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 17 of 18 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 17 Jessica Szohr Then Szohr played Dan Humphrey's childhood best friend, Vanessa, on "Gossip Girl." She was 22 when she took on the role. Previous Next Start Slideshow MoviesPenn BadgleyGossip GirlLeighton MeesterBlake LivelyTV