Toss the diced strawberries with 1 tablespoon of sugar in a medium bowl. Set aside to macerate.
Add the graham crackers to the bowl of a food processor and pulse until they become crumbs. You should have around 1 1/2 cups of graham cracker crumbs. (see note)
Mix the graham cracker crumbs with the melted butter and 1/4 cup sugar in a mixing bowl until evenly moistened and well combined. Set aside.
With a hand mixture, beat the cream cheese in a large mixing bowl until light and fluffy. Add in the Cool Whip and vanilla and mix until combined.
Spoon half of the graham cracker mixture evenly into the bottom of each mason jar. Divide half of the strawberries between the jar. Divide half of the cream cheese mixture between the jars. Repeat these layers, in the same order, with the remaining ingredients.
Top each parfait with a dollop of whipped cream and two strawberry halves. Serve immediately. (If you're serving the parfaits later, chill them in the fridge and wait to add the garnish on top until just before serving.)
Notes
If you don't have a food processor, you can place the graham crackers into a large Ziploc bag and seal it. Then use a rolling pin to smash the crackers into fine crumbs.