Brooklyn Nine-Nine: 20 Biggest Episodes For Jake & Amys Relationship

Summary

• Jake and Amy’s chemistry sparked from the beginning, with their first date setting the stage for their future relationship.
• The episode “The Bet” marked a turning point in Jake and Amy’s relationship, showing signs of budding romance.
• From their first official kiss in “Johnny and Dora” to eventually becoming parents in “Lights Out,” Jake and Amy’s love story evolved beautifully.

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 neat freak and a bit detail-oriented, 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 milestone Jake and Amy episodes on Brooklyn Nine-Nine 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 the Jake and Amy romance that struck a chord with people. From Jake and Amy’s 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. Jake and Amy are such a great couple that confining their highlights to a mere ten episodes is a disservice to the couple.

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.

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 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 is 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 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.

Their 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 “Charges And Specs”

Season 1, Episode 22

The majority of season 1 saw Jake and Amy flirting. The season finale, “Charges and Specs,” saw them dancing 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 what might happen 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.

4 “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 made it clear that the two would likely 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 can help him move on from Amy.

5 “The Road Trip”

Season 2, Episode 9

In season 2, Amy went on to date 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.

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.

6 “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.

7 “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 head that route with Jake and Amy. From this point on, most of their conflicts were not about breaking up or staying together, but conflict within the relationship or work itself.

8 “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 couple in television, 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.

9 “The Cruise”

Season 3, Episode 13

“The Cruise” depicts any 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.

10 “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 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.

11 “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.

12 “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.

13 “HalloVeen”

Season 5, Episode 4

This is one of the many Brooklyn Nine-Nine Halloween heist episodes in Brooklyn Nine-Nine. 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.

14 “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.

15 “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.

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.

16 “He Said, She Said”

Season 6, Episode 8

…it used a storyline inspired by the Me Too Movement to also demonstrate the strengths in Amy and Jake’s relationship.

It’s not often that sitcoms delve into the darker side of real-world events. Brooklyn Nine-Nine, however, did just that in a handful of episodes, some of which didn’t land well with audiences. “He Said, She Said,” landed better than most of the show’s attempts, largely because it used a storyline inspired by the Me Too Movement to also demonstrate the strengths in Amy and Jake’s relationship. (It also helped that the episode had a great B-plot with Holt going after an escaped murderer he put away years earlier.)

In the episode, Jake was assigned to investigate a possible instance of sexual assault at a company. Amy volunteered to assist since she was weeks ahead on her paperwork. What they found was that the woman who accused a coworker of assault was considering taking a multi-million dollar settlement to stay quiet. That reveal prompted a reveal from Amy – that a mentor tried to kiss her when she made detective because he was “owed it,” leading to her transfer after her denial of him. She never told anyone.

The incident meant the case meant a lot to Amy, and it also meant that Jake understood what he was seeing on the surface could be wrong. He and Amy worked together and uncovered more at the business, leading to another person coming forward. While the case itself didn’t have the outcome the couple might have wanted, it brought them closer together as Amy trusted Jake even more with her secrets.

17 “Casecation”

Season 6, Episode 12

With work cutting into their social life, Jake and Amy make plans to spend their first anniversary together even while staking out a case. Their conversation about their happy marriage suddenly hit a roadblock as they find that they have different opinions on whether or not they should have children. This resulted in some big questions and a well-organized debate.

The episode is a big one for the couple as they each have their own valid reasons for feeling the way they do, but find that their differences may be too much to get past. It is always interesting to see perfect television couples deal with struggles at times. However, the decision that was reached at the end is a sweet promise for their future and makes the later developments in their relationship even better.

18 “Trying”

Season 7, Episode 6

“Trying” covered a lot more time than the usual episode of the sitcom. It spanned more than six months as it recounted several different plots for the characters in the show. The main plot for Jake and Amy, however, was the two of them trying to get pregnant.

The struggle to have a child is a fairly common one in television shows that feature a married couple because multiple episodes typically allow for a longer story. Amy and Jake’s struggle, however, is condensed into mostly this single episode as one of many plots. That actually worked in the show’s favor because it’s a more emotional storyline and the series is very firmly a comedy with the occasional sad or dark moments.

Though Amy and Jake tried numerous things, and nothing worked, they ultimately decided to let things unfold how they may. That’s not how Amy would typically approach a setback, but here, it made sense. It allowed Amy and Jake to breathe and enjoy their relationship before they ended up having a child not long after.

19 “Lights Out”

Season 7, Episode 13

In season 7, Jake and Amy became a family of three. Things were rough in those episodes for the couple as they spent months trying to get pregnant. They struggled and no matter what they tried, it just wasn’t happening. When it finally did, it was a tremendous moment. In “Lights Out,” the city lost power, causing havoc. With Holt and Terry trapped in an elevator, it fell to Amy to enact blackout protocols just as she was preparing to take her maternity leave.

It only got worse when Amy’s water broke, and she had no way of getting to the hospital. Jake reached the precinct in time to help Amy deliver their first child, whom they named Mac, after Die Hard’s John McClane. While it’s very sweet to see all of the hoops that Jake had to go to in order to get to Amy before the baby was born, one of the best aspects of the episode is how united the entire team was in helping Amy through the birth and getting Jake to her.

Rosa stayed by Amy’s side despite her own problems with childbirth, Holt and Terry distracted her with a dance, and Scully and Hitchcock got her a bed to have the baby on. Boyle even called in a favor from the police horse he considered his nemesis to make sure Jake could get there in time. The entire team came together for Jake and Amy’s child.

20 “The Last Day”

Season 8, Episodes 9-10

As is often the case, a show’s series finale proved to be an emotionally gripping episode for its core romance. Jake planned one final heist with Amy as a way to say goodbye to her and Holt as they embarked on new jobs. However, he then shockingly revealed that Jake was also quitting his job.

Instead of going into a new career, Jake explained that he was doing this to become a stay-at-home dad with their son. It was a heartwarming act for Jake to do as he was determined to be the good father that his own dad wasn’t, while also being a supportive husband for his wife’s extraordinary career. It is part of the satisfying and heart-warming Brooklyn Nine-Nine ending and sets up Jake and Amy to live a happy life together.