A reoccuring running gag in the show where Charles is shown to be obsessed with Jake Peralta and Amy Santiago’s relationship.
Season One[]
The Bet[]
- After Charles realises Jake had spent $1,400 on the 'Worst date ever' for Amy and himself, he questions him about why he spent that much. 'Somewhere down deep, you like Amy, like, "like her", like her. Jake refuses after Boyle tells him to sit down and have a proper conversation with her. He says he is not taking advice from him as he lives in his ex-wife's boyfriend's basement.
Tactical Village[]
- After Jake tries to impress Amy with a sexy voice, Charles notes that there are some serious sparks happening between the two of them. Jake denies this.
- Amy and Rosa discuss Amy's past relationship with Teddy, and Jake wonders aloud to Charles what's so great about him. Charles alerts Jake that he sounds jealous.
- Later, Jake asks Charles what he thinks Amy sees in Teddy, and Charles suggests (hint hint) that Jake should try asking her out.
Season Two[]
Johnny and Dora[]
- After Jake and Amy went undercover, Charles asks them how the restaurant (that they were at) was. Amy responds oddly so Charles asks her about why she's acting weird. Jake then admits that Amy and him kissed. Charles is shocked and wants to be told everything but Jake tries to play it off as just a kiss.
Season Three[]
New Captain[]
- Charles finds out that Jake is planning a date with someone. Unaware that Amy is the one Jake is planning the date with, Charles gushes that Jake and Amy should be together. Jake tells him not to put pressure on them, to which Charles reveals he's already written his best man speech for their wedding.
- When the new Captain, Seth Dozerman, dies of a heart attack, Jake ends up admitting that he and Amy were "snorking" in the evidence room. Charles said he's over the moon about this.
The Funeral[]
- Amy tries to talk the squad about a plan to get rid of The Vulture as the Precinct's Captain, that she and Jake was discussing about the night before, but Charles interrupts to get some personal details.
Amy: Jake and I were talking last night.
Charles: Pillow talk alert! Set the scene. Spooning or face-to-face?
Amy: Charles.
Charles: *Mouths* Spooning.
The Mattress[]
- Charles overhears that Jake and Amy are going on their first case together as a couple and expresses his exuberance beyond necessary.
Charles: Hey, guys. I just discovered a new drug too. It's called "your relationship," and I'm high on it.
Jake: Charles, I'm gonna need you to back off, man.
Charles: Roger that.
Jake: Yeah.
Season Four[]
Captain Latvia[]
- Charles apologizes to Jake for saying he will never be a father. Charles continues on by telling Jake that he can make it happen if he just goes to Amy later, and then suggests an after-sex position to Jake.
Charles: I'm sorry I said you'll never be a dad. You will be, and you can make it happen tonight. Just go to Amy and make sure afterwards that she holds her knees to her chest for at least -
Moo Moo[]
- Jake and Amy help babysit Cagney and Lacey. Charles repeatedly talks about the two of them having kids.
Charles: I'm smiling at mommy and daddy. Picking up Cagney and Lacey - one taste of practice parenting, and you two will be so hot to have sex. The Kind that make babies. Amy: Walk away Charles. Charles: Okay, but I'll be back in nine month
Terry: You two think you can handle watching the kids while I meet with Officer Maldack? Charles: Oh they can handle it.
Charles: And while you're talking to him, Jake and Amy can babysit your kids - unless they're to busy making babies of their own. Shaka-daka-dow.
Season Five[]
HalloVeen[]
- When Jake proposes to Amy, Charles becomes overwhelmed by excitement and passes out on the floor.
NutriBoom[]
- Charles becomes invested in getting Jake's money back from NutriBoom only when he realizes the money is for Jake and Amy's honeymoon.
Bachelor/ette Party[]
- Charles plans Jake's Bachelor party. When going over what is going to happen, he says to Jake Peralta that this bachelor party has been 10 years in the making. Jake replies, "I only met Amy 8 years ago." Charles is obsessed with Jake Peralta and his relationships that he had been planning Jake's possible bachelor parties for a long time.
Jake & Amy[]
- Charles had put an engagement announcement in the newspaper about Jake and Amy's upcoming wedding date and place. And when blamed for it, he tells Amy to tread lightly because if she is saying that he somehow ruined Jake's wedding, he will kill himself, its a little weird but, its cute at the same time.
- Jake and Amy's wedding cake arrives on time but has to stay outside of the venue due to the bomb threat. Charles said he will keep it chilled with his cool breath. He's blowing on it when Jake sees this and asks Charles why he's spitting on the cake. Charles responds, "Because I didn't ruin your wedding."
- When Jake and Amy decides to just get married at City Hall instead, Charles interrupts saying he was eavesdropping and is always eavesdropping. He also said:
"Look, I didn't spend the last seven years watching your love ripen, only to have it sullied by a city hall wedding. You're getting married right here, right now."
- Charles ends up deciding himself that he will set up Jake & Amy's wedding at the 99th Precinct.
- He does it within 30 minutes; and tells them that if they don't like it, he will kill himself.
- Amy thanks Charles and asks how she can ever repay him. Charles says:
"Get pregnant. Use your body to give the world more Jake."
Season Six[]
Honeymoon[]
- Upon Jake and Amy arriving at the resort where they will be spending their honeymoon, a greeter brings them their drinks along with a lovers' toolbox from "Mr. Boyle."
- It's revealed that literally everything in "Charles' box of nightmare" could be used to tie up a person.
- Holt discloses later that he was able to escape from the restraints Jake and Amy used with some of the lube Boyle sent them.
Casecation[]
- Charles helps Jake set up a Paris setting for Jake and Amy's 1-year anniversary. Charles also wants to stay and serve them cheese and grapes but Jake conveys to Amy that Charles will be leaving now. Charles comments:
"Fine. Enjoy your weird anniversary with just the couple, you selfish jerks."
- Charles doesn't leave and instead hangs out outside of the room. When he's caught, Jake yells at Charles to go home.
Season Seven[]
Pimemento[]
- Holt asks Jake and Amy about their weekend, and Amy mentions that they bought a couch. Charles then gets all excited and asks them to tell him everything.
Ding Dong[]
- Charles somehow senses that Jake and Amy successfully got pregnant.
Admiral Peralta[]
- When Jake and Amy announce Amy's pregnancy to the squad, they're met with minimal reactions, including from Charles. Jake then says that they're having twins, which promptly causes Charles to faint. Jake then says that he was kidding and that he wanted to see Charles faint.
Valloweaster[]
- Charles Boyle
- Amy Santiago
- Charles Boyle
- Amy Santiago
Video[]
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