There are not that may cars that do not look outdated after 10 years. I know that you do not want to hear it but the DeLorean is the only one I can think of, but that comes from somebody who loves the shape of it. My wife, e.g. thinks that it is an ugly 80s car. So taste is always subjective and it is hard to find cars that do not look "out of time" in 10 years. A real classic car wouldn't, in my opinion. Something like 40s-60s cars. They are classy unless you put too much bling onto them.
And like several posters said: most women do not care about the car and I am not sure if you want to hang out with a gal that is attracted to you because of your car.
Some women like the attention a car, and therefore them, gets when driving it, but some find it embarrassing.
I would therefore not pinpoint the choice on the ladies but rather on what YOU would like to do. And YES, DeLoreans are more sausage magnets, so maybe not a good choice. But I do not even think that your second choice would be better. A classic MB (like 198 might be better, but that would increase the price and might limit your choice in the power plant.
Although on a side note: I would be interested how you would put a Volt powerplant into a DeLorean. That would call for another thread.