Drop one whole vanilla wafer into the bottom of each of 6 glasses.
In a large bowl, beat the softened cream cheese on medium speed for 2 minutes until completely smooth with no lumps, scraping the bowl often.
Add the powdered sugar, vanilla, and lemon juice. Beat on low until combined, then medium for 1 minute until silky. Taste and add another tablespoon of powdered sugar if you'd like it sweeter.
In a separate cold bowl, whip the heavy cream to stiff peaks, 2 to 3 minutes.
Add the whipped cream to the cream cheese mixture in two additions, gently folding with a spatula until fully combined and no streaks remain.
Fit a piping bag with a large star or round tip (at least 1/2-inch opening). Spoon the filling in, push down toward the tip, and twist the top closed.
Pipe the filling over the wafer in each glass. Tap each glass gently on the counter to settle.
Refrigerate at least 2 hours, up to 24.
Just before serving, top each glass with crumbled vanilla wafers and fresh fruit.