Post-trip report: Thanks guys for all the suggestions. I took some, rejected some and am saving some for later. All-in-all it was as successful a trip as it could have been considering that the weather was completely dreadful. Cold I can stand. Rainy I can stand. Windy I can stand. Cold, windy and rainy makes for a miserable combination in a city built for walking. Still and all it was a good trip. As to the details from which you guiz gave input:
FRIDAY: The first night I had made reservations at the River Cafe in Brooklyn. I don't think there could have been a better choice in the circumstance. The view, the food, the wine, the service and the company were all spectacular (the price was

). For the appetizer course, she ordered a lobster soup that was amazing and I had the fois gras two ways, which came paired with a Maison Nicolas Reserve Sauternes. The fois gras by itself was wonderful. The Sauterne by itself was fantastic. The combination of the two can only be described as a 2+2=27 event. For dinner, she ordered a fish dish (I can't remember now...it was a special) which was amazing and I ordered the lamb chops. The Sommelier was great help to us and we selected a 2002 Domaine Guy Castagnier Charmes-Chambertin Burgundy that was just sublime. I'm hard pressed to remember an overall dining experience that was better. After dinner we called the hotel concierge to ask where we should go to hear live music. Between her and the cab driver we wound up on the Lower East Side, near Delancy Street (?). We went into one place and the doorman allowed us to pop in to hear the band before paying the cover and it turned out to be a group that had clearly spent way too much time listening to Nirvana to be much interest to us (not that Nirvana isn't good, but...). We asked some of the other patrons where to go and got some directions. We wound up at the Rockwood Music Hall on Allen. The place was completely overpacked. They must have had the fire marshal on the payroll. We eventually got in and somehow my hyper-aggressive, securities lawyer girl-interest miraculously secured us a table right next to the very tiny stage. The band that night was a group called "Marwood" which we were told had been broken up for several years and this was their reunion gig. They were amazing and must have been quite popular because everyone in the place but us knew all the words to every song they played. We agreed they were fantastic and I wound up buying three of their albums off of iTunes during the show. After their set, another band played which we were told would be even better. They weren't. We stayed for part of the show then left. It was late.
SATURDAY: We slept late, then went to the gym at the hotel. The plan had been to spend the day walking the city. We had places we wanted to visit in mid-town, the Upper East Side, the Village, Chinatown, etc. Sadly for us the weather said no. We decided to try it anyway, dressed in grubby clothes and set out umbrellas in hand. She went by Ann Taylor and did some damage there then stopped in a sandwich shop for lunch. I wanted to check out a few places including Leflotts (?) in the West Village for some serious shoe damage. But by this point it was clear that this wasn't going to happen. She'd bought a ring in the diamond district on an earlier trip and had dropped it back off to have it resized. We went back by the shop, picked up the ring and she bought some earrings. By this time we were so wet and cold that there was only one thing to do...drink. So we dropped into a couple of different pubs on 47th near the hotel to compare their Nutty Irishmen. Afterward it was back to the hotel to dry off and nap through some pay-per-view movies. At some point we decided we'd need to eat dinner. She'd originally requested that we not make reservations for Saturday, but then changed her mind so we set about trying to find a place that was (a) near the hotel, but (b) not so close that we'd be tempted to walk since the weather was terrible. We wound up with reservations at Il Gattopardo across from the MoMA. While this place was certainly good, our overall impressions were probably affected by the spectacular experience the night before. Our tab here was exactly half of the night before, yet the overall experience was less than half. The food was good, not great. The wine was overpriced relative to quality and the ambiance was not what we'd hoped. I'd like to try this place again someday because perhaps we just caught them on an off night. Or perhaps we just weren't in the frame of mind to enjoy it as much. Or perhaps it just wasn't fair to eat here after the night before. Anyway... No after dinner entertainment that night. We stayed at the restaurant fairly late and then went back to the hotel. The original conception of the trip had been to do lots of walking and exploring. That simply wasn't possible given the weather this trip. We still had an amazing time and found a new favorite place in NYC. Her comment was that she enjoyed the River Cafe so much that she'd love to go back there again even over trying someplace new. Anyway...thanks for the help. Another successful SF intervention.