I was far from being a stud, but as I am also way down on the atractiveness tree, I was starting out with a handicap, so my adivce might have some value.
1. consider the first 2 dates sales calls - you are selling yourself to her. the fact that you asked her out shows that you have some interest, and your "job" is to build her interest. if you find, suring this time, or after, that you are less interested than you thought you would be, cut loose, but for the first 2 dates act like you are firmly convinced that you are interested in her.
2. objectivly wiegh what flatters you, in terms of dress, and what shows you the way you want her to percieve you. you may love to wear suits, but you are a little square and dry and you don't want her to percieve you as such, so don't wear suits, for instance. put together a "dating uniform" the best possible outfit for dates, for different types of dates. If you look really good in casual day clothes, try to set up first dates for lunch or afternoon activities, if you look great in a suit, set up dates for dinner in nice resteraunts.
3. put effort into it - reservation, nice place, wine, etc. don't scrimp
4. think about what the message you want to put across is - for instance "funny, successful guy, muscular, well traveled, carring". build up 5 or more short stories that fit each of those messages, each a little funny, none of them showing you off too clearly, or that will be a turn off, each about 2 or 3 minutes long. figure out how to fit them into conversations - so, for instance, you have 5 stories about what a sensitive guy you are, and each one has 5 diffirent ways to introduce it into a conversation, then if any one of 25 different subjects or terms is raised, you can get that message across. your job is to get those 4 or 5 messages across, while listening to her tell about herself and looking like you are riveted by her story. you want her to get home and say "my first thought was that he was a little wierd, pompous, stocky, boring and cold, but now I know that he is really funny, successful, muscular, well traveled and caring, and, on top of that, he is such a great listener"