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I have always straddled the bike first, up-righted it off the side stand, & while holding it there my wife would get on.
That's generally how it's done... except
My OL has an ailment that requires her to climb onto the left passenger floorboard (with it on the jiffy stand) and I lift and move her right foot up and over the seat, then get on. I just do whatever it takes. I've left her on the bike with it on the stand but man, that makes me nervous.
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