While news of Kat Dennings and Andrew W.K.'s engagement [1] may have come as a shock to most [2], this isn't the first time Kat has surprised fans with her relationships. The 34-year-old actress typically keeps her love life private, famously denying any involvement [3] with Ryan Gosling [4] in 2009 and not confirming her relationship [5] with Josh Groban [6] until an appearance on The Ellen DeGeneres Show [7] in 2015.
If her recent engagement has you curious about who Kat has dated over the years, we've got you covered. It seems Kat prefers actors and singers as her dating history has a handful of names you will certainly recognise, including a Marvel man with a new show [8] on the way. Keep reading for a full rundown of Kat's dating history.
Ira David Wood IV
Although they never officially confirmed the status of their relationship, the pair were rumoured to have dated [9] in 2005. During this time, Ira accompanied Kat to the 11th annual Critics' Choice Awards and the premieres of both The 40-Year-Old Virgin and Pretty Persuasion. Best known for his role as Jay on One Tree Hill, Ira is also the older brother of actor Evan Rachel Wood.
Matthew Gray Gubler
Kat dated the Criminal Minds [10] star for a few months in 2007 [11]. It seems the breakup was amicable because in 2015, Matthew opened up to Glamour about his relationship with Kat, saying, "I'm still really good friends with her [12]. I love Kat. She's the best."
Ryan Gosling
Ryan and Kat were spotted [13] on a Disneyland date back in 2009, immediately sparking romance rumours. Kat never confirmed or denied the supposed relationship, but she did tell MTV News at the time, "I don't know [14]. I can't talk about my personal life."
Tom Hiddleston
The Thor costars dated briefly [15] in 2010, even holding hands while attending Comic-Con [16] that same year. However, their relationship had ended by Thor's 2011 premiere.
Nick Zano
Kat began dating her 2 Broke Girls costar [17] at the end of 2011. The pair met while working on the show, with Kat telling Glamour of the relationship in 2012, "Yes! I have nothing to hide! It's the truth! He's the best! [18]" Much like the characters of Max and Johnny on the show, the relationship wasn't meant to last and they called it quits in 2014.
Josh Groban
The couple started dating in October 2014 after Kat was introduced to Josh by her 2 Broke Girls costar [19] Beth Behrs. "He's just a genius [20]," the actress gushed to Ellen DeGeneres [21] in 2015. Josh expressed similar sentiments during his own appearance on The Ellen DeGeneres Show that same year, saying, "Humour is such a huge thing for me, so, you know, 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 [22].'" They dated until August 2016 when the pair mutually decided to break up [23].