Josh reportedly started dating actress January Jones, famous for her role in television show, Mad Men and for doing quite a few roles in films like X-Men: the Last Stand. They got hooked-up and while Josh was the sixth boyfriend of Jones, it was Josh’ first time in an official relationship. They supposedly met at some public event and are said to have been very close since the first meet itself. The media came to know of the affair somewhere around, in August 2003 and the two publicly anticipated their relationship. Given the clean image, Josh had and the ironically scarred image January possessed, gossip circles started talking about how the relationship would never quite work. But it did not quite happen and the two seemed to go well and smooth, with both their professional and personal lives before they suddenly decided to break-up in June 2006, hence ending a three year old relation. Their representatives had, and then stated that they were taking a break but after a long gap with no news of a patch-up, it was clear that everything was over, forever.

Josh was next, linked up with star celebrity and twitter queen, Katy Perry in March 2009, when the proximity between the two seemed to be rising. Although, Perry was supposedly dating John Mayer back then, it was only good news for the paparazzi after both had publicly appreciated each other and quite a few fans were happy that the two were going on. But it was nothing but a rumor as stated later, by both of them.

Joshua’s next girlfriend was Selma Blair and they reportedly started dating during the early part of 2010 and after they were photographed in LA, the shutterbugs were clearly hunting for another opportunity to see this hot couple together. Their relationship was mostly a secretive one and though, quite a few people spoke quite a few lines about them, nothing ever came out in public except for the fact that they were good friends. Sources even suggested that they were highly flirtatious while they were being photographed. They were supposed to be in a relation, before either of them was found to be in a different relation, putting gossip circles in a sudden fix.

The only girl, Josh ever came close to have thought of marriage with, was Michelle Trachtenberg whom he had reportedly started dating in 2012. Michelle had just started getting famous with her role in subsequent seasons of Gossip Girl. Josh and Michelle were widely seen as a cute couple and everyone wanted them to get hitched. It was known that they had separated amicably when Michelle was known to be dating pop-up artist and rapper Scott Mescudi, earlier this year.