Okay, let me give you a big red flag here… This cake is so chunky and moist that it will not cut those picture-perfect slices and stand upright on your plate. BUT! Hold onto your pants, or just stretch them out, because this is probably going to be the best carrot cake you’ve had! Ever.
Grease 2 8-inch round cake pans and cover the bottoms of the pans with parchment rounds. Grease the top of the parchment. Set aside.
In a stand mixer bowl with the paddle attachment, combine the first 8 ingredients (flour through nutmeg).
Add eggs, oil, and vanilla and mix on low until combined. Add dates, walnuts, and pineapple and combine on low.
Add carrots and incorporate by hand. Divide the batter evenly into the 2 greased pans.
Bake at 350 for 45 to 50 minutes. Begin checking at 40 minutes – toothpick inserted in middle of cakes come out clean.
Cool in the pans on a rack for 20 minutes.
Loosen the cake sides by running a sharp knife between cake and sides of the pan, all the way around. Flip one cake onto a cake stand. Flip the other onto a flat plate or cooling rack. Remove parchment paper and allow to completely cool.
Once cooled, frost with Cream Cheese Frosting, or your favorite buttercream.
Cream Cheese Frosting:
In a stand mixer with paddle attachment on medium speed, whip the cream cheese to loosen and fluff up.
Add the butter and continue to blend until smooth, about 3 minutes.
Turn the mixer down to low and add the vanilla.
Keeping the mixer on low, slowly add the sifted confectioner’s sugar, one cup at a time. Once 3 cups have been added, check consistency and flavor. Add more sugar if needed.