Okay so—hear me out—I once tried to make a Pineapple RumChata Shortcakes in a dorm room microwave using a plastic bowl, boxed mix, and what I thought was brown sugar (spoiler: it was instant coffee granules).
Yeah. That thing looked like it came out of a crime scene on CSI: Miami.

Fast-forward a few (okay, many) years and now I have a grown-up version that actually tastes like something you’d want to put in your mouth: Pineapple RumChata Shortcakes.
It’s tropical, it’s boozy, it’s messy in all the best ways—and yes, there’s whipped cream. Buckets of it, if you do it right.

This recipe? It’s for when you’re feeling like a vacation but your PTO is trapped under a pile of meetings and you’re emotionally too fragile for TSA lines. You ever been there?

So what even is a Pineapple RumChata Shortcake?

Glad you asked.
Imagine this:

  • Flaky, buttery shortcakes that almost make you cry happy tears
  • Pineapple chunks, slightly caramelized in butter and brown sugar (don’t worry, I know the difference now)
  • A generous drizzle—okay fine, a full-on pour—of RumChata
  • Clouds of whipped cream
  • Maybe a cherry on top if you’re feelin’ flirty

It’s like if a tropical cocktail and a grandma’s biscuit had a fling in the summer of ’06 and accidentally invented dessert gold.

Where This Glorious Mess Came From

You know those Pinterest-perfect recipes where everything is beige and beautiful and you just know that person never breaks a sweat? This is not that.

This recipe was born on a sticky July night when I had a half-empty bottle of RumChata, a can of pineapple that expired probably recently, and zero motivation to turn on the oven. And yet—magic. Or like…alcohol-fueled perseverance.

The first version? A disaster. I accidentally used garlic powder instead of sugar. (Why do we even let spice jars look so similar??)
But the second try? Pure joy. Like…standing-in-front-of-the-fridge-eating-it-with-a-fork-at-midnight joy.

Ingredients You’ll Probably Have to Hunt Down (but WORTH IT)

For the shortcakes:

  • 2 cups all-purpose flour
  • 1 tbsp baking powder
  • 1/4 tsp salt
  • 1/2 cup cold unsalted butter (cut into cubes)
  • 3/4 cup heavy cream
  • 2 tbsp sugar (the sweet kind, not garlic powder)
  • 1 tsp vanilla

pineapple boozy filling:

  • 1 1/2 cups pineapple chunks (fresh, canned, or whatever’s left from your last piña colada phase)
  • 2 tbsp brown sugar
  • 1 tbsp butter
  • 1/4 cup RumChata (plus more for drizzling)

whipped topping:

  • 1 cup heavy whipping cream
  • 2 tbsp powdered sugar
  • 1 tsp vanilla extract
  • Optional: a dash of cinnamon or a splash of RumChata because we’re rebels

Making It: Like a Tropical Bake-Off Without the Judgment

Let’s Make Shortcakes That Won’t Shatter Your Soul

Okay, you’ll mix the dry stuff (flour, baking powder, salt, sugar) in a bowl.
Cut in that cold butter with a pastry cutter or two forks—whatever feels emotionally right. You want crumbly, sandy texture—not like wet Play-Doh.
Add the cream and vanilla, stir until it’s just barely holding together. No overmixing or the Shortcake Gods will curse you.

Plop dough blobs (yes, that’s the technical term) onto a baking sheet. Bake at 425°F for 12–14 minutes until golden, puffy, and glorious. Let ’em cool or they’ll melt the whipped cream into sadness.

Pineapple RumChata Lovefest

Melt butter in a pan. Toss in pineapple and brown sugar. Stir around until it gets glossy and golden and smells like summer break in your mouth.

Now remove from heat and pour in the RumChata—unless you like surprise flambés. Stir and set aside. Taste-test a piece or three. For quality control. Obviously.

Whip It Good

Chill your bowl and beaters if you’re feeling fancy (or if your AC’s broken). Beat the cream, sugar, and vanilla until soft peaks form. Add RumChata or cinnamon if you want to feel spicy.

Assemble the Beautiful Mess

Slice your shortcakes in half like a biscuit sandwich. Layer pineapple + whipped cream + a drizzle of extra RumChata. Top with the other half. More cream? Sure. Cherry? Live your best life.

Serving Suggestion:

Right after you finish yelling “WHY IS THIS SO GOOD?” at no one in particular, I recommend eating these:

  • On the patio with friends and cheap paper plates
  • As a post-breakup pick-me-up (add extra RumChata, no judgment)
  • While binge-watching something dumb and comforting (cue Golden Girls reruns)
  • Or literally in bed, because we’re adults now and no one can stop us

What If You Don’t Have RumChata?

That’s like saying, “What if I don’t have joy?”
But okay—sub in Bailey’s, coconut milk + cinnamon, or spiced rum and a splash of cream. Not exactly the same, but hey, we make do.

Mistakes I Made So You Don’t Have To:

  • DO NOT confuse garlic powder for sugar again. Seriously.
  • Don’t skip cooling the shortcakes—unless you enjoy whipped soup.
  • Do NOT attempt to flambé the RumChata. (Ask me how I know.)

Would I Make These Again?

Um. Yes. I made them again the day after writing this post. And again for my cousin’s weird potluck brunch. And again when my friend broke up with her situationship (she cried into the whipped cream, it was poetic).

These Pineapple RumChata Shortcakes? They’re my chaotic, boozy love language now.

Bonus Chaos Idea: Make It a Trifle

Layer everything in a big bowl like a dessert lasagna. Bonus points if you eat it with a serving spoon straight from the dish like you’re in a rom-com montage.

Final Thoughts (or whatever’s left in my brain at this point)

This dessert doesn’t care if you burned the dinner. It doesn’t care if your whipped cream looks like a failed cloud. It shows up anyway. Sweet. Messy. Slightly tipsy. Just like the best kind of friend.

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