For the past several years, I've adopted the position that going for a drive to nowhere specific with someone, especially a teenager, is a great way to get them to talk. (Sitting across a restaurant table from each other also works because no one has to cook or clean and eating has always been a social event for people.) My youngest sister, Anna (whom I've raised since she was 12) is 19 now. Anna and I go for nowhere drives a lot...and we often talk at length about culture, equality, teen issues, movies and music. Of course, this got a lot easier after Anna turned about 17. Before that, between about age 13 and 17, it seemed like all she did was cry melodramatically and wail that my husband and I were crazy.
The moral of my story is twofold: (1) we're all our coolest when we don't try so hard; and (2) my Danskos are the most gangsta, high-end, healthy foot, comfort shoes...eva.