One of Josh's more notable relationships was to Kat Dennings. The couple had a very public relationship from late 2014 to 2016, when the two finally decided to call it quits. They both openly gushed about each other to Ellen Degeneres on her show, and the pair were known to have a shared nerdiness that brought them together. 

"She's, well, she's such a brilliant and funny person," Josh said to Ellen, ""Humor is such a huge thing for me, so the fact that we could talk about Monty Python and all sorts of weird other things, I was like, 'Ok, yeah, we're on the same page.'"

Their split in 2016 was amicable, according to E! News. The two decided on a "mutual breakup," and hold no hard feelings against each other. 

Before Kat, there was January Jones, who is said to be Josh's longest-lasting relationship. The two dated from 2003 to 2006, and were said to be "madly in love" during that time. Their breakup also was on good terms, and the two remained friends after the split. 

Other actresses Josh has been seen with include April Bowlby and Selma Blair. Schuyler is Josh's first public girlfriend since he and Kat broke up, and the pair seems to going strong.