Penn Badgley got the luck because his "Gossip Girl" character, Dan Humphrey, has a kissing scene with Hilary Duff's Olivia. Several on-set pictures from the filming location at Chelsea, New York City on Wednesday, August 26 revealed Dan and Olivia hooked up before then sharing a kiss on the street.
Olivia is a movie star who is seeking a life away from the limelight by enrolling in NYU and living an "average college" life. She ends up being a roommate to Vanessa who later would link her to Dan. It is said that Dan gets in a relationship with Olivia without knowing her true identity.
"Gossip Girl" is returning on September 14 but Duff's appearance won't start until the fourth episode which is airing on October 5.
Badgley is a real-life boyfriend to co-star Blake Lively. Both have played lovers in the first season but have since gone to different directions. Lively's Serena, meanwhile, will have a romantic storyline with Sebastian Stan's Carter this season.