Well, if you're going to cook it yourself I'd recommend making it at least three times first yourself so it doesn't come out poorly. These are not "healthy" meals, just good ones. Fine for dating, not typical cuisine:

1) Homemade alfredo sauce with pasta. Alfredo sauce is very simple to make. I recommend using a blender to get a good texture. Serve with either homemade raviolis/tortellini and mushrooms (a dash of curry on the mushrooms makes for delicious flavor). If you can't get homemade see if you can buy them locally non-frozen.

2) Homemade tomato cream sauce with penne. Serve with shrimp or fresh bread (I prefer fresh bread but a lot of people feel the need for some sort of meat).

3) Shrimp scampi served with pesto linguine and tomatoes with fresh mozzarella (try to find somewhere that you can buy homemade mozzarella or fontina).

4) Shrimp bisque with homemade bread. Its vital to make the bread yourself, it needs to be fresh. I like to preface it with mussels in a white wine, lemon and pepper sauce.

In general you can go with either a white or red wine pairing. I personally like a good sangiovese or pinot grigio.