the chipolte girl saga continues
a cup of coffee after work >> dinner at a 5star restaurant >>>> than flaunting $100 bills in front of her and her coworkers - tossing around benjamins at chipoltes will just make you look like a douche imo - just dressing up a little and looking clean-cut, shaven, showered (ldo), etc will go much further.
how about casually handing her a note while she's handing you your change that says "Would you like to go get a cup of coffee with me after work sometime?" - don't give her chance to respond right there. While you're handing her the note say "I don't need an answer right now", take your food and go sit down. Best case she'll come over and say OK - worse case she might come over and say "thanks, but no thanks (insert lame excuse)", but in any case you'll avoid the public humiliation you fear so much.
stalking is a bad idea and is going to just weird her out by the time you muster up the balls to ask her out.