OK, I'm just gonna put this out there: Chocolate wine exists. And, it's actually pretty affordable. Not like $5 Target wine affordable, but like, I can buy a bottle and still order pizza affordable.
According to Delish, the UK based alcohol company, Rubis, is selling the sweet (and awesome!) beverage for roughly $15 at The Drink Shop or The Whiskey Exchange, and it's featured in Aldi's 2017 wine advent calendar. The only kicker is, since it ships from the UK, the shipping cost to the US is around $40... ugh. Yeah, if you're not in the UK, maybe put your pizza delivery on hold and break out the instant ramen.
According to Rubis' website, the wine is a blend of tempranillo wine and chocolate flavor, with "notes of rich cherry and red fruit enveloped in velvety premium dark chocolate."
They recommend a glass after dinner or for any special occasion, but I say to heck with that! Enjoy it whenever, with whatever you want. I imagine it would go best with desserts, but how about with a nice cheese plate to pregame dinner? I love cheese plates...
Anyways, chocolate wine is a thing, and although I haven't got to try it yet, I'm banking on this being way better than a shot of Pinnacle Whipped or any other dessert-themed liqueurs. I mean, it's also wine. Wine always wins.