Only if officers have reason for probable cause. Seeing as how you dropped the charges the first time, you can quote precedence when filing a RO as you can claim you don't feel safe. The only way he can go to jail on assault charges now is for an unrelated case or, god forbid, he violates the order and assaults you. In that case, he'd be charged with both and depending on his record and severity of the attack he could face jail. As fr as being charged in court when trying to secure the RO, it's unlikely because there would have to be an investigation first.
