[tldr_position]When it comes to Brooklyn Nine-Nine, there are a lot of dynamics to admire. One is the number of relationships and couples that take place in the series, including Jake and Amy, which many thought wouldn’t have happened.
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 episodes that helped define their relationship.
Updated on November 2, 2021 by Kevin Pantoja: For new fans to Brooklyn Nine-Nine or even those returning to it, they might have one major question. “When do Jake and Amy get together?” The answer lies in watching through the show to see which episodes are the most important to their relationship. 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.
15 “The Bet” (Season 1, Episode 13)
Jake and Amy’s relationship began blossoming in season 1. At first, they couldn’t really stand each other because their personalities were so different. In “The Bet,” things started to change. Jake won his competitive bet with Amy that led to him taking her out on the worst date ever, but Charles pointed out that all of Jake’s effort was clearly something you do for someone you like.
Their date was interrupted when they were called to a stakeout. While on the roof, they started 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 go on to marry.
14 “Charges And Specs” (Season 1, Episode 22)
The majority of season 1 saw Jake and Amy do a bit of flirting that kept building towards the eventual romance that fans wanted. The season finale, “Charges and Specs,” saw them do a bit of dancing while on a case, but it didn’t seem like much more would come of it.
That all changed in the final seconds. As Jake was preparing to go deep undercover, he worried that something could happen so 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.
13 “The Jimmy Jab Games” (Season 2, Episode 3)
When Jake returned from his undercover operation, things were bound to be a bit awkward between him and Amy. Rosa picked up on it pretty quickly but Jake was adamant that he had gotten over her. Of course, he was mostly just lying to himself and that was clear by the end of the episode.
The employees at the Nine-Nine took part in the Jimmy Jab Games, a series of competitions that took place around the precinct. Amy seemed to win this iteration of the games fairly, only for Jake to reveal that he purposely let her win because he actually wasn’t over her at all and would pursue her again later in the season.
12 “The Road Trip” (Season 2, Episode 9)
In season 2, Amy goes on to date Teddy. Nobody on the team seems to like him, especially Jake. At the same time, Jake was enthralled with his new girlfriend while Amy started to dislike Teddy. 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. 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.
11 “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 dating one of the characters first. “Det. Dave Majors” focused on that, with the titular character forming a bond with Amy as Jake failed on several occasions to step up and ask her out beforehand.
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 and a low. However, Rosa told him earlier that if Amy tucks her hair behind both ears, it means she likes someone, and the audience got to see Amy do it after Jake left, showing all hope was not lost.
10 “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, in order to get close to the perp, they acted as an engaged couple, bringing them close together.
This led to a flurry of feelings, 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 taking place on cases. This sparked their relationship and they’d never look back.
9 “The Mattress” (Season 3, Episode 7)
On paper, the premise of season 3’s “The Mattress” doesn’t seem all that important. 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.
8 “The Cruise” (Season 3, Episode 13)
“The Cruise” depicts any crucial moment for any relationship, which is 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 nemesis/friend Doug Judy, which turned their trip into one having to deal with an assassin.
The critical moment happened at the end 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 until Jake came to the realization and promptly said “I love you, too.”
7 “Mr. Santiago” (Season 4, Episode 7)
Meeting asignificant 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 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.
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.
6 “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, 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 way more important than some simple bet.
5 “Chasing Amy” (Season 4, Episode 18)
“Chasing Amy” is a crucial episode for Jake and Amy’s relationship because it showcased 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.
He 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. 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’s too good to be afraid of success.
4 “HalloVeen” (Season 5, Episode 4)
This is one of the many wild Halloween heist episodes in Brooklyn Nine-Nine. As per tradition, the squad took part in the 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. Jake 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.
3 “Jake & Amy” (Season 5, Episode 22)
It’s no surprise that one of the biggest milestones in Jake and Amy’s relationship was the day they get married. Amy’s perfectly planned day was anything but perfect, though, as someone called the venue with a bomb threat. 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. 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.
2 “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. 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.
1 “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 he 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.
NEXT: 5 Times Jake & Rosa Are Friendship Goals In Brooklyn Nine-Nine (& 5 Times Charles & Amy Are)
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