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For me it was my second season.
You should feel confident in your ability to handle the bike before you even think about taking someone else's life into your hands. Everything that is unstable about a motorcycle is amplified by carrying a passenger. They're wobbly whenever the passenger moves around, and low speed maneuvers are even more nerve-wracking. Not to mention, the extra weight is very obvious in your braking ability and your handling.
Start small. Take a passenger for a little trip around the neighborhood. Practice starts and stops, and make a point to be smooth and careful. The bike will feel completely new with a passenger on back. Make sure both you and your passenger are comfortable before you make it out of the neighborhood and onto faster roads.
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