Ensure your cream cheese is fully softened. If it is cold, the final dip texture will be lumpy. Place the softened cream cheese into a large mixing bowl. Using an electric hand mixer or stand mixer, beat the cream cheese on medium speed for 1 to 2 minutes until it is perfectly smooth and creamy with no lumps remaining. Scrape down the sides of the bowl as needed.

Gradually add the sifted powdered sugar into the mixing bowl, one-third at a time, mixing on low speed until fully incorporated. Once all the sugar is mixed in, add the vanilla extract and the ground cinnamon (if using). Increase the mixer speed to medium-high and beat the mixture for an additional 1 minute until the dip is light and fluffy.

Pour the heavy whipping cream or whole milk into the bowl, starting with 2 tablespoons. Beat the mixture for about 30 seconds. Assess the consistency. If you desire a thinner, runnier dip, add the remaining cream/milk one teaspoon at a time until your desired dipping consistency is reached. If you prefer a thick, stand-alone frosting-like dip, use less liquid.

Cover the bowl tightly with plastic wrap, ensuring the wrap touches the surface of the dip to prevent a skin from forming. Transfer the bowl to the refrigerator and chill for at least 1 hour. Chilling allows the flavors to fully meld and ensures the dip firms up slightly, making it perfect for dipping.

Before serving, stir the dip briefly to ensure it is smooth. Transfer the Creamy Vanilla Fruit Dip to a decorative serving bowl and arrange a platter of fresh, clean, and pre-cut fruit and cookies around it. Serve immediately.