We might take a hint from the Mormon community, which sends young men off to practice speaking to strangers by encouraging them to join their Church. If you take the religious part out, you're left with a degree program in social courage.
I'd wager that the opportunity to learn social courage is declining for all students -- a result of technology, helicopter parenting, and an ever-increasing focus in schools on the "basics" (to the detriment of art, music and theater, which are more likely to push kids out of their comfort zones). Social situations are getting easier for kids who can now avoid having difficult conversations in person simply by texting or using Facebook, but there may be a large cost when it comes to long-term life skills.
Comments and feedback can be sent to firstname.lastname@example.org