Milk & Chocolate Chip Cookie Cupcakes

I was in desperate need of comfort food after the week I had. I'm a stress eater, it is not a good thing. This time I couldn't decide between chocolate chip cookies and cupcakes. So I decided that I deserved to have both! In one neat little calorie-laden package. I'm sure this idea has probably been done many times before in many different ways, but I really wanted to bake these. Chocolate chip cupcakes filled with (eggless) chocolate chip cookie dough and topped with milk icing (sweetened condensed milk icing to be exact, my favourite!) and tiny little milk bottle lollies and mini chocolate chips on top.

I couldn't resist topping them with the miniature milk and cookies. It's so damn cute! I have always had a love of miniature versions of food, whether it was mini food toys when I was young or miniature food jewellery during my teens. I still have many, many cupcake necklaces lying around. Also a waffle necklace (it smelt like maple syrup), pancake stack necklace, pie necklace, multiple doughnut earrings, chocolate covered banana slice ring, a giant mint chocolate chip ice cream scoop ring and other assorted rainbow sprinkle covered accessories that I searched high and low to find before Etsy came along. Now I'm feeling guilty because I haven't worn any of it in years, I'm totes wearing my waffle necklace tomorrow. Anyway, my point is that I love miniature food and I think it makes these cupcakes super cute. And everyone loves milk and cookies, they are meant to be together. Which reminds me, how amazing is this milk & cookies bar that I saw on Pinterest?! What the heck, I wish I could have come up with something that perfect.

These cupcakes are an adaptation of my usual foolproof cupcakes with chocolate chips, which I hollowed out the centre of and filled with cookie dough. The cookie dough filling is exactly how you want it to be, buttery, chewy and with no eggs so there's less to freak out about. To be honest you could skip the chocolate chips in the cupcake batter since there's plenty in the cookie dough filling but I like the idea of the whole cake tasting like the cookie while the icing tastes like the milk. And this icing is soooo sooooooooooooooooooooo good. I've been going on about the magic of sweetened condensed milk icing for years and I'm not going to stop anytime soon. It's very sweet and very naughty but it's so fluffy and so good with anything chocolate flavoured. If you're really worried about all the elements being too sweet together, just replace the unsalted butter with salted butter in the recipe, or add a little salt to taste. It was just the right amount of sweet for me and my cravings.

Milk & Chocolate Chip Cookie Cupcakes

(makes 12-15 cupcakes, cookie dough filling recipe from Annie's Eats)

For the cupcakes:
125g (1 stick plus about 1 tbsp) unsalted butter, at room temperature
155g (3/4 cup) sugar
2 eggs
225g (about 1 + 3/4 cups) self-raising flour + 1/4 tsp salt

1/3 cup milk
1/4 tsp vanilla extract

Optional: 1/2-2/3 cup mini semi-sweet chocolate chips (or finely chopped chocolate)

For the cookie dough filling:

55 g (4 tbsp) unsalted butter, at room temperature
6 tbsp light brown sugar, packed
1 cup plus 2 tbsp (about 135g) all-purpose flour
1/2 can (200g/7 oz) sweetened condensed milk
1/4 tsp vanilla extract

1/4 cup mini semisweet chocolate chips (or finely chopped chocolate)

For the icing:

350g (3 sticks) unsalted butter, chopped into cubes

400g (about 3 1/4 cups) icing/confectioner's sugar, sifted

1/2 can (200g/7 oz) sweetened condensed milk

To decorate: milk bottle candies, mini chocolate chip cookies

Prepare the cookie dough filling. If you want to bake the dough into the actual cupcake batter, then you will need to freeze it the night before. If you are like me and just want to hollow out your cooked cupcakes and fill them with the cookie dough filling then it only needs to be done right before baking. Place butter and sugar in a large mixing bowl and beat with an electric mixer on high until smooth and fluffy. Add flour, sweetened condensed milk and vanilla and beat again until combined. Stir in mini chocolate chips. Wrap mixture in cling film and refrigerate until it firms up a bit.

Make the chocolate chip cupcakes; Preheat oven to 180°C (350°F). Place sugar and butter in a food processor and pulse until smooth, then add milk, eggs, flour, salt and vanilla and pulse until just smooth. (If you don't have a processor, cream butter and sugar in a large mixing bowl with an electric mixer at high speed, beat in eggs one at a time and then fold juice, flour, salt into the mixture until smooth.) Stir chocolate chips into the mixture with a spatula and then spoon into a 12-hole cupcake tray lined with papers. (If you are baking frozen cookie dough into the batter, fill cases less so you end up with about 15 cupcakes and place a 2 tbsp ball of frozen cookie dough into the centre of each, I did not do it this way so no guarantees it will turn out the same!) Bake for about 20 minutes or until cupcakes are golden brown and a skewer inserted into the centre of a cupcake comes out clean. Remove from the oven and cool in tin for 5 minutes and then cool completely on a wire rack.

If you didn't bake the dough into the cakes, hollow out the centre of each cupcake using a small knife, then fill each centre with about 2 tbsp of the prepared cookie dough filling. Prepare the icing; remove the butter from the fridge about 30 mins before starting. Place butter in a large mixing bowl and beat with an electric mixer on high until smooth and fluffy, then reduce speed and gradually add icing sugar. Beat again on high until well combined. Add condensed milk and beat on high until fluffy. Place in a piping bag fitted with a 1cm round tip and pipe swirls on top of cupcakes. Use a spoon that you have heated under hot water to flatten the centre of each icing swirl. Decorate top of cupcake with milk bottle candies and mini choc chip cookies. Can be served immediately or stored in the fridge in an airtight container for several days. Remove from the fridge 30 mins before serving.