Re: SOS! New guy needs some help.
Welcome! You seem like you have a lot on your plate already. How many girls are there? Co-worker, stripper and friends?
For your Saturday Football game, don't ask her to come ~ MAKE her come. While you're working/closing shop with her, start building that comfort/rapport, but find out a few things about her and if she's an outdoor or indoor kind of person, if she likes sports, what kind of food is her favorite, anything that will give you the upper hand for the football game and/or a day 2. Then, let her know that you're going to a football game with a few of your friends, and tell her that she should come with you because *justify a reason without neediness*.
OR give her false options: for example tell her that you're free to hang out 'this day' and 'that day.' That way, no matter which day she picks, you're still gonna see her. When she picks the day, immediately tell her specifics (ie. "Ok Saturday, [time] at [place]. Wear [color/a dress/something nice].") If she asks why, just tell her "Because I like that. :]"
But since you're closing shop with her, build some rapport and SEDUCE! Hook, Reel, Release, Repeat! How much you NEG her depends on how much she can take *only you know through observation*. Then slam her against the bar counter and bite her neck and nibble on her ear lobes.
Success or fail; everything you try can be chalked up as a learning experience~