Ryan Seacrest Pulls in Playboy Playmate 1/3/2009 11:32 AM PT Ryan Seacrest arrived in the Caribbean yesterday with 24-year-old Playboy Playmate Sara Jean Underwood. Your move, Simon Cowell. See Also Spotted: Mr. Perfect with Miss Not-So-Perfect Share on Facebook Share on X Ryan Seacrest Hook Ups Playboy Paparazzi Photo