Puree about 1 cup of diced watermelon in a blender until smooth. Strain through a fine mesh sieve to get fresh juice. Measure out 1/2 cup of juice for the cocktails.
Rim the Glass:
Rub a lemon slice around the rim of a martini glass and dip it into sugar to coat the rim.
Mix the Cocktail:
In a shaker, combine the watermelon juice, vodka, triple sec, lemon juice, and simple syrup. Fill the shaker with ice, covering the liquid.
Shake:
Shake vigorously for about 15 seconds until the mixture is well chilled.
Serve:
Strain the cocktail into the prepared martini glass. Avoid disturbing the sugared rim.
Garnish and Enjoy:
Garnish with a slice of lemon and a wedge of watermelon on the rim of the glass. Serve immediately.
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