STYLETHREAD -- LET'S TALK SHOP!

Sounds like fun!  I always feel like you learn so much about someone when you vacation together.  I say go somewhere exciting neither of you have been before so you get the excitment of discovering a place together.  I like all-inclusive resorts but usually I tend to just layout on the beach and eat/drink too much when I go to those places.  Think about what you like to do together and try to plan a trip that would incorporate those activities.

I've been wanting to go to Costa Rica (never been).  I think it would be fun because you could be lazy on the beach a couple of days but get out and see the jungle, hike and do fun activities on other days.  Spring will be a good time to go and you should be able to find some deals.  I also think it would be fun to go to London or a big city together.  You get to spend time figuring out how to get around and enjoy just walking through museums or shopping and sight-seeing.

Not sure about deals, I always use my miles, and hotel points for my trips so I don't plan package deals usually.  Maybe travelocity.com?

Edited:  I just saw you live in NYC...just wanted to add you should really look into Europe.  It's usually as cheap for me to fly to London as it is to Mexico from here.  If you check travelocity you can say "flexible dates" for flights and see what month is going to have good deals for where you'd like to go.