Quotes: Unsettling Gender Reveal

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    Anime and Manga 

Tsubomi: So cool... [Itsuki]'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...
[...]
Servant: Itsuki-ojousama, here's your tea.
[...]
Tsubomi: "O-Ojou-sama?!"
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

...Where are your boobs?!
Hinoe, Natsume Yuujinchou

    Fan Fiction 

I told you before... I am not a woman! I'm a man!

    Film - Animated 

So, being a ladybug automatically makes me a girl! Is that it, flyboy?!
Francis, A Bug's Life

    Film - Live-Action 

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?!
Ace Ventura, Pet Detective

Oh, my name is Tim. I'm always available. By the way, I also do engine work on BMW's.
Transvestite Hooker, Bachelor Party

You're in Bangkok, honey. There's a reason they don't call it "Bangcunt".
Kimmy, The Hangover

Angela. Such a lovely name. Why I believe it means "angel!" Why, yes, I'm sure it does! I know you're going to like that name, won't you, Peter?

Jerry: I'm a man!
Osgood: Well, nobody's perfect.
Some Like It Hot, final lines of dialogue

    Live-Action TV 

    Professional Wrestling 

Oh, sweet Jesus, she's got a penis.
Mark Henry, WWE Monday Night RAW

    Video Games 

Not another dude...
Kagura Mutsuki upon confirming Amane Nishiki's measurements, BlazBlue: Chrono Phantasma

"Oh, my stars and comets! He's a she!"

Bridget: Hey, what's wrong with you? You suddenly went limp right in the middle of the fight...
Johnny: Ahh... Johnny... What have you done... You... you're a guy, aren't you!
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...
Guilty Gear XX, in which Johnny learns the truth about the former Trope Namer

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!?

    Web Original 

Wait, Bridget is a dude?
Oh god.
Oh God!
OH GOD!
— A new Anonymous that needs to lurk moar

Hal: Hey baby, what's your name?
Birdo: (in deep manly voice) My name is Susan.
Hal: Ahhhhhhh!
(Susan blows a kiss at him)
Bowser's Kingdom episode 6

That's a dick!
The Cinema Snob reacts to the aforementioned Sleepaway Camp

Kyoko Kirigiri: Chihiro Fujisaki's corpse was moved into the girls' dressing room, but in reality the crime scene took place in the boys' dressing room. The reason for this... is because Fujisaki... isdesignatedmaleatbirthalthoughicannotsayeitherwaywhethertheyidentifyaseitheroranygenderbutnonethelesstheiridrecognizesthemasmale.
Everyone: (mass gasping)

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?

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!!!
M.U.G.E.N user zigg4d gets a Bridget dropped on him

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?!

Natascha: How about ve get room and continue zere, Miss Kenshin?
(Kenshin blinks out of confusion)
Kenshin: Uhhhh....
Natascha: ?
Kenshin: I'm a boy.
(Natascha looks confused)
Natascha: ...vat.
Kenshin: Yeah.
Natascha: ...you very look like voman.
Kenshin: I get that a lot.

Alice: How about we raise the stakes? Winner gets to savor my tenderloin.
Mr. Krabs: (screams)

    Western Animation 

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?
"Lady": Pre-op.
Quagmire: Whoa, transvestite! Back off!

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!

Brian: AAAAAAAAAAAAAAAAAGGGGHHH!!!
Stewie: What!? What is it!?
Brian: I HAD SEX WITH HER!
Stewie: WHAT!?
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"