Flourless Chocolate-Date Cake

In a small saucepan over medium-low heat, bring dates and bourbon to a simmer; cook, stirring, until almost all of liquid is absorbed. Remove from heat; cover and let cool. Purée in a food processor until smooth. (You should have about 1 cup.)

Preheat oven to 325°F. Butter a 9-inch springform pan. Line bottom with parchment; butter parchment. Dust pan with cocoa, tapping out any excess.

In a heatproof bowl set over (not in) a pan of simmering water, melt butter and chocolate, whisking until smooth. Remove from heat. Whisk in 2/3 cup date purée. Let cool; whisk in egg yolks, kosher salt, and cinnamon.

Beat egg whites on medium-high speed until soft peaks form, about 2 minutes. Slowly add 1/4 cup sugar, beating until stiff glossy peaks form. Fold one-third of whites into chocolate mixture, then fold in remaining whites. Transfer to prepared pan, smoothing top with an offset spatula.

Bake until set, cracking a bit on edges, and shiny in center, about 30 minutes. Transfer pan to a wire rack and let cool completely. Run a paring knife around sides of pan; remove from pan and transfer to a cake plate.

In a small saucepan over medium-high heat, bring remaining 1 cup sugar and 1/4 cup water to a boil, stirring until sugar is dissolved. Let boil, without stirring, until deep golden brown, swirling pan to color evenly, and washing down sides of pan with a wet pastry brush to keep crystals from forming, 10 to 11 minutes. Remove from heat; carefully pour in cream (it will spatter), stirring to combine. Stir in remaining 1/3 cup date purée. Pass caramel through a fine sieve to remove lumps. Let cool until thick but pourable, about 30 minutes.

Pour caramel over cake, spreading with an offset spatula so it drips over sides. Sprinkle with flaky salt. Slice cake with a knife dipped in hot water, then wiped down between slices; serve with whipped cream.