Brooklyn Nine-Nine has a cast of lovable, quirky and funny characters that we just love spending time with. One of them is the nervous, clumsy, and food-obsessed Detective Charles Boyle. Boyle’s most defining characteristic is his tendency to blurt out whatever comes to his mind, oftentimes not realizing how wrong it will sounds. And rarely does he figure it out on his own even once the words are out.

Over the course of six seasons, we’ve heard tons of inappropriate Boylers that never cease to make us laugh. So, here are the top ten times Boyle was unconsciously inappropriate and it was hilarious.

“HELLO, MY BIG, BEAUTIFUL BM.”

In season one, Charles was engaged to marry Vivian and his best buddy Jake was supposed to be the best man. In “Fancy Brudgom,”  Charles arrives at the precinct, enthusiastically greeting Jake with the line: “Hello, my big, beautiful BM.” Naturally, knowing that the abbreviation BM has a very different meaning, Jake immediately corrects his friend, but Boyle doesn’t seem to care or understand and just keeps talking.

Of course, in the previous episode, the meaning of STD went over Charles’s head so it shouldn’t be that surprising that he would think BM is a common abbreviation for best man.

“WE’LL CALL OURSELVES THE NIGHT BOYS.”

After the Florida incident, the Nine-Nine got assigned to the dreaded night shift, which put everyone in a foul mood. Jake being Jake, decided to make the best of a bad situation and convinced Boyle to work a robbery case with him. In an attempt to keep their spirits high, Boyle comes up with a cool name for them:

Sorry, did we say cool? Anyway, Jake points out that it sounds like a male escort service, prompting Boyle to offer some even more inappropriate names like the Midnight Men and, last but not least, the Dark Stallions. Jake made the smart call and went with the Night Boys, being the lesser of three evils.

“LOOKS LIKE YOU AND I ARE IN A GOOD OLD-FASHIONED SUCK-OFF.”

In the season three episode “The Cruise,” Rosa and Boyle get into a “friendly” competition for the apartment of an older woman that was recently murdered. Rosa brings the landlord down to the precinct in order to butter him up to give her the apartment and Boyle sees right through it. He confronts Rosa, brags about the Boyle family’s incredible ability to suck up, and then for some reason he says this:

When Rosa insists that he stops calling it a suck-off for reasons obvious to everyone but Boyle, it takes a few moments for Boyle to get a clue.

JAKE: “TIME FOR ME TO GET OUT THERE AND SPREAD MY…: BOYLE: “LEGS.”

In season two we were introduced to something called the Jimmy Jab Games and in the cold open of that episode, Jake and Boyle have a conversation about Jake’s feelings for Amy after Boyle overhears Jake asking Rosa for her friend Katie’s number. Jake claims he no longer has feelings for Amy, adding “it’s time for me to get out there and spread my…”  wings, is what he would have said, but Boyle interrupted him with “legs.”

Baffled, Jake repeats the full sentence, Boyle attempts to argue that it’s basically the same, to which Jake hilariously replies: “No, not either. Only wings.” Cue upbeat music. We have to give props to Boyle though for managing to make this sentence awkward by simply uttering one word.

“MY FANTASY THREESOME.”

Boyle’s tendency to blurt out inappropriate stuff is unmatched. Somehow, he manages to make every social situation uncomfortable as soon as he opens his mouth, like, for example, a regular morning briefing. On one such occasion, Terry told Boyle, who was the primary on a case, to take Peralta and Diaz to work the case with him.

Rosa being the object of Boyle’s romantic attraction and Jake being his best friend, Boyle came up with the most awkward way to express his excitement: “Yes. My fantasy threesome.” Both Rosa and Jake turned around to glare at him, prompting Boyle to add: “Of cops on a case.” And we can’t help but wonder does he hear the words that are coming out of his mouth.

“I BET YOU’RE AN AWESOME FLUFFER.”

In the episode “The Last Ride,” faced with the very real possibility that this might be their last case together, Boyle and Jake decide to go all out on a seemingly minor case and do all the things they’ve ever wanted to do. As it turns out, however, the case is much bigger than they expected and they soon find themselves working a drug case.

Because Jake was an avid bicyclist, the two hatch a plan to send Jake undercover as one of the bicycle heroin-delivery guys. Jake brags about the fluffy tricks he can do with a bike, to which Boyle replies: “I bet you’re an awesome fluffer. I bet you fluffed those other riders right out of their biker shorts. I could picture you as a teenager fluffing all of New York City.” Apparently, Boyle was unaware of the meaning of the word “fluffing.”

“AND A DRY BOY IS A SMART BOY.”

Boyle’s ability to say something cringy at every turn without even realizing he’s doing it is quite impressive. In the season four episode “The Fugitive” he made the Flo-Tec performance polo shirt with moisture-wicking technology sound even dirtier by adding: “and a dry boy is a smart boy.”

According to Amy, Boyle’s been saying that all day and he’s gotten nothing but negative reactions. However, Boyle needed to hear what his best friend Jake thought of it. Spoiler alert, he hated it. Someone seriously needs to take the time and finally teach Boyle what a cool catchphrase is.

“FROM NOW ON, THE ONLY BLACK MALE I WANT ANYTHING TO DO WITH IS YOU.”

When Terry’s angry ex-girlfriend shows up to audit the precinct, the Nine-Nine fears she will use her revenge for the audit. Boyle and Holt decide to blackmail Deputy Commissioner Grayson, but change their mind at the last moment, leading to this hilarious exchange between the two men.

Captain Holt reassures Boyle that whatever happens to the Nine-Nine, they will feel better knowing that they didn’t compromise their morals by resorting to blackmail. Boyle’s response is both awkward and hilarious: “From now on, the only black male I want anything to do with is you.” Classic Boyle.

“MY DREAMS ARE COMING TRUE. YOU AND ME GETTING MY LADY OFF TOGETHER.”

The season three episode “Boyle’s Hunch” is full of uniquely Boyle lines. After meeting his soulmate, a fellow foodie named Genevieve, Boyle vows to get her out off prison by proving her innocence with the help of his best friend Jake Peralta. In all the excitement, Boyle makes a very inappropriate and uncomfortable remark to Jake, saying:

To which Jake replies “you know how that sounds, right?” but we’re willing to bet that he really doesn’t. Somehow in Boyle’s mind, this is a perfectly normal thing to say.

“I’LL DO ANYTHING TO PERK UP MY LITTLE MAN.”

In the season four episode “Captain Latvia,” Boyle teams up with his best buddy Jake to track down a Captain Latvia action figure that he promised to get his son Nikolaj for Christmas. It turns out the Latvian mob has the toy, so the two stake out their warehouse. Jake wants to wait for back-up to arrive, but Boyle gets out of the car, takes off his pants to scooch between the car and a truck, and then yells out to Jake:

Jake immediately points out what we all are thinking: “you gotta know how gross that sounds in your underwear,” but amazingly Boyle does not.