k dude, lately i've been failing in the club scene, but one thing that im awesome at is gaming at work. you have to realize that you are in a position of power at work, but you are also in a position of weakness cuz she controls your job, but she must never know that. all you have to do is tone your game down to where if your grandma was listening to it she would just smirk, instead of slap you in the head for being inappropriate. you can always save the inapproriate material for later, perhaps day 2 or first time hanging out. heres what i do... im a male flight attendant and i love my job, theres always another chance for another girl on the very next flight! one thing i do is incorporate some playful teasing example:
"what are you so (mad/happy) about?"
(when you go to hand her things, pull it back as she goes to grab for it. i notice that this works best when you dont look at her for a reaction and look away with a smile on your face. then when she goes to grab it again pull it away again and tell her, aww not even my 6 yr old cousin falls for that trick! she will begin to realize that your making a fool of her and get all pouty then you say "all you had to do was ask politely" and she'll comply and say please, then give her the item and then immediately run an opener works like a charm!)
(if you work at a high priced store) say with a BIG smile on your face "those (shoes/that purse/shirt) is nice...you know knockoffs are coming closer to the real thing these days...
(as your taking her clothes to a dressing room, or if she is asking your opinion dont be afraid to come off a lil gay and give her a sincere suggestion for how to look better. frame it like this)
HB: here's my clothes, i would like to get a dressing room
You: (look at clothes, look at her with a coy smile on your face) you sure? ok... you know (some other fashion) has been popular lately, i think you could manage to pull it off (girls are all about what is popular, thats why preselection works so well, because what other women find valuable must be valuable for them too.) then when she puts it on, smile and laugh and say, wow im good, you know i used to date a fashion stylist (then run style's jealous girlfriend, this opener is gold for this)
OR
HB: hey do you think this looks good on me?
You: Ehh... (go grab a scarf or a cool hat or something then put it on her and tilt it to the side or something and then say) Ok There we go! now you look almost cool enough to hang around me! look away and pretend to walk off. then turn your head and say "sucks im gay, otherwise we'd be such a cute couple...
One example of how i run game at work is this...
Me: You want anything to drink?
HB:sprite
Me: we're all out. (with a smile on my face)
HB:ok...coke
Me: all out.
HB: haha k well what do you have?!
Me: well we have whatever you want, but where i come from we use manners when we want something

(i usually get a bunch of IOI's at this point and then what happens next is i make her pass out peanuts and embarass her by introducing her as thing 1 over the loud speaker. works like a charm, but once again this is only one weapon combo in my arsenal)
hopefully my advice worked! keep gaming
and oh yeah...have fun.