Oh yes, the difficult dance of dating in a city like New York. Few towns have such a tight concentration of good looking, hard partying young people looking for a good time - it can be thrilling, but it can be daunting. The trick in this town is to work really hard while looking as if you're not working at all. It's a contradiction, as most things in New York are, but allow me to clarify: a gentleman must look casual and nonchalant, despite the fact he may be neither of those things. He must show up for dinner in an outfit that looks as if he carelessly threw it together on his way out of the house (even if he had planned it all week), and order dinner with a calm demeanour (even if he's been desperate for the duck confit all day). Herewith, more tips for not looking as if you are trying too hard, even when you are trying too hard.
Some Other Tips to Consider
Wear a clean shirt. Even if you prefer a vintage, worn-in look, you don't want to show up smelling like a cowboy
Lightly fragrance yourself. I've found girls uptown like the classic Polo smell (they love a preppy) and girls downtown prefer something a little muskier (because girls downtown are a little musky themselves, to be honest)
Bring a coat, even if it's warm. There's nothing more gallant than putting your coat over the shoulders of a girl during a chilly evening stroll. You won't need to throw your coat over a puddle so she can walk over it, but most ladies would agree: chivalry is not dead. And that's what will separate the men from the boys
Talk in a modern way and practise gentlemanliness in the 21st century. For example, don't ask someone "where they summer" or invite them to a "fondue party"
Be on time. A lady can be fashionably late, but her suitor cannot