The Ultimate Timeline of Jake and Amy's Epic Love Story: Unveiling the 18 Most Memorable Brooklyn Nine-Nine Episodes

Summary

The best Jake and Amy episodes of Brooklyn Nine-Nine showcased their heartwarming and realistic love story, despite their opposite personalities.

In the series, fans were able to witness significant stages in Jake and Amy's relationship, including their initial kiss, wedding, and the beginning of a family. These episodes showcased the profound extent of Jake's affection for Amy, as he consistently went the extra mile to encourage her aspirations, ultimately opting to be a stay-at-home father in the final episode.

The best episodes featuring Jake and Amy on Brooklyn Nine-Nine showcase one of the most beloved sitcom couples in recent memory. Despite their contrasting personalities - with Amy being organized and detail-oriented, and Jake being more carefree and playful - their love story is heartwarming and relatable. Throughout the series, viewers witnessed significant moments in Jake and Amy's relationship that helped shape their bond. While all the characters on Brooklyn Nine-Nine were adored by fans, there was something particularly special about Jake and Amy's romance. From their first kiss to their wedding and the arrival of their baby, fans were able to witness and cherish every important milestone in their journey. The connection between Jake and Amy is so strong that attempting to condense their highlights into just ten episodes would not do justice to their relationship.

18 "Pilot" (Season 1, Episode 1)

Looking back, to understand the evolution of Jake and Amy's relationship in key episodes, viewers must start with the pilot episode. Like most sitcoms, the pilot was still in the process of finding its tone and characters, and significant changes would occur as the show gained momentum. However, it was quite evident that Jake and Amy had a future together.

Initially portrayed as rivals, constantly competing to see who could make the most arrests, the bet between Jake and Amy included a condition: if Jake won, he would take Amy on a date with the expectation of intimacy. Jake's behavior, including suggestive comments, diminished his charm in his interactions with Amy, but fortunately, this phase was short-lived. Nevertheless, the foundation of their relationship was established during this time.

17 "The Bet" (Season 1, Episode 13)

Jake and Amy's relationship blossomed in season 1 as they initially found it difficult to tolerate each other due to their contrasting personalities. However, a significant turning point occurred in "The Bet" when Jake emerged triumphant, resulting in taking Amy on the worst date imaginable. Charles astutely recognized that Jake's immense effort was a clear indication of his affection towards her.

Their date was abruptly interrupted by a stakeout call. Despite the interruption, while on the rooftop, they began reminiscing about and connecting over their previous dates, igniting a spark between them. Even though they were given the option to leave, Jake made the deliberate choice to stay and bond further with the woman he would eventually marry.

16 "Charges And Specs" (Season 1, Episode 22)

The majority of season 1 witnessed Jake and Amy engaging in playful flirtation, gradually building up to the desired romance by fans. In the season finale, titled "Charges and Specs," they shared a lighthearted dance during a case, giving little indication of what may transpire between them. However, everything changed in the final moments. As Jake prepared himself for a deep undercover mission, his concerns led him to confess his true emotions to Amy. He expressed a hopeful desire for something to develop between them, in a "romantic stylez" manner. Although they did not become a couple at this point, it marked the first instance where one of them openly spoke about their feelings towards the other.

15 "The Jimmy Jab Games" (Season 2, Episode 3)

Upon Jake's return from his undercover operation, tensions were palpable between him and Amy. Rosa quickly caught onto this, although Jake himself insisted that he had moved on. However, it became evident by the end of the episode that he was simply deceiving himself. Within the confines of the precinct, the employees of Nine-Nine engaged in the Jimmy Jab Games, a series of competitions. While it appeared that Amy had legitimately emerged as the winner of this round, Jake disclosed that he had intentionally allowed her victory, as he could not deny his lingering feelings for her and planned to reignite their connection later in the season.

14 "The Road Trip" (Season 2, Episode 9)

In season 2, Amy begins dating Teddy, but Jake and the rest of the team aren't fond of him. As Amy's relationship progresses, she starts to lose interest in Teddy, while Jake becomes infatuated with his own girlfriend. On a work trip that both Amy and Jake are assigned to, they bring along their significant others. During a dinner together, Amy's plan to end things with Teddy becomes public knowledge, and Teddy explains why he thinks it's happening. He reveals that Jake's feelings for Amy confused her, as he expressed liking her and she seemed to reciprocate those feelings. Even though Jake remains with his girlfriend, he is astonished by the idea that Amy may have feelings for him, showing that his crush was not one-sided.

13 "Det. Dave Majors" (Season 2, Episode 21)

Sometimes, the biggest challenge faced by a television couple in the classic "will they/won't they" scenario is when one of the characters starts dating someone else. This was exactly what happened in the episode titled "Det. Dave Majors," where the main character, Dave, formed a connection with Amy while Jake missed his chances to ask her out. What made this episode truly memorable for the couple was Amy's rejection of Dave due to her aversion to dating cops, leaving Jake on an emotional rollercoaster. However, earlier in the episode, Rosa had informed Jake that if Amy tucks her hair behind both ears, it means she likes someone. As Jake left, the audience witnessed Amy doing exactly that, providing a glimmer of hope amidst the uncertainty.

12 "Johnny And Dora" (Season 2, Episode 23)

Beginning to end, this episode marks a pivotal moment in Jake and Amy's relationship. At first, Jake hesitated to collaborate with Amy on a robbery case, inadvertently revealing his intention to ask her out. However, during the investigation, they cleverly posed as an engaged couple to establish a connection with the suspect, ultimately bringing them closer together.

11 "The Mattress" (Season 3, Episode 7)

This resulted in a rush of emotions, culminating in a staged kiss to maintain their charade. Once the case concluded, they attempted to discuss their feelings, ultimately leading to their inaugural genuine kiss, as all previous instances had been part of their professional endeavors. This ignited their relationship, and from that point onward, they never glanced backwards.

In the third season's episode "The Mattress," a seemingly trivial situation becomes significant. Amy's back starts aching from sleeping on Jake's uncomfortable mattress, prompting them to go shopping for a replacement. However, this innocent task escalates into their first major argument as a couple. Jake's reluctance to purchase a costly mattress fuels conflict between them. Eventually, Jake reflects on a conversation with Captain Holt about his own relationship with Kevin, leading him to realize that this issue is inconsequential. Ultimately, he decides to buy the new mattress as a gesture of love and care for Amy.

10 "The Cruise" (Season 3, Episode 13)

"The Cruise" portrays a pivotal moment in any relationship: when both individuals express their love for each other. Jake unexpectedly wins tickets for a cruise and invites Amy along, but their getaway takes an unexpected turn when they encounter Doug Judy, Jake's nemesis/friend from Brooklyn Nine-Nine. This turns their trip into a challenging situation where they have to confront an assassin. At the climax, Jake reluctantly agrees to go salsa dancing with Amy, leading to the revelation of their true feelings. While Amy is the first to say "I love you," Jake initially deflects with a humorous response of "Noice. Smort." This leaves Amy feeling upset until Jake realizes the significance of the moment and promptly reciprocates by saying, "I love you, too."

9 "Mr. Santiago" (Season 4, Episode 7)

Meeting the parents of your significant other can be quite an important milestone. Ensuring a favorable first impression becomes crucial, especially when faced with the challenge of impressing someone like Amy's father, who happens to be a retired cop known for his difficult-to-please nature. Consequently, Jake understood the significance of this encounter and went above and beyond by adopting the "Amy mode," fashioning his very own binder filled with informative tidbits about Amy's dad.

8 "The Fugitive" (Season 4, Episode 11 & 12)

Jake was determined to win over Amy's father, despite Mr. Santiago's obvious disapproval of their relationship. Going to great lengths, Jake sought his approval, although his efforts proved futile. However, ultimately, Amy's dad came to realize that their love for one another was the most important factor.

"The Fugitive," a two-part episode from Season 4, delves into the horrifying scenario that every cop fears. However, for Jake, it turns out to be a realization of his lifelong aspirations. The chaos unravels when a prison bus collides, leading to the escape of dangerous inmates, and thrusts Jake into a relentless manhunt. Meanwhile, amidst the turmoil, Jake and Amy charted their journey towards shared domesticity, an important milestone that signals the progression of their relationship.

The issue at hand was the inability to determine which person would be relocating to the other's apartment. This predicament resulted in a wager, reminiscent of their pre-dating period. Both individuals ended up apprehending the same culprit and proceeded to inform him of his legal rights, each hoping to emerge victorious. However, Jake graciously paused to allow Amy to conclude the interrogation since her happiness and the time spent together were far more significant than a mere bet.

7 "Chasing Amy" (Season 4, Episode 18)

The "Chasing Amy" episode holds great significance for Jake and Amy's relationship in Brooklyn Nine-Nine as it exemplifies his deep love for her. In a previous episode, Jake learns about Amy's desire to become a sergeant, initially causing mixed emotions. However, in this particular episode, Jake goes above and beyond to support Amy in passing her exam. In a remarkable display of his understanding of Amy, he even orchestrates a practice test, although she decided not to participate. Determined, Jake utilizes his knowledge of Amy to successfully track her down. Amy harbors fears about how the sergeant position may impact their relationship, but Jake reassures her that he has always believed in her potential for greatness and that she should embrace her path to success fearlessly.

6 "HalloVeen" (Season 5, Episode 4)

In this installment of Brooklyn Nine-Nine's Halloween heist episodes, the squad participated in the annual competition for the belt and triumph. However, this particular episode went beyond a simple contest when Jake cleverly used the heist as the stage to propose to Amy.

Upon discovering the belt in the evidence room, Amy was surprised to find that Jake had altered its inscription to read, "Amy Santiago, will you marry me?" Delighted, she joyfully accepted, marking a significant milestone in their relationship. Jake candidly expressed the exact moment he realized his desire to marry Amy, a small yet powerful realization that further emphasized his deep affection for her.

5 "Jake & Amy" (Season 5, Episode 22)

It's not surprising that

4 "Honeymoon" (Season 6, Episode 1)

one of the most significant milestones in Jake and Amy's relationship. However, Amy's meticulously planned day turned out to be far from perfect when the venue received a bomb threat from someone from her past. To further complicate matters, the person in charge of handling the threat turned out to be her ex-partner, Teddy. Despite the chaos and disappointment, Jake and Amy refused to let their wedding day be ruined. Instead, they decided to exchange vows outside in front of the precinct, with a robot serving as the ring bearer. To add an extra touch of sentimentality, Holt, their commanding officer, officiated the ceremony. This unconventional wedding showcased the unwavering love and commitment of Jake and Amy, and it became a heartwarming moment for the entire squad, who later celebrated their joyous union at the bar.

Following their wedding, the next major milestone for any couple is the honeymoon. In the sixth season of Brooklyn Nine-Nine, the show kicks off with this romantic getaway. However, things don't go as planned for Jake and Amy, as they discover that Holt, who is feeling down, has also chosen the same resort to relax and contemplate his career options.

There is a great deal of amusement in witnessing Jake and Amy's endeavor to embark on their romantic journey together, all while trying to uplift Holt's spirits. However, the true highlight of the episode lies in the captivating display of various fantasies that Jake and Amy conjure for one another. Amy dons the guise of Bonnie Bedelia, also known as Holly Genarro from Die Hard, while Jake transforms into Melvil Dewey, the ingenious mind behind the Dewey Decimal System. This lighthearted moment flawlessly exhibits the undeniable compatibility these two share, despite their contrasting personalities.

3 "Casecation" (Season 6, Episode 12)

Jake and Amy, balancing their work and social life, prioritize their first anniversary celebrations, even amidst a stakeout for an ongoing case. However, the blissful discussion about their harmonious marriage is abruptly interrupted as they discover conflicting perspectives about their future as parents. Subsequently, this revelation gives rise to profound inquiries and sets the stage for an exceptionally structured and thoughtful debate.

The episode is a significant one for the couple as they both possess valid reasons for their emotions, yet discover that their dissimilarities might be insurmountable. It is always intriguing to witness flawless television couples confront challenges occasionally. However, the conclusion they arrive at offers a heartwarming promise for their future and enhances the subsequent developments in their relationship even further.

2 "Lights Out" (Season 7, Episode 13)

During season 7, Jake and Amy expanded their family by welcoming a new member. Those particular episodes presented a challenging time for the couple as they spent months grappling with the desire to conceive. Despite their continuous efforts, they faced repeated disappointment. However, when they ultimately succeeded, it became an incredibly significant moment. In the episode "Lights Out," a widespread power outage wreaked havoc in the city. The situation worsened when Amy's water broke, leaving them with no immediate means to reach the hospital. Fortunately, Jake made it to the precinct just in time to assist Amy in delivering their firstborn child, whom they lovingly named Mac.

1 "The Last Day" (Season 8, Episodes 9-10)

In a typical fashion, the final episode of the show evoked strong emotions as it delved into the central romance. Jake devised a plan for one last heist, intending to bid farewell to both Amy and Holt as they ventured into new professional endeavors. However, the twist came when he unexpectedly disclosed that he, too, would be resigning.

Rather than pursuing a different line of work, Jake clarified that his reason for doing so was to embrace the role of a stay-at-home dad for their son. This selfless act highlighted his determination to be the supportive father figure that he never had, all while being a devoted spouse to Amy and her remarkable career. This heartwarming development formed an integral part of the gratifying and touching conclusion to Brooklyn Nine-Nine, laying the foundation for Jake and Amy to live a blissful life together.