Super OT, but here we go:
General Advice: If you've heard of it (Cronuts, Magnolia, etc) it's probably a bad idea. Long lines, food usually stops being good a few months after opening because of volumes they have to produce.
Pizza - Grimaldi's is good stuff, but the line isn't worth it. John's on Bleeker is good stuff and is in the city so it's less of a hassle to get to. Most of the good stuff is in BK and not the super cool parts.
Southern - It's gone downhill a bit, but Jacob's Pickles in the UWS is good stuff. It's in my hood and we make it there reasonably often.
B. Café - Belgian. Muscles and Frites is amazing. They have a few locations
Mermaid Inn - Good seafood, good atmosphere, they have 2-3 locations around the city. Good Cocktails.
The Dutch - My go to "nice but not insane nice" place. May be hard to pick up reservations now because it's pretty popular. About 200 with drinks for two. Mind you, you are paying NYC prices. So this is unfortunately "not insane nice"
Parm - Great Italian, good atmosphere
Alder - Wylie Dufryse new joint since WD40 closed. Molecular Gastronomy stuff. I ate a Christmas tree once.
Keens Steakhouse - This is the classiest old school steak house in the city. Anyone who sends you to a tourist trap in Brooklyn doesn't know.
Eleven Madison - Suplanted Per Se as my go to insanely expensive eatery. Went here last week for my anniversary. About 750 for two with drinks.
Le Bernadin and Jean George - My go to "second tier" insanely expensive eatieres. You can get out for 400 or so if you don't do the tasting menu.
Drinks -
Classic NYC Cocktail - Monkey Bar, it's like Bemmelmen's without the cover and you don't have to listen to Woody Allen play clarinet. They typically have a nice piano playing standards on the weekends. I have a well worn path here. It's also near 5th avenue shopping (and my church, which makes it easy to pop over to if I go to evensong)
Speak Easy - I like the Little Branch and Dead Rabbit (go upstairs at the Dead Rabbit, not the bar at street level). There are a ton of good ones, Death & Co is my favorite cocktail, but hard to get into. PDT is "over" but the drinks are still good. There is a really good one in Long Island City whose name I always forget.