Nathan Fillion made a name for himself playing the titular Richard Castle in the ABC mystery drama Castle of the early 2010s. He also starred as Captain Malcom Reynolds in Joss Whedon's space Western drama franchise, Firefly.
Since 2018, he has been starring as John Nolan in the police procedural drama series, The Rookie, also on ABC. Over the course of a career that spans nearly three decades, Fillion has managed to amass a net worth of about $20 million.
Despite this kind of phenomenal career and financial success, the actor has defied societal expectations, by remaining a bachelor - at his ripe, current age of 50. As things stand, he is believed to be single, although the history of his dating life has been anything but boring.
The Canadian-born star has been in at least seven known relationships since he rose to public attention. Impressively, though, he appears to have the ability to draw the line between business and pleasure, as he rarely ever dates his regular, on-screen colleagues.
The one time when Fillion was publicly known to have been involved with a co-star was in 2009, when he started going out with fellow actor Felicia Day. The two had worked together on the 2008 musical, limited series Dr. Horrible's Sing-Along Blog - another Joss Whedon project, which was made exclusively for internet distribution.
The comedy-drama musical is described as 'the story of Dr. Horrible, an aspiring super-villain, Captain Hammer, his superhero nemesis, and Penny, their mutual love interest.' Fillion portrayed Captain Hammer, as his rival character was played by Doogie Howser star Neil Patrick Harris.
Day stepped into the shoes of Penny, the kind and idealistic love interest of the two main characters. They were also joined on the cast by Simon Helberg - who would later become famous for The Big Bang Theory - as Dr. Horrible's sidekick, Moist.
Fillion and Day were often seen together out and about that year, although they never publicly spoke about their involvement with each other. It is also not known exactly when they went their separate ways, but by the following year, Fillion had already moved on to his next relationship.
Before all this happened, Fillion was actually engaged for a short time, to General Hospital and Beverly Hills, 90210 star Vanessa Marcil in 1996. The actress, who had been previously married to Corey Feldman in the '80s, had started going out with Fillion the year before. He proposed to her after about eight months of dating.
It wasn't long until the relationship altogether ended, however, as they split up after a little over six more months. Marcil is not Fillion's only ex-fiancée, as he has actually been engaged two more times after that.
In 2013, he popped the question to Anger Management star Mikaela Hoover, who said yes as they began to plan for a life together. This did not last very long, either, as he soon fell head over heels for Spanish science communicator, producer and actress Christina Ochoa.
Fillion and Hoover terminated their engagement in 2014. In the same year, he and Ochoa were pledged to be married to each other. Once again, though, the relationship ended just as fast as it had started, and the actor seemingly decided to break the habit of getting engaged only to end up separating.
Other women that Fillion has been involved with include Perrey Reeves and Krista Allen, who both represent his longest relationships ever. He went out with Entourage star Reeves between 2004 and 2009, while his romantic involvement with Allen lasted between 2010 and 2015.
Fillion's relationship with the latter was perhaps the one that gained most public interest. This most likely had to do with the fact that she is one of many women who have been linked to George Clooney in the past, before he met his current wife, Amal Clooney (formerly Alamuddin).
For about one year between 2010 and 2011, Fillion also had a fling with Shanghai Noon star Kate Luyben. Like him, Luyben is also Canadian. Soon after their relationship ended, she got involved with Australian comedian Jim Jefferies, with whom she now has a 9-year old son called Hank.
Interestingly, Fillion's intriguing relationship with women does not end in the romantic, as he also has a complicated history with his Castle co-star, Stana Katic. The two were reportedly at loggerheads during the making of the show, although he eventually tweeted his support of her after she was fired in 2016.
'I wish [Stana] well and have no doubt she will succeed in everything she pursues. She will be missed,' he wrote.
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