I don't understand this transition part and what it has to do with being shy and nerdy? Skateboarding is primarily singles sport so what you do with it is totally up to you and really has nothing to with any shy or nerd as you'll be in your own world on that skateboard.
When you're in your special world, it really doesn't matter what anyone else thinks or says as its only you and you best be concentrating what you're doing then. Not there could be more here that you aren't telling us like you want to enter skateboarding because there is someone else you want to impress and being shy and nerdy, you aren't sure how but again learn how to skateboard and practice to become great and this person will notice you for sure. Just try not to show your shyness and nerdy is no big deal anymore so its up to you now. Good luck and Happy Holidays