Did you say free wine & chocolate? One of our favorite wine spots in downtown Dallas is Grill & Vine at the Westin on Elm Street (you can access from Main Street as well). They have a great wine by the glass list, hand-crafted cocktails and items like flatbreads and entrees including Sweet Tea Brined Chicken Breast and Porcini Ravioli. For a hotel restaurant they are also priced extremely reasonably.
On Fridays they have live music from 6-9pm which is typically acoustic guitar and singing. And on Tuesdays they have a pairing that's free. Their chef chooses a small plate and pairs it with either a beer, cocktail or wine. And it's free.
This coming Wednesday they are doing a complimentary JLohr Vineyards event with live music and chocolate. From 5:30-7p meet with a rep from JLohr and sample 3 wines with chocolate while listening to live music.
Now THAT's something worth putting on your calendar! And if you haven't been to Grill & Vine stop on in and enjoy! I still say they have one of the best views in downtown Dallas even though it's only on the 2nd floor.