He has also acted in the films such as Greetings from Tim Buckley (2013), Penn appeared as Young Sean in the 2001 American independent film The Fluffer.Penn guest appeared in an American television sitcom, Will & Grace in 1999 for his role as Todd in an episode titled ” Never Promised You an Olive Garden”.Da han i 2008 ble kjæreste med motspilleren Blake Lively (29), som hadde hovedrollen som Serena van der Woodsen i tv-serien, ble det mye oppmerksomhet rundt romansen. Etter bruddet med Blake innledet Penn et forhold til Zoë Kravitz (28) - datter av artisten Lenny Kravitz (52).Etter nesten to år sammen tok også kjærligheten mellom dem slutt, og siden 2014 har kjekkasen vært kjæreste med Domino Kirke.
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