Instead of going to the Equip screen and reequipping her with her robes put clothes on yourself and talk to her and tell her that she should put some clothes on. After you fight, she does not put her clothes back on herself. Whenever the Handmaiden teaches you more fighting moves, you both remove the clothes or armor you are wearing. Your race time will be whatever time was displayed when you crashed. Hit A and the swoop will drift forward a bit until it hits the wall.
This will bring up an option to forfeit the race. Just before you hit the wall hit the START button. Purposely direct your swoop craft into a striped barrier. This works in every swoop race except for the one on Nar Shadaa. Add a controller to the fourth port and press BLACK or WHITE to raise and lower their voice.