Beat together the cream cheese, powdered sugar, and vanilla until smooth and creamy.
Fold in the whipped topping.
Place ¼ cup of graham cracker crumbs in the bottom of each half-pint jar.
Pipe the cheesecake filling into each jar, leaving around one inch of space at the top of each jar.
Place the heart cookie cutter in the center of the jar. Carefully pipe more cheesecake mixture around the outside of the cookie cutter, then fill the inside of the cookie cutter with cherry pie filling.
Carefully lift the cookie cutter up to remove it. Continue filling the heart on top of each jar until all the jars have cherry pie filling on top.
Use a toothpick to smooth the edges of the heart, if needed.
Place the lids on the jars and chill for at least one hour before serving.
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