Legal Question in Criminal Law in Massachusetts

It sounds like the manager is trying to extort money from you in exchange for her not reporting you to the police. Even if you pay it, there is no guarantee that the manager will not call the police anyway. Do not talk to the police to "tell them your side of the story"; the police won't believe you and will only use your statements against you in court. $30-$40 worth of stuff over the course of a few months, assuming that any taking that occurred before the most recent time you were caught can be proven, is still squarely a simple shoplifting charge.

If you are an adult when the incident occurred for charging purposes (17 years old or older) with no record, a shoplifting conviction will carry at most a $250 fine, but usually simple shoplifting is dismissed upon court costs, community service or a combination of the two. If you are a juvenile, you could technically be committed to the Department of Youth Services until age 18, but the usual disposition is probation.

Call a lawyer to discuss the specific facts of your case to figure out the best course of action. Even though shoplifting is a minor offense, it can have significant and long-lasting impacts on your life. Get a lawyer and handle this the right way.