San Francisco, CA
Firefly is one of the best places to dine in the city. Located on the edge of Noe Valley, it's a the perfect quiet spot to bring a date or an intimate guest. They have a fantastic wine selection, and have great customer service! I had the fried chicken (I know, doesn't sound very upscale) and was very pleasantly surprised. The restaurant also has great ambiance, and there is a cool ice cream parlor just up the street for desert!
Urban Outfitters has the best shopping for men's clothing in the city. They are young, fresh, in with the trends and are decently priced. They are located right downtown on Powell street, so it's easy to just pop in and peruse the store. Check them out!
PROS: Cool clothes, household items, books and games
CONS: They can be kind of pricey, depending on your budget