Hi Cee! I'm Dawn, auxiliary mod. I've got three characters here, two of which I'm positive would be interesting to put with Dean in a thread, or two or more...
First we have Anthony J. Crowley evil_ish. AKA: Crowley, Crawly... He's the primary demon in the book Good Omens if you are not familiar with him. He likes humans quite a bit, helped stop the Apocalypse alongside the angel Aziraphale, and wears sunglasses pretty much all the time. I think this could have potential for Dean (I can't remember where you're pulling him from in the series versus this actually happening, though) because I know there was a demon named Crowley in the SPN-verse and a yellow-eyed demon (Azazel). Could be fun!
Secondly is Mad Sweeney suibhne_geilt. He pretty much just goes by Sweeney. He's pulled from the book American Gods and is an extraordinarily talk leprechaun. He's kind of degenerate, though. Loves to smoke, swear, drink, fight and wear highly offensive clothes. Oh, and by tall, I mean he's just short of 7 feet.
Lastly, who I'm not sure how he would interact with Dean... probably try to flirt with him... is Jack McFarland just___jack of Will & Grace fame. He's flamboyant to a fault and doesn't seem to have a filter between his brain and his mouth.
You can find their profiles in their journals. Let me know if something doesn't work. Also, you can reach me on AIM pretty much any time of the day unless I'm sleeping at DawnM1227. Welcome aboard!