Start by letting your cream cheese sit at room temperature for about 30 minutes. This will make it easier to blend smoothly with the other ingredients.
In a medium mixing bowl, add the softened cream cheese and Greek yogurt. Using a hand mixer, blend until the mixture is creamy and well combined. This should take about 1-2 minutes.
Add the powdered sugar, vanilla extract, and almond extract to the cream cheese and yogurt mixture. Continue mixing until everything is well incorporated and smooth. Taste the dip; if you prefer it sweeter, feel free to add more powdered sugar to your liking.
Gently fold in the sliced cherries and dark chocolate shavings using a spatula. Be careful not to overmix; you want to maintain the beautiful pieces of fruit and chocolate throughout the dip.
Transfer the Chocolate Cherry Cheesecake Dip into a serving dish. Surround it with pretzels and graham crackers. This dip is best served immediately, but it can also be chilled in the refrigerator for a couple of hours before serving if you prefer it cold.