Kat Dennings's Relationship History Proves She's the Queen of "I Didn't Know They Dated"

Published on 5/14/2021 at 6:45 PM

While news of Kat Dennings and Andrew W.K.'s engagement may have come as a shock to most, 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 with Ryan Gosling in 2009 and not confirming her relationship with Josh Groban until an appearance on The Ellen DeGeneres Show 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 recognize, including a Marvel man with a new show 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 rumored to have dated 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 star for a few months in 2007. 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. I love Kat. She's the best."

Ryan Gosling

Ryan and Kat were spotted on a Disneyland date back in 2009, immediately sparking romance rumors. Kat never confirmed or denied the supposed relationship, but she did tell MTV News at the time, "I don't know. I can't talk about my personal life."

Tom Hiddleston

The Thor costars dated briefly in 2010, even holding hands while attending Comic-Con that same year. However, their relationship had ended by Thor's 2011 premiere.

Nick Zano

Kat began dating her 2 Broke Girls costar 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!" 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 Beth Behrs. "He's just a genius," the actress gushed to Ellen DeGeneres in 2015. Josh expressed similar sentiments during his own appearance on The Ellen DeGeneres Show that same year, saying, "Humor 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.'" They dated until August 2016 when the pair mutually decided to break up.

Andrew W.K.

They first sparked dating rumors at the end of April 2021 when Kat shared a photo of Andrew on Instagram, and shortly after, Andrew confirmed the relationship in a press release for his "I'm in Heaven" music video. "In other news, ANDREW W.K. has recently begun dating actor Kat Dennings," the statement read. "The two met earlier this year in Los Angeles. ANDREW W.K. and his ex-wife, Cherie Lily, began amicable divorce proceedings in late 2019."

Less than a week later, they surprised everyone when they announced their engagement via a series of photos on their respective Instagram accounts. "Don't mind if I do," Kat captioned the gallery. The actress also changed the link in her Instagram bio to his online shop.