Popsugar Celebrity Ashley Benson Cara Delevingne and Ashley Benson's Relationship Timeline The Complete Timeline of Cara Delevingne and Ashley Benson's Relationship 20 December 2019 by Amanda Prahl View On One Page Photo 9 of 11 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 9 Sept. 2019: Cara and Ashley Snuggle Up at the US Open Ashley and Cara shared a smooch as they cheered on the competitors at the 2019 US Open. Previous Next Start Slideshow Ashley BensonCelebrity CouplesCara Delevingne