Better Advice To Help Teenagers Socialize

I often see teenagers who have difficulty socializing with their peers.  Anxiety is often at the heart of this difficulty. In general, these teenagers are occupied with ideas of being judged, rejected, or attacked in some social sense (For example: having rumors spread about them). After having this problem for a while teenagers usually seek help or someone notices them struggling and tries to help them. This help usually comes in the form of advice about how to start conversations, keep them going and avoid silences.  Although this is well intentioned I believe that it can do more harm than good. 
Teenagers who try to take this kind of mechanistic advice on conversations start to see talking to their peers as a task that is done well or done badly. They spend time before and during conversations trying hard to prepare for what they are going to say next, how to react well, how to keep the person they are talking to entertained and they loose sight of the real function of conversations! The real function of talking to people in casual, non-goal oriented ways is to establish an emotional connection. So, instead of feeling for a connection, something that may or may not happen (and it's OK if it doesn't happen), these anxious teenagers spend their time evaluating their performances and even if they are successful in these attempts they end up missing an important point and it can end up feeling fake. So, even if they end up making a friend that person is not friends with the real them! 
Friendships and emotional connections are not forced. They are not jobs well done.
Better analogies for helping teenagers understand conversations are improvisational art works like jazz, unstructured dancing, rap battles, and visual art with an element of randomness and chaos. It's not about forcing it, making it happen or doing a good job. It's about allowing the experience to unfold in a spontaneous, non-intellectual, non-rational way. The outcome of these kinds of artistic expression is not know before it has already started to be created. Even novels are often written in this way. 
Trying to predict where improvisational art is going to go and what is going to come out of it is obviously a ridiculous task! You'll never be able to! So the message is this: don't try and don't try not to try. There is no way to prepare for a genuine and spontaneous conversation that results in an emotional connection. 
Explaining conversations to teenagers in this way can help them to shift their attention and stop them trying to make cumbersome advice work. 
Some teenager may be afraid that this kind of approach to conversations leaves the door open to may too many mistakes. Here the common anxieties kick in. Fears of rejection, judgement, offending, attacks. One of the most helpful things to tell teenagers when this comes up is: Yes! Those things will eventually happen to you. They happen to everyone. Forget about avoiding these experiences. Surrender to them. Going through experiences like that can be very helpful to improve your conversations if you allow yourself to suffer them, think about them, learn from them, and talk to trusted people about them. Again, this is something you don't have to try to do. It happens automatically when you feel fully, reflect on, and come to an understanding of your experiences. 
This way of explaining conversations also undermines a common fantasy related to the idea that conversations are jobs well done and it is this: If I do this job well enough I can avoid everything that I am afraid will happen in the conversation. This is totally wrong and the opposite tends to be true. The harder you try, the longer you're stuck in a situation where these things are likely to happen to you. At this point parents can be helpful and say something like: Yes, you will get hurt. But, you're strong! And you can take it!