|Season One:||M.E. Time|
|Season Two:||Chocolate Milk|
Ray Holt and Amy Santiago are police colleagues, friends as well as having a mentor/mentee relationship. From the moment Ray Holt is appointed captain of The 99th Precinct, Amy Santiago tries desperately to impress him. She is hoping that he will be the mentor she needs to help her achieve her goal of becoming captain. Unfortunately, more often than not, Amy embarrasses herself in Holt's presence.
- Amy and Holt meet
- Amy and Holt go on a stakeout
- Holt asks Amy to run the Junior police program
- Amy tells Holt why Jake punched Jimmy Brogan after he manipulates her by saying he thought that they were close
- Amy invited Holt to her thanksgiving so she can ask Holt to mentor her
- Amy is annoyed that Holt pays more attention to Jake as he acts
- Holt finds her speech as she doesn't get a chance to say it to him. He has spell checked it and labelled the awkward parts. Amy is happy as he mentored her
- Amy tells Holt that she would have loved to be Holt's bodyguard. Holt tells her that he'll consider her next time
- Holt tries to get Amy to take the puppies but she can't as she's allergic
- Holt denies Amy and Jake more cases as he believes the bet could have a bad fallout
- Holt tells Amy to be kind to Gina when she has had her house is burgled and help her
- Holt invites Amy to his birthday party
- Amy decides to find out about Holt's personal life and house to get to know
- Amy embarrasses herself after her topics (hummus and the microwave) don't go down well
- Amy goes into Holt's bedroom to see what he's been watching but gets caught by Jake
- Amy can't believe that Jake doesn't trust Holt enough to inform him about his investigation of Lucas Wint. She then tells Jake that she appointed Holt executor of her will.
- Amy stands up to Holt and, against his orders, helps Jake convince Holt that Wint is guilty.
- Holt's nemesis, Wuntch comes to the precinct and Amy is upset to see that she might give the precinct a bad review and close it
- Amy stands up to Holt, telling him to be the bigger man so that Wuntch gives them a good review
- Holt encourages Amy to run for union rep
- Holt helps Amy stop smoking through exercise
- Amy makes Holt a gift of all of his highlights: "From Ray to Z"
- Amy discovers a mistake in one of Holt's cases and tells him. He thanks her for the gift of telling him he was wrong and asks her to work the case with him
- Holt and Amy reopen the Brooklyn boiler case
- They find out that the accused died and their trip was for nothing
- Amy gives Holt street meat that makes him sick
- Amy apologises but Holt says that they've bonded
- Holt gets Amy to solve an unsolvable puzzle in exchange for Beyoncé tickets
Season Three Edit
Season Four Edit
Running Gag Edit
Amy Embarrassed In Front Of Holt Edit
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A running gag throughout the series is Amy constantly creating awkward situations between her and Captain Holt. She tries harder than anyone to impress him, however, it usually backfires, leaving her feeling embarrassed.
Santiago: Oh. He didn't tell you.
Holt: Tell me what?
Santiago: Never mind. If Jake didn't tell you, it's not my place.
Holt: I'm disappointed in you, Santiago. I thought you and I were close.
Santiago: I know you're manipulating me, but I love it and I will tell you anything!