This being your second offense, you COULD potentially be going to the Juvenile Detention, however if you get an attorney to represent you, especially for (an) item(s) amounting to just $40, detention can be avoided altogether, along with other conditions that the court may impose if you're not properly represented.
At your age, the best outcome would be if this experience taught you a lesson. :)
Its a possibility and a great deal will depend on other factors. Retain local counsel to represent you. Good luck.
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Based solely on what your question states, the answer is no. I do not think you should worry about going into custody. Your first offense was almost five years ago. The current offense seems very minor. I would expect you to placed on some form of diversion, perhaps HOP, wherein you would have to complete some community service and probation would monitor you for grades and school attendance for perhaps a year.
I would not overlook fighting the merits of the case, such as via a motion for civil compromise to have the case dismissed up front, so you do not have to deal with HOP at all (or custody time).
You may want to do an online shoplifting course now (through the National Association of Shoplifting Prevention). There are two courses. One is about four hours and costs about $40. Complete it and print out the completion certificate and then show it to your counsel and make a copy for the judge.
No but continue doing this and you may end up in juvenile hall!
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