If you're looking for a casual first date spot, Gramercy is kind of a dead zone - lots of high end hotel bars and divey pubs. Ampersand fills the void with good atmosphere (their website says: "relaxed, dimly-lit", we agree), solid drink and snack options and lots of seating.
Drink
A do-it-all drinks spot - an extensive cocktail list and solid beer and wine selections.
Eat
Bar snacks and sharable plates
Sit
Bar, hightop and table seating.