01 - In a large bowl, beat cream cheese together with granulated sugar and vanilla extract until smooth and creamy.
02 - In a separate bowl, whip the cold heavy cream until stiff peaks are formed.
03 - Gently fold whipped cream into the cream cheese mixture until thoroughly incorporated.
04 - Arrange an even layer of chocolate-striped cookies at the base of a trifle bowl or large glass dish.
05 - Spread one-third of the cream mixture over the cookies. Scatter half of the mandarin oranges and pineapple tidbits on top.
06 - Repeat layering cookies, cream mixture, and fruit, finishing with a final layer of cream.
07 - Cover with plastic wrap and refrigerate for at least 2 hours, allowing cookies to soften and flavors to meld.
08 - Before serving, decorate with reserved mandarin oranges, mini chocolate chips, and halved striped cookies.