Brooklyn Nine-Nine: 25 Biggest Episodes For Jake & Amys Relationship

The best Jake and Amy episodes of Brooklyn Nine-Nine highlight one of the most popular sitcom couples in recent memory. They seem like polar opposites with Amy being a detail-oriented neat freak, while Jake is more childish in his antics. However, their love proved to be heartwarming and realistic, and their opposite personalities were perfect for one another. 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 all endeared themselves throughout the show’s eight seasons, but there was something about Jake and Amy’s romance that struck a chord with people. From their first kiss to their wedding to having a baby, fans were able to see every major milestone in this romance and they adored every bit of it.

1 “Pilot”

Season 1, Episode 1

Looking back at the key Jake and Amy episodes, viewers have to start at the very beginning with the pilot episode. As with most sitcoms, the pilot was still trying to figure out its tone and characters with a lot of changes to come as the show found its footing. However, it seemed pretty clear that Jake and Amy had a future.

Though he presents it as “the worst date ever,” just the fact that he wants to take her out is enough to plant the seeds of their future relationship from the beginning

The two were presented as rivals, competing with each other to see which of them could make the most arrests. However, Jake’s stipulation for winning the bet is that he gets to take Amy on a date. Though he presents it as “the worst date ever,” just the fact that he wants to take her out is enough to plant the seeds of their future relationship from the beginning. Their chemistry and camaraderie are evident from the start.

2 “The Bet”

Season 1, Episode 13

Jake and Amy’s relationship began blossoming in season 1. At first, it seemed like they couldn’t really stand each other because their personalities were so different, but the clashing techniques certainly made them fun to watch. In the great Brooklyn Nine-Nine episode “The Bet,” things started to change between them. Jake won his competitive bet with Amy, which led to him taking her out on the worst date ever, but Charles pointed out that all of Jake’s efforts were clearly something to do for someone you like, not someone seen solely as 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 Jake was told that they didn’t have to stick around, he opted to stay and spend time bonding with the woman he’d eventually go on to marry.

3 “Operation: Broken Feather”

Season 1, Episode 15

Jake and Amy’s relationship moves 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 sees the two of them realize how much they enjoy each other’s company and working together. In this episode, Amy lets Jake know 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 of them continue to bond was nice, as Jake tried to show her how fun working with him and the Nine-Nine really is, while she seemed confused as to why he cared so much about her staying there and not moving on. When Jake finally realizes he needs to support Amy no matter what she wants, he gives her a letter of recommendation, but she admits she turned it down and wants to remain his partner. It is a sweet moment that shows their growth.

4 “Tactical Village”

Season 1, Episode 19

“Tactical Village” is the episode where Jake realizes that he might like Amy more than just as a partner, and he actually considers asking her out in this episode. It is Charles who notes that there are some sparks between Jake and Amy, which Jake dismisses at first, but he soon realizes that he might be right. He starts to see how much more they have in common and enjoys the attention he receives when they are working together. This leads to him making the first move.

However, when Jake offers to buy everyone drinks, including Amy, she declines the invitation because she admits she has a date with Teddy that evening. Jake just starts babbling about something and chooses to keep his feelings to himself after that. Even after Charles tells Jake that he has to make a move if he wants any chance with Amy, he can’t do it here because Amy said she is going out with Teddy again. This is the Jake and Amy episode where the Teddy relationship begins.

5 “Charges And Specs”

Season 1, Episode 22

The majority of season 1 saw Jake and Amy flirting. In the season finale, “Charges and Specs,” they danced while on a case, but it didn’t seem like much more would come of it. Amy showed a bit of a rebellious side in the episode as she continued to help Jake investigate a subject he was originally told to stay away from. With Holt supporting their investigation, it seemed like they would just be a flirty good team until the next season.

That all changed in the final seconds as Jake was preparing to go deep undercover. He worried about the outcome to the point where he revealed his true feelings for Amy. He hoped something could happen between them, “romantic stylez.” Although they didn’t get together here, it was the first time one of them discussed their feelings for the other.

6 “Undercover”

Season 2, Episode 1

After Jake dropped the bomb on Amy that he would love to be in a romantic relationship with her before leaving for his six-month undercover operation, it left things between them in a tough spot. She had no idea what to say, and he left and was gone for six months. In “Undercover,” Jake comes back to the Nine-Nine, and things are obviously very awkward between the two of them. He finally takes her to have a private conversation, and after a Joe Uterus joke, he admits he left things weird between them.

Amy says she is still with Teddy and nothing will happen between her and Jake.

However, this wasn’t where things would start to move forward. Amy is still dating Teddy, and Jake acts like he is just joking about how he feels, and they move on. Jake does relent later in the episode and tells her that he does really like her, but Amy says she is still with Teddy and nothing will happen between her and Jake. Even with his earlier denial and her outright rejection, the seeds have been planted, and they start to think more about it as the season wears on.

7 “The Jimmy Jab Games”

Season 2, Episode 3

When Jake returned from his undercover operation, things were bound to be awkward between him and Amy. Rosa picked up on it quickly, but Jake was adamant that he had gotten over her. Of course, he was lying to himself and that was clear by the end of the episode. This episode full-on established that Jake and Amy would be the will-they, won’t-they couple of the sitcom.

The employees at the Nine-Nine took part in the Jimmy Jab Games, a series of competitions that took place around the precinct. The competitions include such items as eating expired takeout and racing one another in the bomb suits. Amy seemed to win this iteration of the games fairly, but that wasn’t the case. It’s eventually revealed by Jake that he purposely let Amy win because he actually wasn’t over her.

When Jake reveals this truth to Rosa, she gives him one of her friend’s numbers. That was originally the terms of the bet — that Jake would get the number if he won — but Rosa decided to give it to him anyway in hopes that she could help him move on from Amy.

8 “The Road Trip”

Season 2, Episode 9

In season 2, Amy continued dating Teddy. At the same time, Jake was enthralled with his new girlfriend while Amy started to dislike Teddy because he was boring. While it seemed like Jake was successfully moving on, Amy’s relationship was stagnating, only further fueling the will-they-won’t-they of the pairing. Amy and Jake got assigned on a work trip together and both invited their significant others.

Although Jake stayed with his girlfriend, he was blown away by the thought of Amy having feelings for him, proving his crush wasn’t one-sided.

Amy’s plan to break up with Teddy became public knowledge at a dinner together, and Teddy revealed why he believed it was happening instead of allowing himself and Amy to privately discuss their relationship. He said that Jake confused Amy by saying he liked her, and he felt that Amy liked him back. Although Jake stayed with his girlfriend, he was blown away by the thought of Amy having feelings for him, proving his crush wasn’t one-sided.

9 “Boyle-Linetti Wedding”

Season 2, Episode 17

While a lot of the stress from Jake and Amy’s relationship was over Amy dating Teddy, and Jake realizing he was possibly not going to have a chance with her, things switched a little in the “Boyle-Linetti Wedding” episode. Here, Jake reveals his childhood crush, Jenny Gildenhorn (Jillian Davies), is going to 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 their crush is in the past.

Jake offers Amy a ring, while on his knee, and asks her to go to the wedding with him.

Interestingly, Amy emphasizes here that she is not “madly” in “love” with anyone, which is a moment that gives Jake some pause. She still tells him to go for 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 his knee, and asks 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 punchline when Amy brought over Gina’s great-aunt Susan to dance with him. Jake dances with Susan but shares a small smile with Amy, and more seeds are planted for the future.

10 “Det. Dave Majors”

Season 2, Episode 21

Sometimes, the biggest test that a “will they/won’t they” couple on television can face is the threat of someone else dating one of the characters first. That happened a few times in the early episodes of the series and “Det. Dave Majors” focused on that, with the titular character forming a bond with Amy. Jake failed on several occasions to step up and ask her out beforehand, even after his previous relationship ended.

The true reason this is a standout episode for the couple is that Amy rejected Dave since she didn’t want to date cops, sending Jake on a high, followed by a low when he realized the reason. However, Rosa told him earlier that if Amy tucks her hair behind both ears, it means she likes someone, and the audience gets to see Amy do it after Jake leaves, showing 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 huge 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 spilled the beans that he was planning on asking her out. While on the job, to get close to the perp, they acted as an engaged couple, bringing them close together.

This, naturally, led to a flurry of feelings between them, capped when they kissed to keep up their act. When the case ended, they tried to talk about their feelings, and it led them to their first official kiss, with the previous ones all taking place on cases. This sparked their relationship, and they’d never look back.

While a lot of sitcoms might have got the main pairing together at this point only to break them up again relatively quickly to drag out the conflict, the series didn’t take that route with Jake and Amy. From this point on, most of their conflicts were not about breaking up or staying together, but about conflict within the relationship or 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 in the season 2 finale and the two agree that they want to explore a relationship with each other. While the kiss was the start of their relationship, this episode was where it actually began. At first, they decide to keep things “light and breezy,” They then set three important rules for the relationship: they won’t tell anyone, they won’t create labels, and there will be no sex up front.

Jake and Amy reveal their relationship to the team, and this is the official start to their romance.

This becomes tough when Charles won’t stop shipping the two of them together and keeps asking about it. They tell him nothing is happening, but he claims he already wrote his best man’s speech for their wedding. This episode sees them also breaking another rule when they actually sleep together. By the end of the episode, their new captain dies of a heart attack, Jake and Amy reveal their relationship to the team, and this is the official start to their romance.

13 “The Mattress”

Season 3, Episode 7

Amy had been spending nights at Jake’s apartment and her back was hurting due to his bad mattress, so they went shopping for a new one together. Alas, it led to their first major fight as a couple. Jake refused to buy an expensive mattress, causing friction between them. Ultimately, he related the issue to something Captain Holt told him about his own relationship with Kevin, causing Jake to see that this wasn’t a big deal. He chose to get the new mattress because it was important to the woman he cared for.

Out of context, the episode might sound like a relatively boring outing for a TV couple, but it was both funny and heartfelt, allowing for Jake to grow as a romantic partner. This is the kind of mundane fight in real life that a sitcom can make entertaining.

14 “The Cruise”

Season 3, Episode 13

“The Cruise” depicts a crucial moment in any relationship: when both parties say their first “I love you.” Jake won tickets for a cruise with Amy, but their getaway wasn’t all fun and games, as they ran into Jake’s Brooklyn Nine-Nine nemesis/friend Doug Judy, which turned their trip into one with an assassin. That alone is a great setup for a crime sitcom, but allowing the episode to further develop Jake and Amy’s relationship was a good call by the writers.

The critical moment happened when Jake gave in and went salsa dancing with Amy. Amy was first to say “I love you,” but Jake shut down and replied, “Noice. Smort.” Amy looked upset at his reaction until Jake came to the realization and promptly said “I love you, too.” It was clear in the moment that Jake wasn’t trying to avoid saying the words, just that he was so excited by 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 bit hard for Jake because Amy’s father is a retired cop in the series and a hard character to please. Their meeting proved to be a crucial moment for Jake and Amy, though, since Jake went as far as going full-on “Amy mode” and made his own binder with information about her dad. He studied to better understand Amy’s father, and it was an incredibly sweet gesture.

Jake went above and beyond to get his approval, which didn’t work out well.

Jake was desperate to have Amy’s dad like him, even though Mr. Santiago made it clear he wasn’t happy about them being together. Jake went above and beyond to get his approval, which didn’t work out well, but in the end, Amy’s dad understood that they love each other and that’s what matters most.

16 “The Fugitive”

Season 4, Episode 11 & 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 as a prison bus crashed, letting its inmates escape, and setting up Jake for a manhunt. During this time, Jake and Amy planned to move in together, which is a big milestone for taking their relationship to the next level.

The problem was they couldn’t decide who was moving into whose apartment. That led to a bet which harkened back to their pre-dating days. Both ended up catching the same perp and read him his rights, wanting to win. However, Jake stopped to let Amy finish because her happiness and being with her was more important than some simple bet. Plus, it made more sense to move into her apartment since his wasn’t very nice. The episode provided a fun callback for the audience and more growth for Jake.

17 “Chasing Amy”

Season 4, Episode 18

“Chasing Amy” is a crucial episode for Jake and Amy’s Brooklyn Nine-Nine relationship because it showcases how much he loves her. In a prior episode, Jake discovered that Amy wanted to become a sergeant. He was not thrilled at first, but in this episode, he did everything he could to help Amy pass the exam.

Jake even set up a practice test, but she bailed on it, causing him to use his knowledge of Amy to track her down in impressive fashion, even meeting with one of Amy’s friends to question her. Amy was afraid of what the sergeant position could mean for their relationship. However, Jake reassured her that he always knew she was meant to do more and that she was too good to be afraid of success.

An important part of this episode wasn’t just what Jake did for Amy, but also what Amy did for Jake. Much of the series involves Jake being the one to have to grow, but here, Amy made a concession for him as well.

After he helped her get to the test and understand that their relationship won’t buckle if she was a higher rank than him, Amy decided to gear one of the trivia nights she does with her friends to Jake’s interest instead. It was a way to allow him to have more fun after her friend said he “ruined them”, and thank him for helping her.

18 “HalloVeen”

Season 5, Episode 4

This is one of the many Brooklyn Nine-Nine Halloween Heist episodes. Those episodes are already fan-favorites even without considering any relationship progress in them. As per tradition, the squad took part in the yearly heist competing for the belt and victory. But this episode proved to be so much more than just a competition, as Jake used the heist to propose to Amy.

When Amy found the belt in the evidence room she saw that Jake changed its wording. It read “Amy Santiago, will you marry me?” She happily accepted and this became a massive moment for their relationship embedded in one of the most fun pastimes in the series. Jake also admitted the very moment he realized he wanted to marry Amy, which was so small that it really hammered home just how much he loved her.

19 “Jake & Amy”

Season 5, Episode 22

Amy’s perfectly planned wedding day was anything but perfect in “Jake & Amy.” Not only did her veil end up ruined, but someone called their wedding venue with a bomb threat. Jake, Amy, and Boyle all 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.

Their ruined wedding day didn’t stop them from getting married, though. They were wed outside in front of the precinct with a robot holding the rings. The robot, in fact, was provided by Teddy and the bomb squad, proving that he wouldn’t be an obstacle to Jake and Amy’s relationship, which was a nice touch for the sitcom. Holt officiated things to make it more emotional. The squad got to celebrate their happy union at the bar in one of the show’s most touching moments.

20 “Honeymoon”

Season 6, Episode 1

The next big event for a couple following the wedding is the honeymoon, which was exactly how Brooklyn Nine-Nine’s sixth season opened. Of course, the romantic getaway was never going to go smoothly for Jake and Amy, as it turned out that a depressed Holt had decided to unwind 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 as Melvil Dewey, inventor of the Dewey Decimal System.

There is a lot of fun in seeing Jake and Amy trying to start their romantic life together while also cheering up Holt. But the real highlight of the episode is seeing the different fantasies Jake and Amy play out for each other. Amy dresses up as Bonnie Bedilia, aka Holly Genarro in Die Hard, while Jake dresses as Melvil Dewey, inventor of the Dewey Decimal System. It is a goofy moment that shows just how made for each other these two are, despite how different they are from one another.