The key episodes featuring Jake and Amy's progression from colleagues to boyfriend and girlfriend, husband and wife, and now parents.
The Bet
Season 1, Episode 13 - Aired January 14 2014
When Jake wins a bet against Amy over who can catch the most criminals, she must go on a date with him. Meanwhile, Captain Holt holds a celebration for Charles, whose pain meds cause him to be unusually candid.
Charges and Specs
Season 1, Episode 22 - Aired March 25 2014
When Jake continues to investigate a case after it was closed by Commissioner Podolski, he is fired from the NYPD. Meanwhile, Charles is distraught when Vivian breaks up with him right before their wedding.
Undercover
Season 2, Episode 1 - Aired September 28 2014
When Jake finishes his undercover FBI operation and returns to the Nine-Nine, he learns that one of the mobsters got away. Jake returns undercover with the help of Charles.
Meanwhile, the squad creaks under the pressure when Holt tests them with repeated practice drills, without telling them why.
Det. Dave Majors
Season 2, Episode 21 - Aired May 3 2015
When Jake and Amy are assigned to work a case with the best detective in the NYPD, Detective Dave Majors, they both try impress him. Jake is forced to confront his own feelings for Amy when Majors declares his intention to ask Amy out on a date when the case is over.
Meanwhile, when Terry considers taking a job at a private security firm, Gina and Boyle try convince him to stay at the Nine-Nine.
Johnny and Dora
Season 2, Episode 23 - Aired May 17 2015
Captain Holt pairs Jake and Amy up to catch a notorious identity thief. Things take an intimate turn when Jake and Amy go undercover as Johnny and Dora, a newly engaged couple. Meanwhile, the whole precinct is shocked by the news that somebody is leaving the Nine-Nine.
New Captain
Season 3, Episode 1 - Aired September 27 2015
With Captain Holt transferred to the NYPD PR department, the squad struggles to adjust to life under their new captain. Meanwhile, Jake and Amy confront their new relationship state after their first real kiss.
The Mattress
Season 3, Episode 7 - Aired November 15 2015
Jake and Amy convince the Captain to let them work a case together involving a new street drug, but their new relationship gets in the way. Meanwhile, at the precinct, Charles panics when he realizes he's damaged one of Holt's prized possessions and Terry teaches Rosa a lesson in discipline.
The Cruise
Season 3, Episode 13 - Aired January 26 2016
Jake and Amy are excited to go on their first real vacation together, but Amy's perfectly planned cruise ship itinerary is thwarted when they discover an old adversary is on board with them. Meanwhile, Gina and Terry help Captain Holt survive a visit from his sister, Debbie, and Charles and Rosa vie for the same apartment.
Karen Peralta
Season 3, Episode 14 - Aired February 2 2016
On his birthday, Jake brings Amy to meet his mother, but a surprise appearance by his dad throws a wrench in his special day. Meanwhile, Rosa and Charles struggle with a new mandate regarding body cams while on a stakeout with Terry, and Gina forgets to inform the precinct about an important plan of Holt's.
Mr. Santiago
Season 4, Episode 7 - Aired November 22 2016
At Amy's intricately planned Thanksgiving dinner, Jake goes "full Santiago" (binder and all) in order to impress her father (guest star Jimmy Smits), a former cop. With Jake and Amy's focus elsewhere, Charles is left on turkey duty and Holt helps Pimento cope after learning he can no longer work for the NYPD.
HalloVeen
Season 5, Episode 4 - Aired October 17 2017
The Nine-Nine embarks on its fifth annual Halloween Heist and, as usual, everybody has a plan and no one is safe. Relationships and friendships are tested as the title "Amazing Human Slash Genius" must be snagged by midnight, leaving everyone pitted against each other.
The Venue
Season 5, Episode 6 - Aired November 14 2017
The always unwelcome Vulture pops back into Jake and Amy's lives, threatening to swoop in and take something important away from them. Meanwhile, Boyle and Rosa must track down "Sergeant Peanut Butter," the kidnapped NYPD horse that Charles envies, and Holt challenges Terry to be less image-conscious.
Jake & Amy
Season 5, Episode 22 - Aired May 20 2018
Jake and Amy's wedding day is majorly threatened, and Charles and the whole squad rush to help save it. Amidst the chaos, Holt hesitates to open the email that will indicate if he has won his campaign for Commissioner, despite Gina's encouragement. Meanwhile, Terry gently pushes Rosa towards a potential love interest.
Casecation
Season 6, Episode 12 - Aired April 11 2019
Work is so busy for Jake and Amy that they end up celebrating their anniversary while standing guard over a comatose patient in the hospital.
Ding Dong
Season 7, Episode 7 - Aired March 12 2020
Captain Holt deals with a personal loss. Jake must decide whether to take Terry or Charles to an exclusive event.
Lights Out
Season 7, Episode 13 - Aired April 23 2020
The squad investigates when a massive blackout hits Brooklyn.