The only way you'd face jail on a first marijuana misdemeanor possession would be to warrant on your court date, violate probation, or go to trial
and lose. A plea bargain offer would be non-incarceratory. Diversion is probation (can be unsupervised) but you work off the conviction. That's good unless you are self-employed and don't think you'll ever care about what turns up on a background check.
As to your fiance, you could try to take the weight for both of you, but the fact that it was on her person would still make it possession, so I don't know that the prosecutor would agree to that. They certainly have the power to agree to it and to drop charges against her. But the prosecutor is the only one who could make you a deal like that. It's out of the judge's hands.
I've been able to get that for some clients of mine but not for others. It's going to depend on the facts of the case, both of your backgrounds and how eager your prosecutor would be to dispose of the case quickly. I think you'd have a better shot through a lawyer than negotiating that for yourself.
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