From 2007 to 2008, Katy dated Travie McCoy. Her song "Circle the Drain" was about their relationship. In early 2009, Katy was rumored to be dating Josh Groban, but the two never link their relationship. In 2010, Katy married Russell Brand, but they divorced in December of 2011. Also in 2012, Charlize theron dating history zimbio dated killer guitarist, Robert Ackroyd, but they flamed out quickly. In 2013, Melissa revealed that Ryan had tried to woo her while on the set, even going so far as to purchase a pricy Beluga watch once shooting wrapped! Case in point. his Two Guys, a Girl, and a Pizza Place costar Traylor Howard, who was 10 years his senior at 32 in 1998, during the first season of the show. This was before we really got to know Ryan Reynolds, and before he became the muscle-bound dude we know and love, thanks to the success he found in the 2000s. In the 1990s, though, he was still just a small-screen stud who managed to bag Traylor, who he dated for eight months!