If you're looking for just a fun casual place to get out of the house and spend some time just the two of you in Chapel Hill/Carrboro, this is your list. I chose these places for their casual, relaxed atmosphere, their great food and their reasonable prices. Enjoy!
Glass Half Full in Carrboro combines a congenial atmoshphere with excellent small plates and an extensive wine selection. They have a sizeable outdoor seating area that is mostly shaded. Their extensive wine list offers both 3oz and 5oz purs. In addition to the restaurant, they have an in-house wine store where you can select any bottle of wine, pay retail (not restaurant mark-up) and then just add a modest corkage fee to enjoy it with your dinner.
Acme is a local favorite. Very laid back, friendly atmosphere with an excellent and creative menu. Great cocktail choices too. Definitely don't make up your mind before you hear the specials. Small but well executed outdoor area in the back with a water feature for added ambiance.
While not technically a restaruant, I can't leave the West End Wine Bar off any date night itenerary. It is a great place to start the evening. Hang out on comfy couches and enjoy a taste or a glass of an extenive rotating list of great wine. Don't be intimidated -- the staff is friendly and knowlegeable.
4. Spice Street
If your date night is not so much about a romantic tete a tete and more about hanging out together, I recommend Spice Street on either Wednesday ($5 glasses of wine) or Thrusday (1/2 price sushi and $5 martinis) night. We never get seated indoors. We either grab an outdoor table or hop a stool at the bar and eat there. Great flat bread and tomato dipping sauce pre-meal. Easy place to share a couple different appetizers and call it a night.
I love JuJuBe. It's an smaller restaurant with a creative menu when you want a change of pace. Very lively. They define themselves as "almost Asian." On Tuesday nights, in addition to the regular menu, they offer a special tapas menu and a cocktail flight. JuJuBe is tucked away in the Glen Lennox shopping center near the intersection of 54 and 15-501.
Creative food, reasonable prices, casual atmosphere. The Granary at Fearrington just recently opened it's doors for dinner and I think it's a great date night destination. The menu is totally the creation from the head chef at the Fearrington Inn, Colin Bedford. I had a meal there recently and it was fantastic.