Your behavior is limited only by a court order directed at you and with which you have notice. Moreover, your taking care to avoid contact even when not ordered can hardly amount to any kind of violation. The violation claim sounds more like some kind of intimidation.
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You probably cannot get into any trouble by being in contact with him.
Your roommate can get in trouble, however, if you are contacting the person at her past. She cannot have you do what she is prohibited from doing. So if you contact this person on her behalf, she could be in trouble.
If you found this Answer to be helpful, please mark it as such. Remember, however, free advice is worth every penny you paid for it. This is only generalized commentary on your question. It is not to be taken as legal advice. I am a lawyer – but not your lawyer! Even "in person" interviews leave attorneys with plenty of questions – the Internet makes it crazy! Thank you Chuck Watson 217.544.6165