Why did Jeb cross the road?

[viktor19]

A philosophical one, eh?

I'm asking you to help me with this!

[Pseudo Gold]

Because he crashed. Again.

[SkyRender]

Because the road happened to be below his craft at the time. He crossed it again 30 minutes later on his next orbit, too.

[EtherDragon]

Why, to get to the launch-pad of course!

[Jovus]

Because there was a booster on the other side.

[Engineer of Stuff]

He saw a shiny new experimental plane that had never been flown before.

[Vanamonde]

To get to the Games sub-forum (Moved.)

[Lhathron the Elf]

He was walking away from an explosion with all of his bad-@$$ery.

[Norpo]

Because the sun was over there, and it's very well known that kerbals are attracted to shiny objects. (See description text for Moho)

[Cripion101]

Because it was there to be crossed

[Bill Phil]

To plant his metaphorical flag in the metaphorical dirt.

[Rainbowtrout]

To go to the bakery, to buy some bread, then he walked across to the mechanic to pick up his car. Then, he remembered that his anniversary was coming up, causing him to quickly buy a ring for his wife. Then he taped himself to a booster.

[Xannari Ferrows]

Because he was sad...

His job at the space center, lost. All he wanted to do was experiment a little. He argued that's what science was about.

There was nothing for the poor kerbal. He comes up to a road; a busy one at that. He is aware of the dangers ahead, and he steps out onto the asphalt, his life empty of hope.

Jebediah wants to get to the... other side...​

[Janos1986]

Because the rocket malfunctioned. It would have used to get to the other side instead.

Also:

(CHOPPITY CHOP)

Jebediah wants to get to the... other side...​

[WinkAllKerb'']

Because (NOT Sonic the) hedgehogs needs a hand or two.