Two excellent recent articles provide very different perspectives on anonymity and free speech. The first, Stop Spying on Wikipedia Users, explains why anonymity is needed for free flow of information. The second, Changing the Way We Yak, shows how harmful anonymous speech can be when exploited by irresponsible jerks, who are far too plentiful.
Freedom of speech resembles freedom of drinking. For the most part, Americans are free to drink whatever they like. It does not follow that it's OK to drink gasoline. Likewise, free speech does not entail it's OK to make rude remarks or shout in someone's ear.
It is hard to know, but worth considering, whether the problem of rude or intimidating speech is getting worse. When I was in high school, there was a kid named Felix who had something wrong with his brain. He had a metal plate on his head. Some other boys at the school took delight in teasing him, calling him Felix the Cat, and meowing around him. If Felix got upset enough by this, which was not hard to accomplish, he would have a screaming fit, greatly amusing his tormentors.
"One can only hope their pleasure outweighed his pain," a utilitarian might say. But the relative amount of their joy and his suffering is not the issue. However much they enjoyed it, their taunting him was very wrong.
Back then, it was not hard to identify the abusers of freedom of speech. But now, with the advent of anonymous social networking apps like Yik Yak, inconsiderate idiots can cause trouble anonymously, with almost no chance of being identified. (For the uninitiated, Yik Yak enables anonymous public chat in a limited geographical area like a campus.) The ability to be rude anonymously encourages abusive behavior by those who are restrained from such activities by fear of getting caught, probably resulting in more such anti-social behavior than in the past.
What is the solution? Should people be allowed to keep their faces covered in public, enabling those engaging in offensive behavior to escape identification? Should anonymous rudeness be legal? Attempting to outlaw all bad behavior is unlikely to succeed. But people should be sufficiently educated that they understand freedom of speech does not license rudeness any more than freedom to consume whatever we want makes it all right to drink gasoline.