it is a play on word. hes talking about racing for love. W for win lobby (L) for lose. he says he at the W so he has won and implying that he would consider the individual in the lobby a loss.
The ability girls and women have developed to hold several items at once in one hand. The skill has been developed due to the lack of pockets in women's clothing.
I thought she'd need multiple trips to carry her phone, keys, wallet, and Starbucks to her car since she needed the other hand to open the door, but she used her impressive girl grip to carry everything in one hand.