Penn badgley and blake lively dating
Unfortunately, though, those relationships don’t always work out (see both examples above), which can make things super awkward if your on-screen characters are still very much together.
That was also the case for “Gossip Girl” stars Penn Badgley and Blake Lively, who dated on and off from 2007 to 2010 — a time that overlapped with their characters’ on-screen relationship.
While appearing on Bravo’s “Watch What Happens Live,” the 28-year-old “Cymbeline” star was asked about his best on-screen kiss. In our opinion, though, Penn’s admission is actually kind of a compliment to Blake.shot Blake Lively into superstardom and Leonardo Di Caprio was, well, Leonardo Di Caprio. She was documenting her life in photographs in a way that people were not yet doing. But now we've gotten a small look into their relationship from Lively's co-workers who witnessed a lot of it, and guys, this might be the funniest thing you'll read all week. episodes, Blake was dating [Di Caprio] at the time, and she had this thing where she had a doll that she took photos of that she sent to Leo. "She was on a date with another guy, and I was on a date with another girl," Ryan recalled."That was the most awkward date [from their perspective] probably because we were just like fireworks coming across." And the rest is history!