Flint, here's my foolproof method for dating respectable chicks:
1st date: coffee, something of that nature. Spend no more than $10-20. Have a "prior engagement" limiting your time to an hour. Use your charm to show her you're an interesting, funny guy. End w a peck on the cheek, maybe the lips...alternatively, kiss her hand. If you hit it off, on to the.....
2nd date: lunch/dinner at a mid-range restaurant, bowling, arcade, drinks & dancing, something of that nature. Spend $40-50 TOPS! Spend 3-4 hours together. Go for the kiss, maybe even a lil tongue even you're feeling plucky. Finally, on to the.......
3rd date: dinner at your place, followed w a movie. Have quiche, salad and wine. Why quiche? Easy, inexpensive, exotic--but not intimidating, and you can make it for vegetarians. Also you can make it ahead of time if need be. It's better to make it in front of her though. If you don't get dick wet here, it won't ever happen. Time to move on.
Of course, based on the women you seem to patronize, a couple of 40-oz would do just as well.
BOTTOM LINE: dont ever, ever, EVER spend $100 on a woman on the first date. It reeks of desperation, isn't necessary, and if things don't work out you'll just end up kicking yourself