Chocolate Chip Cookie Cups

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DIY Date Night Cookie Bowl Ice Cream Sundaes

When my husband and I got engaged a friend of ours did one of those surveys where they ask us questions about each other and then the other person has to see if they get the same answer. It’s kind of like that show, The Newlywed Game – which we just so happen to have our own version of, The Not-So Newlywed Game. Anyway, one of the questions was about our favorite desserts and there was no way we were getting that one wrong because the best, ultimate, most amazingly delicious dessert of all-time is a cookie sundae. At least that’s my opinion and my husband knows better than to argue with me on sweets. The only argument that could be made against the cookie sundae is a brownie sundae but that’s a ‘fight’ for another day. Needless to say, we nailed it on the quiz, so when we came up with this sinfully delicious idea for a date night, we were both hooked—it’s a cookie cup ice cream sundae. Are you drooling yet?! We’re about to break down the exact steps you need to create this decadent dessert AND turn it into a fun date night, too!

Ice Cream Cookie Cup Sundae Date Idea

To get these Chocolate Chip Cookie Cup Sundaes going, you’ll want to print the ice cream shoppe place mats and table card that were just beautifully designed by Joanna at Cutify Creative.

After that, you’ll just need to grab a few more items:

  • Cookie Dough
  • Ice Cream
  • Muffin Pan
  • Plastic Wrap
  • Aluminum Foil
  • Place Mat Printables
  • Table Card Printable
  • Spoons

Cookie Dough

Now, let’s talk about cookie dough. I am a baker. It’s what I do. It’s what I love and I like to think I’m even a little bit known for my cookies BUT pre-made, refrigerated cookie dough is just so easy. Sometimes (ahem… today) I choose quick over homemade and it’s still wonderfully delicious. If you really want to go all out, I totally applaud you. Use your favorite cookie recipe or try this favorite from Amy at The Idea Room:

  • ¼ c. brown sugar
  • ½ c. sugar
  • 1 egg
  • ¼ c. butter
  • ¼ c. butter flavored shortening
  • 1 ⅛ c. flour
  • ½ tsp. baking powder
  • ½ tsp. salt
  • ½ tsp. vanilla
  • ¼ cup semisweet chocolate chips
  1. To make the cookie cups, beat together the shortening, butter, and sugar in a large bowl.
  2. Add the egg and vanilla extract, beating until combined.
  3. In a separate bowl, sift together the salt, baking powder, and flour, then gradually stir them into the batter. Stir in the chocolate chips.

Cookie Cups

Alrighty, got your dough? Let’s get going on turning it into cups that are perfect little ice cream bowls!

Cookie Bowl Instructions

  1. Grab your cookie dough (fresh from the tube is perfect, or you can put it into a bowl first to make it look like you toiled over it a little longer – haha!).
  2. Take out a cup (okay, okay a heaping cup) of the dough and shape it into a flat disk, and wrap it in plastic wrap. Use a rolling pin to flatten it out a bit (about 1/8-inch thick).
  3. Chill the dough in the refrigerator for at least 2 hours. Here’s a lazy girl’s hint for ya: the freezer speeds up that chill time! (While you’re waiting, it’s a good time for you to sample the remaining cookie dough, just to make sure it’s as delicious as it looks. I guess I should remind you that the raw eggs mean you shouldn’t actually eat it, but sometimes a girl just can’t help herself.)
  4. Unwrap the disk of dough. Cut out two 4-inch circles of dough. Re-roll and reuse any scraps to make additional cups (or ummm… eat the scraps… whatever floats your boat.) Another yummy option is to bake the remaining dough as cookies and then use them for topping!How to Make Ice Cream Cookie Bowls
  5. Heat the oven to 375°. Turn a regular-sized muffin tin bottom side up and cover 2 of the cup bottoms with squares of aluminum foil. Leave a cup between the ones you’re using so there’s room for rising dough! Place each one of the circular cookie dough pieces over a cup bottom, smoothing out any cracks. It’s a good idea to leave a little bit of room and not push the dough all the way to the bottom of the cup, so there’s room for the cookie to expand in the oven. (Although, a little bit of a ‘lip’ on your bowl is no problem either!)
  6. Bake the cookie cups for 10 to 12 minutes or until light brown. I’m a firm believer in under-baking cookies for soft, chewy deliciousness but you are going to want to let these get more towards the crispy side so they hold up to the ice cream!
  7. Let them cool for 10 minutes, then remove the foil and cookies together from the muffin pan. Peel off the foil and let the cups cool completely.
  8. Fill up your cookie bowls with ice cream and load on the toppings!

Date Night

Cookie Bowls for Date Night

It’s time for the main event!! The part where you not only get to eat dessert (you know, besides those little snitches of cookie dough you definitely ate while making these, or was that just me?!) but you also get to spend some quality time with the love of your life! Setting up the rest of the date is ridiculously simple.

Cookie Cup Date Night Ideas

Chocolate Chip Sundae Ice Cream Cup Place Mats

Just print out the place mats (there’s a his and hers version) that are filled with adorable conversation-coaxing games, grab a pen and get playing (and eating)!

Cookie Cup Date Night Challenges

If ice cream, cookies and cute games aren’t enough, try the challenges on the table card. The design was inspired by those old-fashioned ice cream parlors and you can simply cut a couple of slits to put it together as additional table decor. Cookie Cup Ice Cream Bowls

In true competitive fashion, the challenges on each side of the of the table card are different, so see who can complete the most! Fair warning, there’s no way you won’t laugh through these challenges.


Cookie Bowl Ice Cream Sundaes

The possibilities are seriously ENDLESS—Try different cookie dough, different ice cream flavors, add toppings, add friends and make it a cookie cup ice cream sundae bar! Please tell me you see why this is the BEST dessert ever!

Free Download

Cookie Bowl Ice Cream Sundae Date Night

Printables Designed by Joanna @ Cutify Creative Exclusively for The Dating Divas


I find a way to be highly creative and highly organized all at the same time. I love discovering a new favorite book, sitting on my back porch in the mornings, mountain views, and random science facts! I married my high school sweetheart after dating for nearly a decade and I love meeting people who know how to make me laugh, like my husband who can crack me up by just looking at me.

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Recent Comments

  1. Just wondering, how much different is this than a scoop of ice cream between two freshly baked cookies?

    1. Hi Jim E – You know, there probably isn’t a huge difference, other than you can put toppings on the ice cream in the bowl and it’s just a different way to enjoy the treat. It’s good either way, right!?

  2. How did you get yours to come away from the foil so nicely? I let mine cool and they still had to be scraped off the foil, piece by piece. Maybe its because I didn’t chill my dough for long enough? Anyway, we had vanilla ice cream with cookie crumbles on top!

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