Does Chocolate Really Pair Well with Wine?

Not necessarily.

If you think about it chocolate with Cabs, Zins and Pinot is not a good pairing. The tannins in wine do not play nicely with the bitterness of chocolate. You’d be better off saving that chocolate for sweeter wine like a Port, late harvest or red dessert wines. Another option is Lambrusco, the Italian sparkling red wine which is also slightly sweet. Give it a try and see if you agree.