The oldest still-operating restaurant in New York City, still in the family of the original founders. At Christmastime, it's decorated to the nines. Go with a big group: portions are large and the wine flows liberally. Look for the little buttons on the walls: in the old days, the mafia would hang out in the back room, and if diners saw the cops come in, they'd press the buttons so the mafia guys could run out the back.
Rudy's Pastry Shop is a little place my boyfriend and I like to go to on Sunday mornings. The place is super small and cozy and full of all the sweetest treats you can find. They have such a large selection of pastries and the coffee is just as delicious. The location is cute as well and a nice place to stroll afterward. There is a cute record store right around the corner.