are already fan favorites, even without considering any relationship progress in them. As is tradition, the cast participated in the annual assault competing for the belt and victory. But this episode proved to be much more than just a competition, as Jake used the robbery to propose to Amy.
When Amy found the belt in the evidence room, she saw that Jake changed his text. It said “Amy Santiago, will you marry me?” She happily accepted and this became a great moment for their relationship, incorporated into one of the most fun pastimes in the series. Jake also admitted the exact moment he realized he wanted to marry Amy, which was so small that it really made it clear how much he loved her.
19
“Jake and Amy”
Season 5, Episode 22
Amy’s perfectly planned wedding day was anything but perfect on “Jake & Amy.” Not only did her veil end up ruined, but someone called the wedding venue with a bomb threat. Jake, Amy and Boyle investigated the threat on what should have been the happiest day of the couple’s lives. It proved to be someone from Amy’s past and the person in charge of the bomb squad was her ex, Teddy.
Ruined Wedding Day Didn’t Stop Them From Getting Marriedhowever. They got married outside, in front of the police station, with a robot holding the rings. The robot, in fact, was provided by Teddy and the bomb squad, proving that it would not be an obstacle to Jake and Amy’s relationship, which was a nice touch for the show. Holt made things official to make it more emotional. The cast was able to celebrate their happy union at the bar in one of the most emotional moments of the show.
20
“Honeymoon”
Season 6, Episode 1
The next big event for a couple after the wedding is the honeymoon, which was exactly like this Brooklyn Nine-Nine open sixth season. Of course, the romantic getaway was never going to go well for Jake and Amy, as a depressed Holt decided to relax and think about his career prospects at the same resort.
Amy dresses up as Bonnie Bedilia, aka Holly Genarro in Die Hard while Jake dresses up as Melvil Dewey, inventor of the Dewey Decimal System.
It’s really fun to see Jake and Amy trying to start their romantic life together while also cheering Holt up. But the real highlight of the episode is seeing the different fantasies that Jake and Amy play out for each other. Amy dresses up as Bonnie Bedilia, aka Holly Genarro in Die Hardwhile Jake dresses up as Melvil Dewey, inventor of the Dewey Decimal System. It’s a silly moment that shows how made for each other these two are, despite being different from each other.