Preheat your oven to 300°F.
Slice the dates lengthwise down the center and remove the pit.
Stuff each date with a cherry. Make sure that the sides of the date wrap all around the cherry; mold the date to stick together if necessary so the cherry has a secure "boat."
Pop those babies in the oven for about 7 minutes if using fresh cherries, or 10 minutes if using frozen.
While the dates are in the oven, melt your chocolate in the microwave or on the stovetop using a double boiler method.
Remove the dates from the oven and let cool until they're not too hot to touch.
Using a fork (or other preferred instrument) dip/coat the dates in the melted chocolate and set on a parchment paper-lined tray. Pop the tray in the freezer for about an hour (or until the chocolate hardens), and you're ready to serve!
Give these delicious treats to your Valentine, or store them in your fridge until they're all gobbled up.