Double Booking

I have two dates tomorrow. For a girl who didn't get out all that much last year this is an exciting phenomenon- one my Dude Friends tell me is something to be proud of.
Ok I'll be proud.
I do on the other hand feel a bit like a date slut.
Luckily they are both at similar venues so I don't have to cart around another set of clothing- could you imagine me attempting to change in my car while driving a stick shift down Van Ness? Stockings flying, jacket wedged at the elbows behind my back, holding the steering wheel with my teeth while attempting to wiggle out of a pair of jeans? (I may bring another pair of shoes because I'm that girl but shoes don't really count). And while I don't have to worry about a costume change, they are at opposite ends of town. If date 3 lasts more than 2.5hrs I'm going to be late to date 4. Timing it seems, could be problematic. And how do you subtly check your clock to see what time it is? Or do you say at the beginning that you are going to have to leave at O-dark-Thirty? It seems either one of those options would set an uncomfortable tone.
The other issue is that both dates are at bars. Fantastic. I get to show up to date 4 smelling like stale beer- nothing says "I'm a classy girl you might like to get to know better" like the sent of Dive Bar.