He broke the restraining order so there is nothing for you to testify for. It is him against the state at this point as long as the state has the evidence. I'm speaking from personal experience. If he contacted you over multiple days, those are treated as separate incidents. So the charges rack up quickly and are taken seriously. You are also treading a fine line by keeping in contact with his family. No messages can be given or taken. So asking about him is probably okay. Asking his mom to give him a message is a big no-no.