Jake: Okay, if we wanna get past O'Sullivan's ma, we need undercover personas. I'm thinking you will be Maxwell Maxwell, international playboy and black ops specialist. He'd had affairs on every continent, but his true mistress is danger.
Captain Holt: I thought you learned your lesson about turning police work into movies.
Jake: Yeah, I did, but this is a movie about reform. I mean, isn't that a movie you'd wanna see?
Captain Holt: The only movie I wanna see is called The World of Mosses. It's a documentary about the world of mosses.
Jake: It sounds bad.
Captain Holt: Now, we will go in dressed as gas company employees named Mitch and Henry.
Jake: Ugh. At least tell me I'm Henry.
[later:]
Jake: Hello, ma'am. We're from the gas company. My name is... Mitch.

Jake: Okay, to get into the basement, we're gonna have to distract her, so here's what I'm thinking. Maxwell Maxwell turns on the charm. Unbutton your jumper and say, "The thing about gas lines is, "the pressure builds and builds and it just needs a little... release." [moans] You don't have to make that sound, but if I were you, I definitely would.
Captain Holt: No one will be talking about release or making the sound of a rodent in labor.
Jake: It was a sensuous moan, but fair enough.

Kevin: Raymond? What are you all doing in here?
Captain Holt: Um... Peralta's watching porn.
Kevin: What?
Jake: What?
Captain Holt: Peralta's watching a handyman repair a squeaky door and then [bleep] his customer.
Kevin: Is that true, Jake?
Jake: ... [quietly] Yes.
Kevin: I wish I could say I was surprised.
Captain Holt: Told you it was a great cover.
Jake: Not for me!

Rosa: What am I doing?
Jake: You, Charles, and Scully will be here, distracting Kevin and making sure he doesn't know Holt's working.
Captain Holt: And who will be on Cheddar duty?
Rosa: I mean, can't we just distract him with a bone?
Captain Holt: Bone? Bone?
Jake: Yeah.
Captain Holt: [yelling] Bone? Cheddar's not some street rat.

Captain Holt: Now, when we originally wed, we didn't know how long gay marriage would be legal, so we had a somewhat rushed ceremony.
[flashback:]
Justice of the Peace: Do you, Kevin...
Kevin: Yes.
Justice of the Peace: And do you...
Captain Holt: Yes. Yes, we do. We're married.
[present:]
Captain Holt: Kevin has always regretted it, so we're having a vow renewal ceremony. This time, we're pulling out all the stops. It's will be a truly extravagant affair.
Charles: Oh, how extravagant are we talking? Champagne pyramid?
Sergeant Jeffords: Destination wedding?
Jake: Celebrity officiant?
Captain Holt: We got the salad forks. Can you believe it, a second fork? Who do we think we are? [laughs] Oh, no. You're shocked at how garish it is. Now I don't even wanna tell you the other surprise I have in store for Kevin.
Jake: Wait, let me guess. You're getting bread plates?
Captain Holt: Don't be absurd. We're not crazy. No, the big surprise is... I'm retiring from the NYPD.
Sergeant Jeffords: Wait.
Charles: What?
Jake: Why did you lead with the salad forks?

Captain Holt: Lastly, on a personal note, as many of you know, Kevin and I have recently reconciled.
Jake: Noice. Somebody's getting some.
Captain Holt: It's true. I am.

Jake: There you are. Why are you hiding?
Captain Holt: Oh, I was just looking at pornography. I felt an urgent need to watch some men taking a bath.
Jake: What?
Captain Holt: Okay, fine, you caught me. I was checking my email.
Jake: And that's worse than watching porn?
Captain Holt: Much worse. Kevin can't know I'm working on our special day.

Captain Holt: I'm gonna check those CompStat numbers right now. I'm just gonna click on this video link entitled "Handyman fixes squeaky door, [bleep] customer."
Jake: Oh, my God.

Rosa: We wanted to apologize.
Amy: And if you wanna gloat about how you outsmarted us, go ahead. We deserve it.
Captain Holt: I won't be doing any gloating. I mean, I did last night. I went home and had a drink to toast to your humiliation. But it didn't feel right, because I had no one to toast with, no one to share my glee. I had won, but I was alone. And I realized, this is exactly what I'm doing to Kevin. Trying to win therapy. And it hit me. I care so much about winning that I've lost everything.
Rosa: Tell Kevin how you feel.
Amy: It's raining. You could run to him.
Captain Holt: This is the real world, Santiago. Relationships end in unsatisfying ways every day. People don't run to each other in the rain.
Kevin: [o.s.] Raymond! Raymond Holt!
Captain Holt: Kevin?
Kevin: Raymond!

Rosa: Okay, sir. This app's pretty simple. If you don't like the guy's profile, you click "dang," and if you do, you click "daaang."
Captain Holt: That sounds needlessly confusing.
Rosa: Why? "dang" is bad and "daaang" is good.
Captain Holt: Okay, let's thin this herd. Untucked shirt, no thank you. Born in San Diego, yikes. An adult named Todd? So this is what online dating is like? I didn't realize.
Amy: Realize how good you have it with Kevin?
Captain Holt: No, how it hasn't changed. You still have to pick someone based on looks and hope for a connection later. Oh, Lord, help me. I'm going for it. I'm clicking "dang."
Rosa: No. "Dang" is bad. Click "daaang."
Captain Holt: Why is this so confusing? How do I get Hot Todd back?

Captain Holt: Huh. It's the exact time we agreed to meet for our date, and he's not here.
Amy: I'm sorry. I know how you value punctuality.
Captain Holt: In my employees. But in potential suitors, I don't mind one or two minutes of tardiness. I like a bad boy. Now, if you'll excuse me, I'm going to go to the bathroom to wash my hands, in case we shake.
Amy: Ooh.

Captain Holt: Looking for someone?
Amy: Sir. Uh, what's going on?
Captain Holt: What's going on is that you were trying to manipulate me, but it is I who manipulated you. How does it feel to suckle from your own tainted teat?
Rosa: Not as bad as it feels to hear you say "suckle."
Amy: So you were never really going home with Todd?
Captain Holt: You actually think I would have relations with him? His watch has a cloth strap.
Todd: I really thought we had something.
Captain Holt: Wake up, Todd. I'm out of your league. You thought you could meddle in my personal life, but I was ten moves ahead the whole time. And now, checkmate.
Todd: Ooh. I love chess. Have you seen The Queen's Gambit? It's a TV show.
Captain Holt: Todd, I swear to God.

Rosa: Sir, if you wanna get a date off of these sites, you're gonna have to give me a little more from your profile photo.
Captain Holt: I just gave you a series of eight poses, each increasing in sexual provocativeness by one-eighth. If you wanted septiles or deciles of sexiness, you should've told me. [Amy groans] What? Why do you care so much, Santiago? I thought you didn't like the idea of me dating.
Amy: Yes, initially. But then I thought about your metaphor about how relationships are like a chess match.
Captain Holt: Mm-hmm.
Amy: And it really convinced me.
Captain Holt: That was a strong observation.
Amy: So why don't you think of this profile photo as an epic chess move?
Captain Holt: Like Vladimirov's Thunderbolt of 1987. Close the door, Diaz. I'm removing my collar stays.

Amy: Hey. What's going on?
Rosa: I'm helping Holt pick a dating site.
Captain Holt: Oh, this looks good. PhDs only.
Rosa: Uh, actually in this context, PHD stands for Pretty Huge [bleep].
Captain Holt: Oh, my. I can only assume that MDs only stands for Medium [bleep].

Rosa: Yo. You forgot your lunch.
Captain Holt: Oh. Thank you, Diaz.
Amy: Sir, I didn't realize you were still staying at Rosa's. I thought couple's counseling was going well.
Captain Holt: Not anymore. At Kevin's request, I offered to reduce my work hours by 26%. Kevin countered with 50. Which I countered with 30. Then Kevin says 40...
Amy: Seems like a lot of math for therapy.
Captain Holt: That's what Dr. Cheryl said... which is why we fired her, and now we're working with Dr. Ramanujan. He's a physicist with a nice, concrete worldview. Anyway, Kevin refuses to budge from 36%. And I'm starting to worry that I might lose to him.
Amy: You mean lose him.
Captain Holt: No. Lose to him. Therapy is a chess match. And... I will prevail.