The one time I requested tickets for the Late Show, they called me back and asked me one trivia question: "Where is Paul Shaffer from?" I panicked 'cause I forgot for a moment, then remembered that he was from Canada. I stalled and said, "Well I know Dave is from Indiana. I even know he used to be a weatherman there! But Paul....Oh yeah! He's from Canada! I dunno which province though. Do I hafta know that?" I didn't so I got the tix. Phew!
It was also cool 'cause the date I requested was my birthday 3 years ago. Woohoo!
As for restaurants, there are so many good ones in New York. To recommend one, it would depend on how much you're willing to spend (up to $100 for 2?) and cuisine. I would recommend Nobu 'cause I think the chef there is one of the Iron Chefs; the Japanese food there is amazing; and I heard it's co-owned by Robert De Niro.
These sites have pretty good suggestions and lists according to cuisine and popularity, etc.
Citysearch
Zagat