Friends don’t let friends pair chocolate and red wine.
The problem is that any food/wine pairing depends on balancing the sweetness of the wine with the sweetness of the food. If the food is sweeter than the wine, the wine will taste dull and acidic. If the wine is much sweeter than the food, the food will taste flat and uninteresting. It is devilishly difficult to get this balance right with chocolate and wine.
Furthermore, quality dark chocolate has bitter notes and pairing it with any tannic wine will be pairing bitter with bitter—usually that will just be too bitter!
I have on occasion had a red wine that works with chocolate but very seldom and it is impossible to predict when it will work. (A milk chocolate/Merlot pairing has the best odds, but it’s still a crap shoot)
Are there some wines that pair with chocolate? Sure. Port, Banyuls, and Pedro Jimenez Sherry are some of favorites. Sometimes a Riesling gets it right. These are primarily dessert wines. If you must pair, stick with them.
The idea of chocolate and wine on Valentine’s Day is primarily marketing hype by people who want to sell both.
If you want to spark the romance, have the wine with dinner and chase the chocolate with something a little sweeter—use your imagination.