The connection of love and chocolate is practically timeless. And while getting your chocolate in a heart-shaped box is sweet, serving it in the form of a boozy beverage is downright sexy.

In honor of the most romantic day of the year, we invited several Portland bartenders to share their recipes for chocolate-inspired cocktails you can fall in love with this Valentine’s Day. Skip the tried and true Champagne and strawberries and take the romance up a notch by whipping up one of these recipes for a sweetheart surprise, or belly up to one of these Portland-area restaurants and bars for some romance in a glass.

Photo by Aubrie LeGault

Pillow Talk at Quaintrelle

“Pillow Talk” was developed by Quaintrelle’s Bar Manager Camille Cavan in in collaboration with bartender Travis Patterson. Cavan says her approach is to always strive for balanced, approachable and seasonal cocktails. She is inspired by what works well with food, while maintaining the philosophy to keep cocktails fun and enjoyable. Bright flavors and interesting flavor combinations always make her excited. Her creative approach to drinks make us excited.

“I also stand by the ethos where creativity must come to you; you don’t find it by searching for it,” she adds. “It happens organically and if there’s too much force behind a cocktail, it loses its romanticism and often does not work.”

Makes 1 cocktail

1 1/2 ounces rye whiskey
1/2 ounce Aperol
1/4 ounce Amaro Nardini
1/4 ounce Amaro Dell’Etna
1 ounce marionberry-cacao syrup
3/4 ounce lemon juice
4 drops Crude Big Bear Coffee & Cacao bitters
1/2 ounce egg white
Garnish: spray St. Elizabeth Allspice Dram, shaved dark chocolate

Pour all ingredients into a mixing tin with ice and shake. Fine-strain the drink into a coupe and garnish with a spray of St. Elizabeth Allspice Dram and shaved dark chocolate.

Photo by Kelsey Hutchinson

The Surprise Ending at Paley’s Place

This cocktail was created by Paley’s Place bartender Charlie Gleason who says she wanted to use chocolate in a “new way” in her dessert drinks. “We’ve already seen raspberry and orange and mint as pairings,” she adds. “Bread and chocolate is a longtime favorite snack and one day, years ago, I had some lemon curd in my fridge, so I smeared some of it onto my baguette with a square of dark chocolate and was delighted with the result. That happy food memory led to this cocktail — the name comes from the unexpected combination of lemon and chocolate.”

Makes 1 cocktail

1 ounce bourbon
3/4 ounce creme de cacao
1/2 ounce Averna
1/4 ounce lemon juice
Dash vanilla extract

Pour all ingredients into a mixing tin and shake with ice. Strain and serve up.

Photo courtesy Vaux

Sumpin’ Sexy at Vaux

Vaux’s Bar Manager Joe Johnson wanted to create a fun chocolate cocktail, but strived for something new and different that wasn’t just a spiked hot chocolate or a choco-tini. This drink is equal parts funky, old school, inventive and unconventional, really fitting the bodacious bill Johnson was looking to hit.

Makes 1 cocktail

2 ounces bourbon
1 1/4 ounce clarified chocolate milk formula*
1/4 ounce Luxardo maraschino liqueur
1/4 ounce cinnamon syrup
2 dashes orange bitters
Garnish: cherry on a pick, orange peel and shaved Theo Chocolate

Stir in a mixing tin with ice. Strain into a double rocks glass with a large cube and garnish.

*To make the clarified chocolate milk formula, bring 1 quart of milk just to boil in a saucepan. Remove from the heat and whisk in 2 cups of Theo Chocolate drinking chocolate until melted and smooth. Pour in 8 ounces of lemon juice and allow to sit overnight. Strain through a cheesecloth to separate most of the curd. You now have chocolate ricotta to play with.  Strain the whey through a coffee filter slowly.  This will probably take 8 hours. The now clear whey is your clarified chocolate milk “formula.”

Photo by Dylan + Jeni

The Grasshopper at Pepe le Moko

According to Jeffrey Morgenthaler, bar manager at Clyde Common and Pepe Le Moko, the classic Grasshopper is traditionally comprised of equal parts creme de cacao, creme de menthe and cream. “Our version at Pepe Le Moko is a tribute to the Midwest blended ice cream version, updated with a little Fernet Branca and local sea salt,” he adds.

Makes 1 cocktail

1 1/2 ounces green crème de menthe
1 1/2 ounces white crème de cacao
1 ounce half and half
1 teaspoon Fernet Branca
1 pinch Jacobsen Sea Salt
1/2 cup vanilla ice cream
1 cup crushed ice
Garnish: mint sprig

Combine all ingredients in a blender and blend until smooth. Pour into a frosted glass and garnish with a mint sprig.