I've lived in Charlottesville for the past 2 years and just bought a house here. Awesome college town with excellent breweries, wineries, and restaurants.
For your nice dinner, I'd highly recommend
Tavola. Higher-end Italian fare in the Downtown Belmont neighborhood. Located a short distance away from the Downtown Mall area so still close to everything but away from the crowds and a little quieter. My favorite restaurant in Cville. Will have to make a reservation at least a week in advance.
For lunches, I'd check out
Guajiros Miami Eatery (fun cuban-style fare w/ good coffee) and
Kardinal Hall (German Pub fare w/ nice outdoor seating). You should also check out
the Dairy Market, a somewhat newish Market Hall in the center of town with different restaurants and Starr Hill Brewery connected to it.
For breakfasts, Guajiros also does a great breakfast.
Tip Top is more casual standard diner food (little outside of the downtown area).
Oakhurst Inn is a great hidden gem next to UVA that does a good brunch and has great coffee. Go to
Belle if you're into breakfast sandwiches/donuts (same neighborhood as Tavola).
Charlottesville surprisingly doesn't have the greatest bar scene. I'd personally stick to breweries like Champion, Three Notch'd, Random Row, Starr Hill, etc. Millers is a decent bar right in the Downtown Mall where you can play pool. If you want to make the 45ish-minute drive Devils Backbone is a fun outdoor brewery outside of Shenandoah. Pro Re Nata also has a similar setup in Crozet (30 minutes west just outside Shenandoah).
These are all my favorites and won't let you down!