All things considered, including a man absolutely hating on his date for the evening, when it comes to the departure, a gentleman (or a boy with half a brain) first makes sure his date gets into her cab before he bounces into his respective subway, at the very least.
My personal rule of thumb is that the man actually get into the cab with his date, drop her off, and then head home. OR pay for his date’s cab home. OR walk his date home if the location is convenient. But at the very least… put her into the cab first before you head home!
Do NOT hug her awkwardly outside of your subway station and bid her addieu before she’s even had a chance to flag down a car. Men of New York, this is rude behavior, and I honestly wonder what your mother would say if she knew you treated women this way.
It doesn’t really matter if there is no chemistry. If you lived in any other city or town in America, you would have probably picked her up with your car and drove her home after. Just because you have a MetroCard in your pocket doesn’t mean that chivalry goes out the window.