Chocolate-Dipped Strawberry Milkshakes: A Treat for Valentine’s Day!

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Celebrating Valentine’s Day in Pennsylvania can have its challenges.

Vertical image of two glasses filled with a light pink beverage garnished with assorted sprinkles and whipped cream, with text on the top and bottom of the image.

One of the biggest hurdles you’ll face during a cold February is that strawberries are terribly out of season!

When your local farms and markets are in winter hibernation mode, buying strawberries at the grocery store often leads to flavorless disappointment.

But when I am determined to serve my boo something cute, fruity, and sweet (just like him, awwwwww…) on Valentine’s Day, I have a creative way to deliver the goods.

Vertical image of two glasses filled with a creamy pink beverage garnished with chocolate, whipped cream, and sprinkles on paper with a heart print.

When I’m making this recipe for chocolate-dipped strawberry milkshakes in the dead of winter, I still need it to be intensely and unapologetically fruity.

In addition to swapping out vanilla ice cream for strawberry ice cream (or gelato, this recipe isn’t picky) I take one extra yet easy step to get maximum strawberry flavor.

Vertical image of a glass cup filled with a light pink beverage garnished with fresh fruit, whipped cream, and sprinkles.

What’s that song we would sing as kids, bullying a friend in a budding romance?

“First comes love, then comes marriage…”

When it comes to my love affair with strawberries, I say that first comes love, then comes…


Vertical image of a pink milkshake garnished with a chocolate and sprinkle rim on a white plate next to metal straws.

I like to mix a little sugar and vanilla extract with sliced fresh strawberries, then let that sit in the fridge for up to two hours.

Other than sweetening the berries, the sugar helps the fruits to release their liquids, softening the berries and creating a tasty juice, almost like a syrup.

(Speaking of syrup… you could totally use a few tablespoons of our homemade strawberry syrup as an additional ingredient to make the fruity flavor even more crazily concentrated!)

When you blend together the macerated strawberries and their juices with some ice cream and milk, you’ll get a berry delicious milkshake!

Vertical close-up image of a cup filled with a creamy pink beverage with a sprinkle rim and a whipped cream and strawberry garnish.

And there is no way I’m celebrating Valentine’s Day without chocolate. Move over just a smidge, strawberries, and share some of that glorious spotlight.

When you present this milkshake topped with whipped cream and sprinkles in a glass dipped in thick and rich chocolate, be prepared to watch your significant other gasp and swoon.

You might need to catch your breath, too!

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Horizontal image of two glasses with a creamy pink beverage garnished with whipped cream, chocolate rim, and sprinkles on a white plate.

Chocolate-Dipped Strawberry Milkshakes

  • Author: Nikki Cervone
  • Total Time: 50 minutes
  • Yield: 2 large servings (about 2 1/2 cups per serving) or 4 small servings (about 1 1/4 cups per serving) 1x


Inspired by chocolate-covered strawberries, our creamy chocolate-dipped strawberry milkshake is a playful dessert to serve on Valentine’s Day.


  • 1 pound fresh strawberries, hulled and sliced, plus more for garnish
  • 3 tablespoons granulated sugar
  • 1 teaspoon vanilla extract
  • 1/2 cup semi-sweet chocolate chips
  • 1/2 cup sprinkles, plus more for garnish
  • 1 quart (4 cups) strawberry or vanilla ice cream
  • 11 1/4 cups whole milk
  • 1/2 cup whipped cream


  1. Mix together the strawberries, granulated sugar, and vanilla extract in a bowl. Cover and place in the fridge for at least 30 minutes, or up to 2 hours. Stir halfway through the maceration process.
  2. While the strawberries are macerating, melt the chocolate chips in a heatproof bowl. Place the sprinkles in a separate shallow bowl.
  3. Dip the rims of two tall glasses into the chocolate. Before the chocolate sets, gently press the rims into the bowl of sprinkles so they stick to the chocolate. Set the glasses aside as you prepare the milkshakes.
  4. Place the strawberries and any juices they’ve released in a blender with the ice cream and 1 cup milk. Blend until smooth, about 20 to 30 seconds, using more milk if the mixture seems thick.
  5. Divide the milkshake between the prepared glasses. Top with whipped cream, and garnish with more sliced strawberries and sprinkles. Serve and enjoy immediately!
  • Prep Time: 40 minutes
  • Category: Ice Cream
  • Method: Blender
  • Cuisine: Dessert

Keywords: milkshake, strawberry, chocolate, Valentine's Day

Cooking by the Numbers…

Step 1 – Macerate the Strawberries

Hull and slice 1/2 pound of fresh strawberries, reserving a few for the final garnish on top of the whipped cream when you serve.

Horizontal image of sliced strawberries in a white bowl next to rose petals.

Mix together the strawberries, granulated sugar, and vanilla extract in a bowl. Cover and place in the fridge for at least 30 minutes, or for up to 2 hours.

The longer you let the berries macerate, the softer they will become, and the more juices they will release.

Stir about halfway through the maceration process.

Step 2 – Prep the Glasses

While the fruit is macerating, take out two glasses. You can choose any variety, like stemless wine glasses or tall parfait glasses. You want to choose glassware that can hold at least 20 ounces, or 2 1/2 cups.

Horizontal image of a hand holding an empty glass dipped in chocolate with sprinkles.

Melt the chips in a heatproof bowl. Place the sprinkles in a separate shallow bowl. Choose sprinkles that fit the holiday! These pink, red, and white nonpareils from Wilton were just the right touch of Valentine’s Day fun. Find them now on Amazon.

Instead of using melted chocolate, you can also make a homemade ganache. Prep the ganache and let it set until it reaches the desired thickness to coat the glasses. Ganache is a fun choice, especially if you love a thick drip effect on the sides of the glasses!

Make sure you choose bowls that will be able to fit the entire rim of one of your selected glasses.

Working with one glass at a time, dip the rim into the melted chocolate, and then quickly dip it into the sprinkles, before the chocolate has a chance to set completely. The sprinkles will stick to the chocolate.

Set these aside while you prepare the milkshake. You can leave them out at room temperature, or place them in the fridge if you want to use chilled glasses for serving.

Step 3 – Make the Milkshake

Measure the ice cream and whole milk, and add them to a blender. You can start with 1 cup milk and add more if the milkshake is too thick.

Horizontal image of ice cream in a blender next to a bowl of sliced red fruit.

Place the strawberries and any juices that they have released in the blender. Blend until smooth, for about 20 to 30 seconds.

Horizontal image of a pink creamy beverage in a blender.

Add the remaining milk if the mixture seems too thick, and blend again.

Step 4 – Garnish and Serve

Divide the mixture between the two prepped glasses. Top with the whipped cream, and garnish with the reserved strawberries and sprinkles.

Horizontal image of two cups filled with strawberry milkshake dipped in chocolate and sprinkles on a white plate.

Serve immediately, with straws or spoons.

Can I Use Frozen Strawberries?

Do you only have frozen strawberries available? You can use them to make this recipe!

Horizontal image of two glasses with a creamy pink beverage garnished with whipped cream, chocolate rim, and sprinkles on a white plate.

I would still macerate them, since I find that frozen strawberries often lack flavor.

Before macerating, thaw the strawberries in a strainer or colander set over a bowl in the fridge for about 4 to 5 hours. Frozen strawberries will release excess liquid that you do not want to include in your milkshake. Unlike the liquid released during maceration, the water released when defrosting frozen strawberries will water down the milkshakes.

Once thawed, continue with the maceration steps outlined in the recipe above.

You can also skip the entire maceration process by choosing to buy frozen sweetened strawberries. Defrost them for about 4 to 5 hours in the fridge before using. With this option, you can keep any juices that are released while they are defrosting.

Box of chocolates, stuffed teddy bears, romantic homemade dinners, jewelry… how do you like to shower your partner in gifts and goodies on Valentine’s Day? I think this creamy milkshake fits right in with all the other luxuries!

Let me know what you like to do for this lovey-dovey holiday in the comment section below. I might borrow some ideas from you!

For more homemade special treats to serve on Valentine’s Day, Foodal has some sweet recipes for you to try next, starting with these:

Photos by Nikki Cervone, © Ask the Experts, LLC. ALL RIGHTS RESERVED. See our TOS for more details. Originally published by Shanna Mallon on January 30, 2014. Last updated on January 13, 2022.

Nutritional information derived from a database of known generic and branded foods and ingredients and was not compiled by a registered dietitian or submitted for lab testing. It should be viewed as an approximation.

About Nikki Cervone

Nikki Cervone is an ACS Certified Cheese Professional and cheesemonger living in Pittsburgh. Nikki holds an AAS in baking/pastry from Westmoreland County Community College, a BA in Communications from Duquesne University, and an MLA in Gastronomy from Boston University. When she's not nibbling on her favorite cheeses or testing a batch of cupcakes, Nikki enjoys a healthy dose of yoga, wine, hiking, singing in the shower, and chocolate. Lots of chocolate.

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