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.
After Captain Holt announces to everyone that he is their new boss, Amy shouts out "Speech!" only to have him tell her that his introduction was his speech. Embarrassed, Amy slouches back into her chair and says, "Short and sweet."
Holt congratulates Amy on her successful drug bust to which Amy responds, "That's why we do this, sir." When Holt asks her if she does it for praise, she is left with no response.
Holt asks if Amy could head up a community outreach. Amy agrees and starts rambling about not only heading it up but she will "head and shoulders" it up. Holt then tells her to be more articulate in front of the children. Adding to her rambling, she replies with, "Yes, sir, I will make better mouth." She looks like she's mentally scolding herself before walking out of Holt's office.
Holt reminds everyone about their paperwork during a morning briefing. Amy tells him she already finished all of hers and Holt tells her that his reminder wasn't for her then. Jake teases her by saying it looked like Holt hates Amy more than he hates him. Holt reprimands her when he hears her talking. Jake teases her again and she responds, resulting in Holt calling her attention once more.
Amy approaches Holt looking at a framed picture of him and she says that he looks amazing. He tells her he hates it and she hurriedly responds a "me too".
After asking Holt on how he wants her to proceed with her case, he says she should figure it out since it's her case. Taken aback by his response, she thanks him and proceeds to bow. She walks away after she tells him she isn't bowing and it's how she walks.
Amy figures out why Holt isn't in the mood and points it out to him that there is nothing he should be worried about. She then tells him how they're birds of a same feather, Holt dismisses her by saying he hates clichés.
Holt tells Rosa and Amy to finish up their paperwork. Amy then replies that Holt's wish is her command, Holt corrects her that it is actually a command. Amy tells him that Holt still has all three wishes then Rosa tells her that she isn't a genie. With nothing else to say, she just announces that they're leaving.
Amy is seen wanting to enter Captain Holt's office which leads to getting Holt's attention. He asks, "Can I help you, Santiago?" to which she responds saying she didn't expect to see Holt there. Then he asks again, "In my office?" With a lack of response, she quickly changes the subject and reminds Holt about her Thanksgiving party.
When Holt arrives in her apartment, he mentions how easy it was to locate it and after she thanks him, she then tells him he looks beautiful. Adding to her embarrassment, Jake congratulates them for having the weirdest conversation ever. (In a later scene with Jake, Holt points out it was odd that Amy called him beautiful.)
Amy approaches Holt in the precinct and opens with, "I think you're... Like, when I was a little girl." Holt asks if Amy thinks he's like when she was a little girl. Amy gives up and start to walk away but Holt stops her and says he's read her toast. After complimenting her, Holt then mentions how Amy can improve her speech, and tells her he marked them with "awk" for awkward. (While Rosa teases her about it, Amy considers it as Holt starting to mentor her.)
It didn't come to his attention up until Jake mentioned Amy wanted to give him a gift but Amy had about 6 gifts she wanted to give to Holt although he insisted that no one should give him any presents.
Amy talks to Holt about him choosing Jake. Holt tells her that the next time someone threatens him, he'll go to Amy. In response, Amy says she can't wait. Realizing it sounded wrong, she starts explaining and Holt just puts on his glasses while looking at her.
When the squad arrives at Holt's house, Amy says to Holt, "Those slacks are a knockout." Upon realizing what she just said, she mutters, "Come on, Amy." (4:22)
After Amy does some recon in the captain's kitchen, she tries to start a conversation about the similarities she found. It turns out Holt had no specific input on her questions and then he promptly excuses himself (15:26)
While Kevin and Holt argues in their bedroom, Jake, Amy, and Terry are stuck inside their bathroom with a dog which Amy is allergic to. Holt hears her sneezing and finds them inside the bathroom. (17:49)