Kelly Rutherford, Matthew Settle, Ivanka Trump, and Jared Kushner in Gossip Girl (2007)

Kelly Rutherford, Isaac Mizrahi, and Matthew Settle in Gossip Girl (2007)

Taylor Momsen and Tim Gunn in Gossip Girl (2007)

Kelly Rutherford and Blake Lively in Gossip Girl (2007)

Kelly Rutherford, Blake Lively, and Matthew Settle in Gossip Girl (2007)

Blake Lively and Sam Page in Gossip Girl (2007)

Leighton Meester and Ed Westwick in Gossip Girl (2007)

Taylor Momsen, Leighton Meester, and Ed Westwick in Gossip Girl (2007)

Clémence Poésy and Ed Westwick in Gossip Girl (2007)

Penn Badgley and Blake Lively in Gossip Girl (2007)

Chace Crawford and Ella Rae Peck in Gossip Girl (2007)

Penn Badgley, Chace Crawford, and Ed Westwick in Gossip Girl (2007)

Penn Badgley, Blake Lively, Taylor Momsen, Leighton Meester, Jessica Szohr, Chace Crawford, and Ed Westwick in Gossip Girl (2007)

Kelly Rutherford, Penn Badgley, Blake Lively, Taylor Momsen, Matthew Settle, Leighton Meester, and Jessica Szohr in Gossip Girl (2007)

Penn Badgley, Jenny Lewis, Blake Lively, Taylor Momsen, Leighton Meester, Chace Crawford, and Ed Westwick in Gossip Girl (2007)

Penn Badgley, Blake Lively, Taylor Momsen, Leighton Meester, Chace Crawford, and Ed Westwick in Gossip Girl (2007)