Quagmire: Hey there little lady. Why don't you turn around and show me your lower east side.
"Lady": (in masculine voice) Sure.
Quagmire: Whoa, transvestite! Back off! Wait a minute, pre-op or post-op?
Quagmire: Whoa, transvestite! Back off!
Bridget: Hey, what's wrong with you? You suddenly went limp right in the middle of the fight...
Bridget: Sure am. This appearance... Well, it's kind of a long story.
Johnny: I can't believe I just tried to seduce another man...
"Oh, my name is Tim. I'm always available. By the way, I also do engine work on BMW's."
— Transvestite Hooker, Bachelor Party
Wait, Bridget is a dude?
— New Anonymous that needs to lurk moar.
"So I was looking up Shion's story... until I found out 'she' was a 'he'... GODDAMN YOU SNK AND YOUR POINTLESS SQUAREENIX-STYLE GENDER BENDING!!!"
Jerry: I'm a man!
Osgood: Well, nobody's perfect.
— Some Like It Hot, final lines of dialogue
"Oh, sweet Jesus, she's got a penis."
— Mark Henry, WWE Monday Night RAW
"Fascinating creatures. Look like women, but they have... boy parts. I'm not attracted to them! They're just... confusing."
Peter: If you could be stranded on a desert island with any woman in the world, who would it be?
Quagmire: Taylor Hanson.
Joe: Taylor Hanson is a guy.
Quagmire: (laughs) You guys are yankin' me. "Hey, let's put one over on Quagmire."
Peter: No, he's actually a guy, Quagmire.
Quagmire: ...What? That's insane. That's impossible. ...Oh god. Oh my god. I've got all these magazines! Oh god!
"What the... That's it. That's it. Einhorn is Finkle. Finkle is Einhorn! EINHORN IS A MAN! *remembers that he kissed Einhorn* OH MY GOD!! EINHORN IS A MAN?!"
"If it's pretty, f*** it. There is no gay."
"...Where are your boobs!?"
— Hinoe, Natsume Yuujinchou
Hal: Hey baby, what's your name?
Birdo: (in deep manly voice) My name is Susan.
(Susan blows a kiss at him.)
— Bowser's Kingdom episode 6
Tsubomi: (about Itsuki) So cool... he's so cool...!!
Erika: Oi... if you don't want to get into a big shock, maybe you should seek someone else other than the Student Council President...
Tsubomi: ... W-what!? What was that about!? *other students glare* S-sorry...
Erika: I'm telling you, the Student Council President is...
Tsubomi: You're disturbing his training. Could this be... first love!? Even if you say otherwise, my heart is burning!!
Erika: Well, I dunno...
Erika: The student council president is a girl. The entire school knows that. You were busy dozing off so you probably did not listen.
Tsubomi: The student council president is a girl... My first love... ended in three minutes... T_T
Natascha: How about ve get room and continue zere, Miss Kenshin?
(Kenshin blinks out of confusion.)
Kenshin: I'm a boy.
(Natascha looks confused.)
Natascha: ...you very look like voman.
Kenshin: I get that a lot.
"So, being a ladybug automatically makes me a girl! Is that it, flyboy!?"
— Francis, A Bug's Life
Alice: How about we raise the stakes? Winner gets to savor my tenderloin.
"Not another dude..."
—Kagura Mutsuki, BlazBlue: Chrono Phantasma, upon confirming Amane Nishiki's measurements
Polnareff: Hey Mr. Joestaaaar! Hohahoi! Oh boy, man oh man. I was totally tricked. [Nena] turned out to be a boy.
Joseph: Hahaha, that's too bad! Can't expect things to be easy in the world we live in. Especially for someone like you.
Polnareff: What the hell does that mean?!
Stewie: What!? What is it!?
Brian: I HAD SEX WITH HER!
Brian: I HAD SEX WITH HER AT THE MARRIOT!
Stewie: AAAAAAGGHH! WHY!?
Brian: I DON'T KNOW! I DIDN'T KNOW IT WAS HER!
Stewie: OH MY GOD!
—Family Guy, "Quagmire's Dad"
Saika Magoichi: My, my... there are some beautiful girls on the battlefield today!
Mori Ranmaru: Who are you calling a girl!?
Saika Magoichi: Gah! I must be losing my touch! How can I make that mistake!?
— Samurai Warriors 2
You know I'm in love with this chick
Because it seems we really click
There's no room for doubt
I think I'll ask her out
Wait... did you say she has a dick?