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dotn even ask her, just go for it. and if she says she doesnt want to, she is just playing hard to get and in that case you have to force yourself on her
kill her, a dead girl cant snitch, cut her into little bits, it makes it easier to hide, dige the holes twice as deep as you feel satisfactory YOU CANT BLOW THIS
I'd say start with boxes if your not already.
practice your ollies at other parts of the hill, if its absolutely nesiscary that you need to ollie onto the rail. otherwise you should just be able to have enough speed to get on. (it all just depends on the situation)
maybe practice turning sideways more and more.. example: start by going 50 50 (straight on), next time, turn sideways a little more, and so on. As you turn sideways, have a decently wide stance, probably about shoulder width.
Sorry for dub post, but OP you should practice riding switch, then whenever you get on a box or rail focus on coming on straight and landing switch. When people don't do that when learning, they end up zeaching (going less than 90 degrees) all the time and never learn to grind well. Start with ride on boxes, come up the lip and as soon as your tips touch the box surface, turn 90 degrees. And focus on riding off switch, and it should all come around.