I'm of completely no help since I've never been but I want a full trip report when you return since I'm going in November & am trying to plan similar things.
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Who do you have to probe around here to get a Chardonnay? - Roger the Alien from American Dad
you should definitely come to the drinks on Thurs. night! As for shopping, there's not really a lot in the Times Square area--most of what's there are restaurants (a lot of chains, actually) and theaters and gift shops and whatnot. There is a Sephora, though. The closest shopping area is two avenues over on fifth--in the area around Rockefeller Center (5th ave from 48-51 streets) there are a bunch of stores like Coach, BR, H&M, A/X, JCrew, Mexx, and Zara (you should check that out if you don't have one near you--it's a great store!). Then if you head north on 5th you'll run into all the fancy high-end flagship stores: Prada, Boss, LV, Tiffany, Asprey, and then Bergdorf's and Bendel. If you want to venture a little farther afield, the east village is wonderful--it's such a fun neighborhood to explore. Lots of delicious little restaurants and cool boutiques to browse in. St. Marks Place (Eighth st) is packed with inexpensive vendors of funky sunglasses, jewelry, scarves, etc.