I have dealt with a lot of emotional law students and both men and women cry. Men don't seem to apologize about it as much, in my experience. I would be taken aback a bit if a student wanted a witness - but I would probably allow it. It would make me more reserved. I would probably wonder why they needed a witness to meet with me and if they were trying to set up a witness for some further action to stop something they did not like. I understand that was not your intent - just throwing in another perspective. It does sound like you are in a difficult situation.