Ok, I suppose I should choose a winner now. Been a bit over 24 hours. Tough call, but I'm going with zerogravityfat.
"highway to hell? son of a bitch i knew i should have turned left on i-80"
"no one's going to pick me up with this lipstick, what was i thinking?"
Both of these were win.
Dark Master was very close behind with his captions though, and an honourable mention to rumby's one too.