Maintaining the Upper West Side cafe theme, we used to frequent Cafe Mozart - for obvious reasons, she lived on the Upper West and I lived in the East Village. It's not too far from the Time Warner Center (AKA The TW Mall) where you can go see a concert or have dinner ... say at Per Se ($$$$$) - that is if you've got a little dough. Maybe a bit over the top for a first date, but if your date loves French Laundry in Napa, then this should certainly please her palate.

Now you could make the date simply at Cafe Mozart, or an after dinner walk up Broadway. If it's a day date or brunch, not too far is access to Central Park. Ahhh, a stroll through the park in late spring is magnificent. Strolling and sightseeing through CP is awesome. Pick a road or trail and avoid the zooming roller bladers. Great conversation topics can be seen or will simply emerge during the stroll.