A/N: So, these are just going to be short little snap shots of Dean and Lucifer's friendship, and will eventually become Lucifer/Dean. I'm hoping to update pretty frequency, considering this is more of a low pressure writing exercise then an epic, super planned out story. The title is taken from a concept explored in Dr. Seuss's novella "Oh the Places You'll Go!" I've decided to just go with memorable titles that amuse me rather than agonizing over finding one that's just the perfect fit!

Please read and enjoy!

Sammy wasn't out yet.

Dean was waiting in the school parking lot, lounging against the Impala like he had every right to be there, ignoring the weird looks he was getting. Middle school had ended almost an hour ago, but his little brother was taking his sweet time getting out. Leave it to Sammy to try and draw out school as long as possible. Dean shifted and scowled, antsy to hit the road, to get somewhere not so boring and oppressive. He, at least, didn't want to stick around school any longer than he had to. Never mind that the school wasn't actually his own.

What was taking Sam?

"Problems, Winchester?" Dean very nearly dropped his keys.

He turned to see a blond dude leaning on the hood of his baby. "Whoa dude," Dean snarled, "hands off the car."

The guy straightened and put his hands up, a disarming smile dancing across his face. Dean would've apologized for snapping, if the guy hadn't looked so goddamn smug.

"Easy, there. I just came to tell you that your brother's staying late today."

Dean squinted at the guy. The name alluded him, but he was pretty sure Blondie was a senior at his school. "And how do you know that?" Dean's voice held a tad more suspicion than was truly warranted.

"He's in the debate club with one of my cousins." The guy shrugged. "They won't be done 'til around five. I saw you standing out here, and figured Sam forgot to tell you or something."

"Oh." Dean deflated, feeling like an ass. Here someone was trying to help him out, and he bites the dude's head off. Not cool. Even if the guy did seem unnaturally smug. Maybe his face was just stuck that way?

"Well, thanks. I guess." The guy hummed, and turned to leave. Dean made a snap decision. "You need a lift anywhere?"

Blondie looked back at him, surprise overriding his default smugness. Dean decided he liked that. The guy got over it, flashed some teeth his way, and said "There's a new diner in town I've been wanting to try. Would you be willing to kill some time with me?"

It's nowhere near dinnertime, but Dean's got nothing to do, he's sick to the teeth of waiting on Sammy, and their apartment's cold and empty. Plus, Dean's been told he's got a bottomless pit for a stomach, so…

"Why the hell not?"