There's an Art Walk in the Arts District every Thursday night in the fall between 7 and 9 p.m. There's local artists, live music, and a great vibe that can't be beat. Marshall Way Arts District runs from Indian School Rd. to 5th Ave. in the Downtown area of Scottsdale.
The Casablanca Lounge has an awesome rooftop bar and does some great live music on some nights. The classy vibe is a few steps above the college crowd, so that shouldn't be an issue. Jade Bar and the Living Room are also trendy spots that you should check out.
Flemming's Prime Steakhouse & Wne Bar on N. Scottsdale Rd. is my favorite. Nothing better than seeing an entire wine list on an iPad in front of you-- that's luxury. Not to mention, their steaks are mouthwatering. Mastro's City Hall is also good, as well as Donovan's.