In a small bowl, soften the unflavored gelatin in cold water and then set aside.
In a medium-sized saucepan on the stove, combine the sugar, cherry Jello and hot water. Continue stirring until everything is dissolved. Bring the jello to a boil over medium-high heat. Add in the unflavored gelatin mixture and then slowly boil on medium-low heat for 20 minutes. Remove the pot from the heat and then add in the cherry extract.
Pour the jello into a 6"x9" container that's been sprayed well with non-stick spray. I used a tupperware.
Let it stand overnight to fully chill and set.
Gently loosen the edges of the jello with your finger. Overturn the container onto a cutting board. You might have to give it a few shakes, but once one corner comes off, the whole block of jello will fall out.
Use a small 1.25" heart cookie cutter to cut 24 hearts out of the jello rectangle.
Melt chocolate in a small glass bowl for 1 minute. Let sit for 2-3 minutes, then stir until smooth. If chocolate's still chunky, place back in microwave for 15 second intervals, waiting and stirring in between intervals so that you don't seize the chocolate.
Use a fork or a Wilton Dipping Tool to dip and coat each heart in chocolate. Shake off excess chocolate and transfer to wax paper to cool and set.
Drizzle with alternating chocolate, if desired.
To coat with sugar, place 3 TBSP sugar in a bowl. Place jelly heart in bowl and spoon sugar to coat all sides.
Store candies in an airtight container on the counter or in the fridge. Will stay fresh for 7-10 days. Can be made 3-4 days in advance.