Inside Kat Dennings' Relationship History

Born Katherine Victoria Litwack, Kat Dennings made her screen debut at the tender age of 13, memorably playing a pushy bat mitzvah girl in an episode of "Sex and the City." That led her to be cast as the teenage daughter of Bob Saget's character in the sitcom "Raising Dad," sparking a successful acting career that just keeps expanding. So far, Dennings' journey through Hollywood has included headlining a beloved rom-com ("Nick and Norah's Infinite Playlist"), co-starring in a wildly popular network sitcom ("2 Broke Girls"), and becoming part of the Marvel Cinematic Universe (her character, Darcy Lewis, has appeared in several "Thor" movies, and the Disney+ series "WandaVision"). And those are just the highlights.

While her career continues to heat up, Dennings has chosen to keep her personal life mostly to herself. That hasn't always been easy, considering that she's dated several famous guys over the years — although Dennings was uncharacteristically candid about her love life in a 2019 interview with InStyle. "That has been my pattern, to fall for someone and then I am just gone from the world," she said. "One of my best guy friends actually says that I fall off the world. Which is true! It's something that I didn't even realize I was doing. Men and women do it. It's just a natural thing to do when you fall in love."

To find out more about those various romances, read on to venture inside Kat Dennings' relationship history.

She tried to keep her relationship with Ira David Wood IV out of the spotlight

Rumors that Kat Dennings was dating actor Ira David Wood IV first began swirling when the two were photographed together at the 2005 premiere of "The 40 Year Old Virgin," in which Dennings played the mopey teenage daughter of Catherine Keener's character. While neither Wood nor Dennings has ever publicly commented on their relationship, it's likely the two met on the set of the 2005 film "Down in the Valley," in which both he and Dennings had roles.

Wood — older brother of "Westworld" star Evan Rachel Wood — can be seen gazing adoringly at Dennings while she's in the midst of a red-carpet interview with Showbiz Junkies. "It was pretty much a crackup-fest," Dennings says of trying to keep a straight face while working with "40 Year Old Virgin" star Steve Carell. "If you don't see, in the Planned Parenthood scene, if you don't see my hand, it's because I'm pinching my thigh. That's a trick I learned — because I didn't think I'd be able to get through that scene at all." Wood also accompanied Dennings to the Critics' Choice Awards, and the premiere of the film "Pretty Persuasion," in which he appeared.

Wood, who played Jay on two episodes of teen drama "One Tree Hill," is currently the artistic director of Theatre in the Park — founded by his father, Ira David Wood III — in Raleigh, North Carolina. 

She briefly dated Criminal Minds star Matthew Gray Gubler (or maybe it was 'for a long time')

At some point in 2007, Kat Dennings began dating another actor, Matthew Gray Gubler, who played quirky profiler Dr. Spencer Reid on "Criminal Minds." Photographed together while attending the Golden Globes in January 2007, they reportedly only dated for a few months before breaking up.

In a 2015 interview with Glamour, Gubler confirmed that he and Dennings had been an item and remained on good terms. When asked if they'd dated, he replied, "For a long time. I'm still really good friends with her. I love Kat. She's the best." 

He shared more, revealing they first met right at the start of "Criminal Minds." "Kat is marvelous. She's one of the funniest people I know and such a talented actress, a brilliant mind, a warm-hearted person, and I love her and her family," Gubler said, hinting that they broke up because of the demands of his show. "Being on a show like this is not conducive to having a real life because for those first five years of 'Criminal Minds,' we were easily doing 15-hour days." Years after breaking up, the exes appeared together in the 2014 movie "Suburban Gothic," and Gubler described acting opposite Dennings as one of his favorite professional experiences. "It's so nice to have a creative force that you can create something better together than alone, and that's what it was like working with her," he said.

Kat Dennings' alleged Disneyland date with Ryan Gosling sparked romance rumors

Rumors that Kat Dennings had a new man in her life emerged when she and Canadian actor Ryan Gosling were spotted together at Disneyland in August 2009. According to Lainey Gossip, the evidence the two were dating wasn't exactly rock solid, consisting of a pair of tweets: one from somebody claiming to have seen them at the Magic Kingdom, and another from Dennings joking that she'd been kidnapped and taken to Disneyland (those tweets have long since been deleted). Meanwhile, Lainey Gossip pointed to further since-deleted tweets in which Dennings and the future "Barbie" star each posted similar photos of a car's tire — the same tire, but photographed from different angles. 

Neither Gosling nor Dennings has ever addressed the rumor — although that hasn't been from lack of media interest. In fact, a few weeks later, an interviewer for MTV News made a valiant attempt to get Dennings to either confirm or deny she and Gosling went on a date. 

Asked about being spotted with a "friend" at Disneyland, while on the red carpet at the 2009 edition of the Toronto International Film Festival, Dennings responded, "A friend? I don't have any friends," adding, "I don't know. I can't talk about my personal life." As the interview progressed, Dennings reiterated her stance about maintaining her privacy. "I do not talk about my personal life," she said. "Ask me about my cat, though, I'll talk about my cat."

Reports of an MCU fling with Tom Hiddleston remain unconfirmed

Kat Dennings joined the Marvel Cinematic Universe in 2011's "Thor." When she and co-star Tom Hiddleston — who played trickster god Loki — appeared together at San Diego Comic-Con in 2010, their affectionate behavior toward each other raised eyebrows. More fuel was poured on the fire when a video showed up on YouTube, in which Dennings is holding Hiddleston's arm while they stroll together. 

Those rumors fizzled out when Dennings and Hiddleston weren't seen together after that. However, more romance gossip was reignited when the two reunited for the 2013 sequel, "Thor: The Dark World." The two posed together at the film's premiere — with other members of the cast, and then just the two of them, as a couple would. Those rumors grew even stronger when the two shared a kiss in full view of photographers, as cameras clicked away. 

Giving even more credence to the alleged romance was the fact that Hiddleston was newly single; in early 2012, he confirmed that he and girlfriend Susannah Fielding had broken up. "The fact is we've split up. The relationship ran its course," Hiddleston told The Daily Mail. As he explained, he was focused on his acting career, which had heated up considerably thanks to his role as Loki. "It's just I am very driven right now and there isn't really any time to have a proper girlfriend," he added. Neither Dennings nor Hiddleston have confirmed nor denied that they dated.

Her relationship with 2 Broke Girls co-star Nick Zano lasted two years

In 2011, Kat Dennings landed what would prove to be the biggest role of her life: Max Black in the CBS sitcom "2 Broke Girls." It was there that she met fellow actor "2 Broke Girls" actor Nick Zano, who played the recurring role of Johnny in nine episodes during the series' first and second seasons. 

Dennings and Zano quickly hit it off and reportedly began seeing each other in the latter part of 2011. As a source told Us Weekly, the relationship was somewhat casual — at least initially. "Kat and Nick are getting to know each other right now," the source said of the pair, whose characters were romantically involved in "2 Broke Girls." "They are not exclusive but have gone on dates." However, things eventually became serious — or at least serious enough for Dennings to reference her "boyfriend" in a tweet (Dennings' account on the social media platform X, formerly Twitter, has been deleted).

By the following year, Dennings and Zano had made their romance official. In an interview with Glamour that was published in September 2012, Dennings was asked point-blank about whether they were dating. "Yes! I have nothing to hide! It's the truth! He's the best! I didn't know him before the show," she gushed. The two continued to be a couple for some time after that, but eventually, things ran their course. Dennings and Zano quietly split up at some point in 2014.

The truth about her rumored romance with rapper Drake

Kat Dennings met Drake when she was 19, while shooting indie film "Charlie Bartlett" in Toronto. At the time, the future rap superstar was an actor named Aubrey Graham, appearing in "Degrassi: The Next Generation." 

Dennings apparently made quite the impression on Drake, who told Elle in 2012 that he was planning on inviting her to his birthday party. "I'm in love with her," he said. "She's really funny. But I think she's dating someone." In 2013, he tagged Dennings in a tweet, something she didn't notice until her social media began blowing up. "What happened was, and I'm glad we're talking about this, Drake was super nice and said something on Twitter about me," Dennings explained during an appearance on "Chelsea Lately," as reported by Complex. "I didn't realize that happened. So when I got home, I had, like, 50,000 new followers out of nowhere ... they were like, 'F*** you, Kat Dennings,' and, 'You can't take Drake from me. He's mine.' And then I realized what had happened, and then we started talking and he's super, super nice. He's a lovely person."

To make up for all the abuse she'd received from his jealous fans, Drake took Dennings out to dinner. "We had sushi," she said, describing their meal together as "a hangout." She added, "He was a gentleman, he was cool ... but we were being followed by a black SUV with his security dude."

Kat Dennings and Josh Groban split after two years of dating

In the wake of rumors they were dating, Kat Dennings and singer Josh Groban made their first official appearance together as a couple at the Carousel of Hope Ball in October 2014. Interviewed at the event by "Extra," Groban revealed that they'd met through her "2 Broke Girls" co-star Beth Behrs, with whom he'd become friendly after they met on a talk show. "She played matchmaker," Groban said of Behrs. 

Groban opened up about their romance during an appearance on "The Ellen DeGeneres Show," explaining how their shared status as nerds cemented their bond. "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, 'Okay, yeah, we're on the same page,'" Groban said. 

Behrs, whose matchmaking skills brought the two together, gushed about what a great couple her sitcom co-star and the "You Raise Me Up" singer made. "They're in this crazy business, they're both very calm and mellow and wonderful," she told People. "And he treats her like a princess, and it's amazing." Sadly, it was not to last. In 2016, the two decided to call it quits after nearly two years of dating. "It was a mutual breakup," a source revealed to E! News. "They are still friends and care about each other, but it's not the right time for them now as a couple."

She got engaged to musician Andrew W.K.

Dating rumors arose in April 2021 when Kat Dennings posted a photo of musician Andrew W.K. on Instagram, accompanied by a single heart emoji. Two days later, she shared another photo of him, this time kissing her tenderly on the forehead. A few days later, he confirmed they were indeed a couple in a press release for his new single, "I'm in Heaven." In addition to info on upcoming tour dates, reported Stereogum, the release added, "In other news, Andrew W.K. has recently begun dating actor Kat Dennings. 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."  

Days later, the couple had another announcement to make. This time, Dennings handled the news-disseminating duties via Instagram, posting photos of herself showing off her diamond engagement ring. "Don't mind if I do," she wrote in the caption. Dennings' fiancé continued to pop up in her Instagram feed, including one steamy 2022 Valentine's Day shot of the two kissing. That same day, Dennings made an appearance on "The Ellen DeGeneres Show," where she displayed her ring for viewers. "I accidentally got on purpose engaged!" she joked.

In May 2022, the two were still going strong when Dennings once again took to Instagram, sharing a sweet birthday tribute. A few months later, the two made their red carpet debut when he accompanied her to the premiere of "Thor: Love and Thunder."