Legal Question in Criminal Law in New York

A "no illegal contact restraining order"? I am not sure what that is, however, the penalties for violating a valid order of protection will depend upon so many factors that it would be impossible to answer your question without more information. For example, different locales of the State of New York prosecute violations of orders of protection differently. Moreover, if your boyfriend has a past criminal record that will likely increase the probability of Jail time. Typically in the New York City area, a first time violation that does not result in personal or property damage can be pled down so that the offender does not do jail time. Ultimately the prosecutor makes a decision as to whether to offer a no jail time plea, and the Court decides whether to accept it.