Popsugar Entertainment Movies The Cast of Gossip Girl Then vs. Now What the Cast of "Gossip Girl" Have Been Up to Since the Show Ended 7 November 2023 by Eden Arielle Gordon View On One Page Photo 3 of 18 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 3 Penn Badgley Then Badgley was 20 when "Gossip Girl" started, and he had a romance with his onscreen crush, Lively, between 2007 and 2010. Previous Next Start Slideshow MoviesPenn BadgleyGossip GirlLeighton MeesterBlake LivelyTV