Planning a first date is like fixing dinner for two. Plan it out in phases. And make 3 phase plan with back up plans.
And also every woman/girl is diffrent. If you can be friends with her friends this will give you privy access to info that you want/need to know. Be sly about it and dont ask questions directly to get the anwsers you need. Like ask her friends what songs they have/would put on a playlist(take this info with a pinch of salt and compensate lace in your personality too, because her friends will talk to her about you if you talk to them and vice versa COUNT ON THIS ).
Phase1) Think about what you know about this person. Talk about it over dinner or a walk in the park. ( this lets you both get to know each other.... dont address awkward topics unless she brings it up.)
Phase two) If she likes to be active, Procede to the park or go ride go karts, something that will be entertaining to the both of you but isnt exclusive. back up plan if she likes to kick back or is a drama queen(likes theater/movies this is found out from cleverly asking questions and deducing from phase 1) Go to a community production or a movie.(since this is your first date dont try the lame yawn/ arm around her shoulder... its hokey.. and a little strong. Id go with a movie before it gets dark. Or finishes shortly after.
Phase 3) the closing end with a sweet note...example... coffee/tea/ Ice cream/ slurpies from 7-11(if your paying for it and are on a budget make it classy go to the least ghetto 711 you know lol).
If your driving make a really varried play list. I'm sure you have room on your 8gig or more Ipod to show her you have taste in music.... put in the spooge that is currently playing on the local top 40 station. (this shows her your considerate and can have a open mind about things, even if you dont really like it, and she does)
Things you do and dont do totally reflect your mentality, and cognative capacity. She'll rember things you do and dont do and discuss them with all of her friends so even if things dont work out with her dont act like or be a douche, maybe her friend is a better match for you and is cute to boot.
Good luck, think, plan, and be confident. Being cool isnt about trying to be cool, its about being and accepting who you are and being true to your self and those around you.