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Brooklyn Nine-Nine: The 20 Most Pivotal Episodes in Jake and Amy's Romance

Writer's picture: Joao NsitaJoao Nsita

Brooklyn Nine-Nine : The 20 Most Pivotal Episodes in Jake and Amy's Romance

From playful rivals to soulmates, Jake Peralta and Amy Santiago's relationship in "Brooklyn Nine-Nine" is one of the most beloved aspects of the show. Their journey, filled with humor, heartwarming moments, and genuine growth, captivated audiences for eight seasons. Their dynamic romance was a perfect blend of wit, charm, and emotional depth, making it a standout feature of the series. Let's revisit the 20 most pivotal episodes that shaped their iconic romance, listed in descending order.

Honeymoon" (Season 6, Episode 1)

20. "Honeymoon" (Season 6, Episode 1)


Why it Matters: The aftermath of a wedding is always a significant transition, and for Jake and Amy, it meant navigating married life while hilariously dealing with a depressed Captain Holt on their honeymoon.



Following their wedding, Jake and Amy's honeymoon takes an unexpected turn when they encounter a despondent Holt at the resort. While trying to balance romance and cheering up their captain, the episode's highlight is their playful role-playing, with Amy as Holly Genarro from "Die Hard" and Jake as Melvil Dewey, showcasing their quirky compatibility. This episode sets the tone for their married life, emphasizing the importance of humor and teamwork in their relationship.

Jake & Amy" (Season 5, Episode 22)

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


Why it Matters: What could go wrong on the big day? Everything! But their ability to overcome every obstacle thrown at them shows how deep their love runs.


Amy's meticulously planned wedding faces chaos with a ruined veil and a bomb threat. Investigating the threat with Jake and Boyle, they discover it's linked to Amy's past, with her ex, Teddy, leading the bomb squad. Despite the setbacks, they marry outside the precinct, officiated by Holt, with Teddy's robot delivering the rings, symbolizing his acceptance of their relationship. This episode highlights the couple's resilience and the support they receive from their friends and colleagues.

HalloVeen" (Season 5, Episode 4)

18. "HalloVeen" (Season 5, Episode 4)


Why it Matters: Not only is it the best "Heist" episode, but it showed the lengths Jake would go to when he knew Amy was the one.



In a memorable Halloween Heist, Jake proposes to Amy, solidifying their relationship in the show's most beloved tradition. Amy discovers Jake's alteration to the heist belt, reading "Amy Santiago, will you marry me?" Jake also reveals the exact moment he knew he wanted to marry Amy, a testament to his deep love. This episode showcases Jake's vulnerability and his commitment to Amy, making it a pivotal moment in their relationship.

Chasing Amy" (Season 4, Episode 18)

17. "Chasing Amy" (Season 4, Episode 18)


Why it Matters: Here we see how much Jake loves Amy as he fully supports her career goals even when he is not thrilled at first.


Jake supports Amy's aspirations to become a sergeant, setting up a practice exam for her. Tracking her down when she bails, he reassures her that her success won't threaten their relationship. Amy reciprocates by dedicating a trivia night to Jake's interests, demonstrating her gratitude and understanding of his needs. This episode highlights the couple's mutual support and their ability to balance personal and professional goals.

"The Fugitive" (Season 4, Episodes 11 & 12)

16. "The Fugitive" (Season 4, Episodes 11 & 12)


Why it Matters: The question of moving in together is a big one, and it leads to the revival of an old bet!


As a prison bus crash sets up a manhunt, Jake and Amy plan to move in together, sparking a debate over whose apartment to choose. They revive their old bet, but Jake prioritizes Amy's happiness over winning,

leading them to move into her apartment. This episode showcases the couple's growing commitment to each other and their willingness to compromise.

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

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


Why it Matters: Meeting the parents! Getting approval from a significant other's parents is never easy.

Jake meets Amy's father, a retired cop, and goes to great lengths to impress him, even creating a binder with information about him.


Despite his efforts, Mr. Santiago remains unimpressed, but ultimately acknowledges their love for each other. This episode highlights the importance of family in their relationship and Jake's dedication to winning over Amy's father.

"The Cruise" (Season 3, Episode 13)

14. "The Cruise" (Season 3, Episode 13)


Why it Matters: The big "I love you"! This episode perfectly blends the humor of the series with a major milestone for Jake and Amy.


On a cruise with Amy, Jake encounters Doug Judy, turning their getaway into a mission involving an assassin. During salsa dancing, Amy says "I love you," and Jake initially responds awkwardly before reciprocating, overwhelmed by his feelings. This episode marks a significant emotional milestone in their relationship, showcasing their vulnerability and deepening connection.

"The Mattress" (Season 3, Episode 7)

13. "The Mattress" (Season 3, Episode 7)


Why it Matters: Their first real fight as a couple where they both learn from each other and grow.


Amy's discomfort with Jake's cheap mattress leads to their first major argument. Jake learns from Captain Holt's advice and chooses to buy an expensive mattress for Amy, demonstrating his growth as a partner. This episode highlights the importance of communication and compromise in their relationship.

"New Captain" (Season 3, Episode 1)

12. "New Captain" (Season 3, Episode 1)


Why it Matters: The beginning of their relationship, even if they didn't tell anyone at first!



Following their kiss, Jake and Amy agree to explore a relationship, setting rules to keep it casual. However, Charles's shipping of them and their breaking of the "no sex" rule lead to them revealing their relationship to the team, marking its official start. This episode marks the beginning of their romantic journey, setting the stage for their future together.

Johnny and Dora" (Season 2, Episode 23)

11. "Johnny and Dora" (Season 2, Episode 23)


Why it Matters: The kiss that sealed the deal. The chemistry between Jake and Amy was undeniable at this point.


Assigned to a robbery case, Jake and Amy pose as an engaged couple, leading to a charged dynamic. Their undercover kiss sparks real feelings, culminating in their first official kiss and the beginning of their relationship. This episode is a turning point in their relationship, showcasing the shift from rivalry to romance.




Brooklyn Nine-Nine: The 20 Most Pivotal Episodes in Jake and Amy's Romance




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

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


Why it Matters: The will-they-won't-they trope wouldn't be complete without the threat of someone else!


Amy's connection with Detective Dave Majors tests Jake's feelings for her. Amy rejects Dave because she doesn't want to date cops, and Rosa points out that Amy tucks her hair behind her ears when she likes someone, hinting that she likes Jake. This episode adds tension and intrigue to their relationship, highlighting Jake's insecurities and Amy's growing feelings.

Boyle-Linetti Wedding" (Season 2, Episode 17)

9. "Boyle-Linetti Wedding" (Season 2, Episode 17)


Why it Matters: The signals are mixed between Jake and Amy as she emphasizes she is not in love with Teddy.


At the Boyle-Linetti wedding, Jake's childhood crush is present, making him nervous. Amy emphasizes that she is not in love with Teddy, giving Jake pause. He asks Amy to the wedding and they share a moment where he offers her a ring. This episode showcases the growing tension and unspoken feelings between Jake and Amy.

The Road Trip" (Season 2, Episode 9)

8. "The Road Trip" (Season 2, Episode 9)


Why it Matters: Amy and Jake learn what the other thinks in this pivotal episode that gives us a glimpse into their feelings.



Amy and Jake invite their significant others on a work trip. Teddy reveals that Jake confused Amy by saying he liked her, confirming Jake's one-sided crush might be reciprocated. This episode provides insight into Jake's feelings and Amy's potential reciprocation, adding depth to their relationship.

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

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


Why it Matters: Jake is not over Amy and shows it in a big way!


Jake's return from his undercover operation is awkward, with Rosa noticing the tension between him and Amy. During the Jimmy Jab Games, Jake intentionally lets Amy win, revealing he isn't over her. This episode highlights Jake's lingering feelings for Amy and the unresolved tension between them.

Undercover" (Season 2, Episode 1)

6. "Undercover" (Season 2, Episode 1)


Why it Matters: The bomb Jake dropped on Amy is still lingering in the air and needs to be addressed.


Jake returns from his undercover operation, creating awkwardness with Amy. He admits he left things weird between them, but Amy says she is still with Teddy. Despite this, the seeds of their potential relationship are planted. This episode sets the stage for future developments in their relationship.

Charges and Specs" (Season 1, Episode 22)

5. "Charges and Specs" (Season 1, Episode 22)


Why it Matters: Jake reveals his true feelings for Amy!


In the season finale, Jake reveals his feelings for Amy before going undercover. He hopes something could happen between them, expressing his romantic interest for the first time. This episode is a significant moment in their relationship, laying the groundwork for future interactions.

Tactical Village" (Season 1, Episode 19)

4. "Tactical Village" (Season 1, Episode 19)


Why it Matters: Jake considers asking Amy out!



Jake realizes he likes Amy more than just a partner and considers asking her out. However, Amy reveals she has a date with Teddy, leading Jake to keep his feelings to himself. This episode marks the beginning of Jake's romantic interest in Amy, setting the stage for their future interactions.

"Operation: Broken Feather" (Season 1, Episode 15)

3. "Operation: Broken Feather" (Season 1, Episode 15)


Why it Matters: The two continue to bond as Jake tries to show her how fun working with him is.


Amy considers a position in the Major Crimes Unit, and Jake tries to convince her to stay. He gives her a letter of recommendation, but she admits she turned down the position to remain his partner. This episode highlights the growing bond between Jake and Amy, showcasing their mutual respect and the potential for a deeper connection.

The Bet" (Season 1, Episode 13)

2. "The Bet" (Season 1, Episode 13)


Why it Matters: All of Jake's efforts are for someone you like, not someone seen solely as competition.


Jake wins a bet with Amy, leading to a "worst date ever." Charles points out that Jake's efforts are for someone he likes, not just a competitor. They bond over past dates during a stakeout, showing sparks between them. This episode is a turning point in their relationship, highlighting the shift from rivalry to potential romance.

Pilot" (Season 1, Episode 1)

1. "Pilot" (Season 1, Episode 1)


Why it Matters: The beginning of everything!



The pilot episode introduces Jake and Amy as rivals, competing to make the most arrests. Jake's stipulation for winning the bet is a date with Amy, planting the seeds of their future relationship. This episode sets the stage for their dynamic and the eventual development of their romance.


Frequently Asked Questions (FAQs) About Jake and Amy's Relationship

  1. 1.In what episode do Jake and Amy first kiss?


    Jake and Amy first kiss in Season 2, Episode 23, "Johnny and Dora," while undercover.

  2. 2.When do Jake and Amy officially start dating?


    They officially start dating in Season 3, Episode 1, "New Captain."

  3. 3.In which episode does Jake propose to Amy?


    Jake proposes to Amy in Season 5, Episode 4, "HalloVeen."

  4. 4.When do Jake and Amy get married?


    Jake and Amy get married in Season 5, Episode 22, "Jake & Amy."

  5. 5.What makes Jake and Amy's relationship so appealing to viewers?


    Their relationship is appealing because it evolves from a competitive rivalry to a supportive and loving partnership, filled with humor, genuine affection, and personal growth.

  6. 6.How do Jake and Amy balance their personal and professional lives?


    They navigate their professional and personal lives by respecting each other's ambitions, supporting each other's goals, and finding humor in their shared experiences.

  7. 7.What are some of the challenges Jake and Amy face in their relationship?


    They face challenges such as balancing their different personalities, dealing with career ambitions, and navigating personal insecurities.

  8. 8.Do Jake and Amy have children?


    Yes, in the final season, Jake and Amy have a son named Mac.

  9. 9.How does Captain Holt influence Jake and Amy's relationship?


    Captain Holt serves as a mentor and father figure, offering guidance and wisdom that helps them navigate their relationship and careers.

  10. 10.What is the secret to Jake and Amy's successful relationship in "Brooklyn Nine-Nine"?


    Their success lies in their ability to grow together, support each other's dreams, and maintain a sense of humor and playfulness in their relationship.


    Looking for hilarious sitcom insights and comedy TV recommendations? Dive into these must-read articles from That Love Podcast:

    • The Evolution of George Costanza and Jerry Seinfeld’s Friendship on Seinfeld – A deep dive into the iconic duo’s comedic chemistry and how their dynamic shaped the show. Click here.

    • Jake and Amy: The 20 Most Pivotal Episodes in Their Brooklyn Nine-Nine Romance – Relive the best moments of this fan-favorite couple and their unforgettable journey. Click here.

    • TV Review: XO, Kitty Season 1 – A Charming Spin-Off That Finds Its Own Identity – A fun and fresh take on the To All the Boys universe. Click here.

    • The Top 10 Teen TV Shows on Netflix – From heartfelt dramas to laugh-out-loud comedies, discover the best teen series streaming now. Click here.

    • The Evolution of Howard and Bernadette’s Relationship in The Big Bang Theory – From flirtation to family life, explore their growth as a couple. Click here.

    • The Evolution of Howard and Sheldon’s Relationship in The Big Bang Theory – A closer look at their hilarious rivalry and eventual friendship. Click here.

    • The Evolution of Penny and Sheldon’s Relationship in The Big Bang Theory – Analyzing their unique bond that blended sarcasm and sincerity. Click here.

    • The Evolution of Chandler and Joey’s Friendship on Friends – A look at one of TV’s most beloved bromances. Click here.

    • The Evolution of Phoebe and Joey’s Relationship on Friends – Exploring the quirky and heartwarming connection between these two fan-favorites. Click here.

    • TV Review: Cunk on Life – A Hilarious Journey Through Existence – A satirical and side-splitting take on human history. Click here.

    • The Top 10 Queer TV Shows That Revolutionized Representation on Screen – Celebrating groundbreaking series that reshaped LGBTQ+ storytelling. Click here.

    • The 15 Most Memorable Seinfeld Moments – From Elaine’s Dance Moves to the Puffy Shirt – Revisit the funniest and most iconic Seinfeld scenes. Click here.

    Enjoy exploring these sitcom and comedy TV recommendations!



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