Who Has Blake Lively Dated? – Relationship Roundup! (VIDEO) Tweet June 1, 2012 by Wetpaint Entertainment Staff Related: Gossip Girl, Gossip , Relationships , Blake Lively , Penn Badgley Credit: Celebuzz We all know Blake Lively dated Penn Badgley - but who came before her Gossip Girl co-star? And who has the conservative dater (by Hollywood's standards) smooched along the way to her current beau Ryan Reynolds? Watch!