There is nothing more scary than being in a room full of strangers and you are there to entertain them by drawing a likeness of them that beings out all of their flaws. Of course these “flaws” are what makes them unique- gives them “character” thus the word caricature art
Here is the trick… No one wants to be made fun of in public with people who they may or may not have a relationship. The caricature artist has an unspoken trust with his drawing subjects. You need to quickly size up the person and get a feeling of how sensitive they are with the features that God has given to them. Rule of thumb is making women younger and prettier. They will love you. The guys are another story. If they are being a jerk , then you have liberty to return the favor in kind. Just make sure they aren’t the type to punch you in the face. Reading the room can give you a lot of information on if the people are having fun and if someone gets loud or obnoxious, they will protect you.
People will save caricatures for years. I have been in houses of total strangers and seen my work hanging on their walls and I would enquire what occasion the caricature was drawn. It never stops amazing me on how people will place on a great memory and my caricatures are a physical reminder of such good feelings.