Enantioselective　molecular　recognition　of　chiral　molecules　that　lack　specific　interaction　sites　for　hydrogen　bonding　or　Lewis　acid–base　interactions　remains　challenging.　Here　we　introduce　the　concept　of　tailored　chiral　π-surfaces　toward　the　maximization　of　shape　complementarity.　As　we　demonstrate　for　helicenes　it　is　indeed　possible　by　pure　van-der-Waals　interactions　(π–π　interactions　and　CH–π　interactions)　to　accomplish　enantioselective　binding.　This　is　shown　for　a　novel　benzo[ghi]perylene　trisimide　(BPTI)　receptor　whose　π-scaffold　is　contorted　into　a　chiral　plane　by　functionalization　with　1,1′-bi-2-naphthol　(BINOL).　Complexation　experiments　of　enantiopure　(P)-BPTI　with　(P)-　and　(M)-[6]helicene　afforded　binding　constants　of　10　700　M−1　and　550　M−1,　respectively,　thereby　demonstrating　the　pronounced　enantiodifferentiation　by　the　homochiral　π-scaffold　of　the　BPTI　host.　The　enantioselective　recognition　is　even　observable　by　the　naked　eye　due　to　a　specific　exciplex-type　emission　originating　from　the　interacting　homochiral　π-scaffolds　of　electron-rich　[6]helicene　and　electron-poor　BPTI.　©　2022　The　Authors.　Angewandte　Chemie　International　Edition　published　by　Wiley-VCH　GmbH.