Can you believe this is my 4th summer of pops?

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And since starting this series three years ago, I’m pleased to say that I have mostly had successes.


Yes, there have been some fails along the way. And those fails? All the same reason.

The damn pops would not come out of the molds.

See, I can come up with the idea, research the recipe, and execute like a boss. But there is always that moment – as I’m running the molds under the hot water – where I’m saying a silent prayer that goes something like this:

“Please, pops, come out in one piece. Please.”

And for the most part they do.

Except when they don’t.

Sometimes it’s the mix-ins – like that time I folded in roasted marshmallows for s’mores pops (these came out much better).

And sometimes it’s the ice cream – like that time I tried to make pops out of 2-ingredient no-churn.

And then SOMETIMES it’s one of the layers – like that time I made peanut butter and jelly pops and learned that jelly doesn’t freeze (they came out okay but it was touch and go and they were SUPER fragile).

So I’ve learned.

I’ve learned that 2-ingredient no-churn should be made in a loaf pan.

I’ve learned that fudge-y, caramel-y layers should be assembled in cups, not molds – so you can peel the cups away, keeping the pops intact.

Well apparently I’ve not learned enough.

Because this happened:

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Le sigh.

I’m not much of a homemade-pudding person, but I was inspired after seeing all of the pudding pops that “popped” up on Wit & Vinegar’s Popsicle Week. And then I remembered the cup-of-dirt post I did last year, which used instant pudding. And the fact that I still don’t have a kitchen (and now don’t even have a sink) sealed the deal.

So I whipped up the pudding, crushed up the Oreos, and opened up the gummy worms. I layered and packed, and layered again, and gave it all a good freeze overnight.


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Not again.

Yes again.

So I did what I always do when this happens. I cursed a lot a little, and then tasted my broken results, deciding that if the broken results tasted good I’d go back to the drawing board.

The broken results tasted good.

And fortunately I had a ton of the pudding mixture left over. So I quickly ran out and bought more Oreos and more worms and layered it all up in cups.

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Which I probably should have done in the first place, and if I’m being honest, did consider doing in the first place.

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But I thought the molds would be prettier. And I’m a sucker for prettier.

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Do you guys like pudding?

Cup of Dirt Popsicles

2 cups cold whole milk
4-ounce package instant chocolate pudding
14-ounce package Oreos, crushed into crumbs (I used a gallon-size Ziploc and a wine bottle because I can’t find the box my rolling pin is in)
8-ounce container thawed whipped topping (such as Cool Whip)
gummy worms

Whisk the milk and pudding in a large bowl; let sit for 5 minutes and fold in half the crushed Oreos and all of the whipped topping.

Spoon some of the pudding mixture into the bottoms of (12) 7-ounce cups. Smooth with the back of the spoon and sprinkle with some of the reserved Oreo crumbs. Use a clean cup to tamp down and level the mixture. Add a gummy worm. Repeat layering till cups are filled, add your popsicle sticks and freeze overnight.

To serve, use scissors to cut the cups away from the popsicles.

(print this recipe)

This delicious recipe brought to you by Sheri Silver

All the pops!

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  1. Karly on July 6, 2017 at 8:11 pm

    OMG, love these! And I’m a full grown adult! These are so much fun and perfect for hot summer days!

    • sherisilver on July 6, 2017 at 11:21 pm

      Thank you! Totally grown-up approved! đŸ™‚

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