Sadie Hawkins Sling

Sadie Hawkins Sling
  • Yield:2
  • Active time:10 minutes
  • Total time:overnight

[Photograph: Jessica Leibowitz]

You'll have to ask someone to share this one with you—it's definitely big enough for two people. As silly as it looks, served in a pineapple with bendy straws, this cocktail from JBird in New York is a serious drink, refreshing but spicy and complex.


  • 1 pineapple
  • To make demerara syrup
  • 1 cup demerara sugar
  • 1/2 cup water
  • Ice
  • 2 dashes Bittermen's Tiki bitters
  • 1/2 ounce demerara syrup
  • 3/4 ounce John D. Taylor's Falernum
  • 3/4 ounce pear brandy
  • 1/2 ounce Rothman & Winter Orchard Apricot Liqueur
  • 1 ounce freshly squeezed lemon juice
  • 2 ounces pineapple juice
  • 4 ounces Buffalo Trace Bourbon
  • Crushed Ice
  • Garnish: pineapple leaves, orange slices, bendy straws, umbrella


  1. 1.

    Core pineapple (leaving a few inches of fruit at the bottom to make an oversize vessel.) Freeze overnight in a Ziploc bag.

  2. 2.

    To make demerara syrup: heat sugar with water over low in a small saucepan, stirring to dissolve. Let cool. Keep refrigerated.

  3. 3.

    To make cocktail: Put a small amount of ice in a cocktail shaker, add bitters, demerara syrup, falernum, pear brandy, apricot liqueur, lemon juice, pineapple juice, and bourbon. Shake and strain into the cored and frozen pineapple. Add crushed ice, stir with a swizzle stick or long spoon. Add more crushed ice, garnish as desired.

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