Let's see if I can do this quick before KHR 258 comes out.

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A picture of the funniest face:

This is as close to Yamamoto shouting "VODKAAAA!" as I think we're going to get. (Except he was still smart enough to use some form of parachute.)
A picture eating:

It's pretty much impossible to find a colored version of this pic that doesn't make the popsicles look extremely phallic, but oh well.
A picture with an animal:

Actually, this one has three animals if you count the shark over on the left. BECAUSE SQUALO'S A SHARK. GET IT? HAHAHA I'M SO WITTY.
A picture with the opposite sex:

Aside from Reborn, you could make the argument that he's surrounded by girls in this picture. Or close enough, anyway.
A picture you’d have sex with:

That last panel never fails to instantly turn me on. :/
A picture of your favorite outfit:

Or anything where he's rocking that shirt-and-loose-tie look, really. Though frankly, he looks good in anything.
Happiest picture:

HE'S ALWAYS HAPPY, IT WASN'T EXACTLY HARD TO FIND A PIC.
Saddest picture:

It's a lot harder to find a sad one, but he looks pretty broken here. TYL!Yama really brings the angst. ;_;
Half-naked picture:

I just like this one because he's being a goddamn tease. DAMMIT WHY IS HE FOURTEEN.
Picture of an outdoor activity:

Punting Lambo at Hibari's face was always one of my favorite outdoor activities too.
Favorite picture:

He is just hot in this picture. HOT. And Gokudera is too. I dunno, every time I look at it I just find it hard to stop staring.
HIT ME UP IF YOU WANT A PERSON YO.
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And so dead once Lambo hits Hibari.
XD Wanna do me?
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WHAT ARE YOUR THOUGHTS ON SHOUICHI? 8D
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Srsly! BUT HEY. YAMAMOTO DOES HAVE A SUPER ARM.
Shou-chan huh. :D I can do that. ^_^v
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:DDD