In Manhattan there is a great Italian restaurant called Becco in the theatre district.
They have an extensive wine list and majority of their wine bottles go for $25. It's more value than buying by the glass. They have a regular menu or you can choose their pasta special which includes 3 different types of pasta. This is what I chose. It was delicious. The pasta was fresh and it was cooked correctly, al dente! The waiters come around and ask you if you want seconds.
For dessert, instead of buying individual desserts they also have a dessert sampler. This I highly recommend!!