Rolo Stuffed Chocolate Chip Cookie Cups

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The year is winding down. Just a few days to go!!  I just can’t believe it. Time is flying.

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Sure, sure, I can comment on how fast Autumn is growing but the real thing that ‘gets’ me is that the show Friends has been off the air for 10 years. And that it started 20 years ago. OMG.

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That is just too much for my brain to comprehend. I mean, I still watch Friends A LOT.

I can tell you the story-line just by hearing the title of the episode... all of which start with “The One Where…”

I know random factoids about the show. I know silly little things about the cast, characters, and the show. I will kick some butt at Friends trivia. Kick butt!

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I pride myself on that fact that I can quote a lot of it. “They don’t know, we know, they know!”

Anyway, when I was making these Rolo Stuffed Chocolate Chip Cookie Cups, I remembered that Rolos are Joey’s favorite candy. Loved them so much that he ate them all over the apartment, including in his recliner, Rosita. I’m sure that he would love these babies.

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I suggest that you make these guys for a party or cookie exchange as you get a lot from a batch. 60 cookies in fact! Hey, just invite Joey Tribbiani over. He will help you eat all these cookies. Or just eat them all yourself. I don’t judge.

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These cookies are super simple to make. I actually had Autumn help me. She helped push some of the Rolos in the cookies. Aww! Anyway, the only thing that is ‘tricky’ about the cookies is that you need to wait until they are completely cooled before taking them out of the muffin tin. If you rush it the cookies will break apart or collapse in on itself. I ending up putting mine in the refrigerator for a bit so they were really cool before running my knife around them and just popping them out. I just put the chilled cookies in the microwave and nuked them for bout 15 seconds to get ooey gooey again. yum!!

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So, enjoy some of these Rolo Stuffed Chocolate Chip Cookie Cups while watching your favorite Friend’s episode.

What’s my favorite episode? ALL OF THEM!!!!!!!!

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Rolo Stuffed Chocolate Chip Cookie Cups

Makes 60 cookies


  • 2 1/4 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1 teaspoon salt
  • 1 Cup (2 sticks) butter
  • 3/4 Cup granulated sugar
  • 3/4 Cup packed brown sugar
  • 1 teaspoon vanilla extract
  • 2 large eggs
  • 1 1/2 Cups mini chocolate chips
  • 60 Rolos (you’ll need 2 12oz bags)


  1. Preheat oven to 350 degrees. Spray mini cupcake cookie tins with non-stick cooking spray.
  2. In a small bowl, combine the flour, baking soda, and salt.
  3. Beat the butter, granulated sugar, brown sugar and vanilla extract in large mixer bowl until creamy. Add the eggs, one at a time, beating well after each addition. Gradually beat in flour mixture. Stir in morsels.  
  4. Spray your hands with cooking spray. Pinch off the dough to create balls just bigger than 1″ around. Roll in your hands and drop into your cupcake tins.
  5.  Bake for 9-11 minutes, until the edges are set and golden brown. 
  6. While the cookie cups are baking, remove the wrappers off the Rolos.
  7. As soon as the cookies are out of the oven, place a Rolo in the center of each cookie cup. Let cool, you may chill in your refrigerator to speed up the process. (If you remove the cookie cups while warm they will break apart and collapse.)

Cookie dough adapted from Nestle


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