Is it just me or is this kid just trying to impress us with how much money he supposedly has or how hot the chick he's supposedly dating is?
My girlfriend and I have never really been on a date. At least, we don't call them dates. We just hang out. It's about being together and occasionally doing something fun. It's about having a really good friend that you can mess around with
And while I think the both of us dress nice, we never dress pretentiously, and we took a limo to PROM, but not to lunch or a mall. We take the subway or a taxi or one of our drivers take us (this is not contradictory, having a driver in China is very very common, and pretty inexpensive).
If you're for real, and this girl is too, and you're serious about what you're planning...
then you're an enormous tool. Seriously.
Find a girl who won't judge you for how much of a fashionista you are or how much money you have. If you go out with this girl, then you're doing it for purely superficial reasons, and I'm sorry, but that makes you an idiot. When you're older, you can look for NSA tail and casual relationships, but right now, you're in way over your head.
I say this because like mentioned before, I'm assuming you can't drive and/or aren't out of highschool yet.
Grow up, man.