I think as long as you're comfortable with yourself and you love skateboarding, why the fuck not bring your board everywhere? The best part of my day is bombing home from work or to downtown, bonking cracks and ollieing manholes.
Usually when someone yells Tony Hawk! or some shit I either ignore them or tell them to grow up. As for social confrontations regarding skateboarding, I'm usually glad to educate the average joe on how I feel about skating, as long as I have the time and he/she doesn't read like an idiot or seems inconsiderate. It all depends on who's asking.
A pack of us bomb to the bar every weekend after pre-drinking and have the best time skating through all the people getting wasted on our way to the pub. Sometimes we just end up skating instead! One thing about going out late at night though is you have to be careful after the bar closes. Stay with your homies if you have a skateboard, because it never fails that a crew of jock dudes are gonna mock you and cause beef if you are alone. Had a homie that got stomped the other week after being made fun of for having a skateboard... our whole crew seen the dude the other night, homie pointed him out, then one of our friends just went over and beat the fuck out of him. it was like, "thats the dude." nothing else was said and our buddy just went and fucked him up! pretty amazing.
Longboarding. I fucking hate them. they lurk the city like the plague. no joke I seen a dude in sandals, carrying groceries and going uphill. When we go skate on the university campus, there's so many good lookin broads... if I'm chilling with a crew I kind of think to myself, "all those chicks probably think we're fucking longboarders." that bums me out bigtime. I almost want to make posters that say "longboarders aren't skateboarders" and post em up everywhere to cause intrigue with the average city dweller.