Chocolate Chip Caramel Toffee Cookie Cups - made April 4, 2012 from The Sweet Spot blog
I finally remembered the pan I bought at Sur La Table was called a dessert cup pan. Basically, it looks like a 6-cavity muffin tin but instead of a muffin shape, there's a dome in the middle of each cavity so that when you fill it with batter or dough, bake and invert the baked product, you'll end up with a well in the center of each one. Which is perfect for something like this - a chocolate chip caramel toffee cookie cup with a nice little dip in the middle to cradle a scoop of vanilla ice cream. I used the recipe from The Sweet Spot's blog (click on the recipe title to go to the recipe) but any chocolate chip cookie recipe will do. Just let it cool for a few minutes in the pan first though before you invert or else the cookies will be too hot and could fall apart.
I like to serve these when they've been 10-12 minutes out of the oven and are still warm but not hot. It won't be too hot to melt the ice cream on contact but the caramel bits and chocolate chips will still be melt-y enough to add some gooeyness. It's not bad at room temperature either, which I discovered, all in the name of research.....after a 4-mile run at the gym (there goes that workout, haha). So yummy. And if you don't have a dessert cup pan, never fear, you can bake these in any ramekin or even muffin tins and follow the same principle. Just don't forget the ice cream.
Editing to add: since there was some interest in the dessert pan I used, here it is on amazon - Dessert Cup Pan