Maybe if you go to certain places where it would be easier to open a conversation like an art gallery, or a dog park or the Marketplace. You could ask some woman's opinion on something and it wouldn't seem out of place if it's regarding something that's there. For example: Do you think this painting is too -fill in the blank? Then ask her what type of art does she like, etc.,etc.
I knew someone that would BORROW their friend's dog for the day just to get attention from the ladies and it definitely worked! You don't have to have your own dog to go to the dog park.