My boyfriend was court ordered to look for a job that would enable him to pay child support if he did not look?

You don't have to worry about him going to jail, there is a great chance he will not go. The amount of time he is been out of the military will make a difference also, if it has been a year or less there is no way he will be sent to jail. Are you sure you can't get any assistance? 2300 a month is above the poverty line but there is still assistance out there for you.