Most Helpful Girl
Omg I have a first date next week and I'm having the same dilemma!
It depends how fancy or how casual the restaurant is. For me, I'm probably going to wear a floral patterned dress that is more fitted in the chest/waist area but then it flares below.. its kinda short which is like because it elongates my legs. I'll wear it with wedges so I'm not uncomfortable. For you, it depends on your body type as well. If you're more curvy, you could go with something more fitted so you show off your curves. If you want something more simple but elegant, you could go with a fitted top of the dress while the lower part is loser.
(Get your dresses from Forever 21 online... cheap but cute and well-made)