1. I go to a college that sends a lot of people to high-profile jobs and that also has a reputation for heavy alcohol use. I don't think that there's going to be as much airing of indiscretions as you guys think. There are basically 3 groups:
-Maximalists who do crazy things but don't reflect on them. Think Bill Clinton.
-Kids very conscious of their status. They have the money to pay for search result erasures. They consciously try to get rid of any paper/picture trail. They make their social networking pages oriented toward public examination from the very beginning. At the political publication I work on, for example, graduating seniors have the option to delete or remove the byline from any of the pieces that they wrote.
-Introverted people who try to "stay off the grid" as much as possible. Even as undergraduates, they make sure that they avoid saying controversial stuff in debates, since it will likely be accessible in the future. They don't really use Facebook or go to parties. They don't do extracurricular writing and try to avoid associating with organizations (college or otherwise) until they're willing to take any future consequences.
2. According to a different podcast I heard, P. Diddy twittered a tantric sex session. So, yeah, the Twitter date barrier has been surpassed.