K I live in canada, am 20 and have no convictions or run ins with the law.

Last month, I was caught shoplifting. I have a court date set for that on April 20th. This happened in guelph and the court date is in guelph.

But I was stupid,
The other day, I was caught shoplifting AGAIN. Different place/town compltely. Court date set for may 9th.

My Questions are;
What is likely going to happen to me?
What's the worst that will happen to me?
Is they are chance I can get off with out any convictions on my name
Will I experience any jail time?

Also;
Any suggestions?

You are a repeat offender. Most probably this will disqualify you from the diversion program.

I would expect fines, some sort of probation - probably no jail time (depending on the amount).

The Court will be concerned because you learned nothing from your first arrest.

I believe you will have a conviction on your record - the Court is not going to waive that for a two time shoplifter.

Don't understand why your heading said different circumstances? In both instances you were caught red handed stealing. The judge is not going to go lightly with you nor will you get the first offender deferred status either.