Kat Dennings is known for her role as the melancholic characters in Hollywood, often marked by their intricate romantic lives. She gained recognition playing Jenny Brier on “Sex and the City,” and later as Max Black in the acclaimed series “2 Broke Girls.” Max is a cupcake maker with a tough background, which shapes her outlook on romance. Her character’s relationships frequently involve hookups, and she tends to sabotage her chances at genuine love.
In a conversation with InStyle, Dennings shared her understanding of her characters’ struggles in love. “I’m drawn to roles that resonate with my real experiences,” she said, referencing her own tumultuous love life and background. Though she keeps her personal relationships largely private, it’s evident that her dating life often intersects with the entertainment world. Read on to explore her notable romantic history.
Kat Dennings and Ira David Wood IV: A Lucky Romance
Kat’s romance with “One Tree Hill” star Ira David Wood IV ignited in August 2005, where they were spotted being affectionate at “The 40-Year-Old Virgin” premiere. Their chemistry was apparent as they were seen embracing and holding hands.
During a red-carpet interview, Dennings subtly confirmed their romance, humorously admitting, “I’m terrible at dating,” to which Wood IV laughed. She humorously expressed, “I just lucked out with him,” highlighting her quirky side when she’s interested in someone. They were later spotted at events like the 11th Annual Critics’ Choice Awards in January 2006, where their camaraderie clearly suggested a deeper bond.
Matthew Gray Gubler: A Relationship Complicated by Scheduling
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Dennings’ relationship with Matthew Gray Gubler began in 2005 as he launched his role on “Criminal Minds.” Gubler, deeply passionate about his character, dedicated vast amounts of time to the role, which strained their relationship. He mentioned to Backstage that balancing his career was challenging during the first five years of the series.
Despite scheduling conflicts, they participated in events together, and in April 2007, they looked fantastic at the 39th Annual Magic Castle Awards alongside Gubler’s co-star, Paget Brewster.
Remaining Friends Post-Breakup with Matthew Gray Gubler
Kat Dennings and Matthew Gray Gubler, known for his role in “Criminal Minds,” shared a close friendship in addition to their romantic relationship. Gubler shared in a Glamour interview that he finds it significant to connect with unique individuals, stating that such people are irreplaceable and should maintain lifelong friendships despite any romantic endings. This sentiment allowed them to remain on friendly terms after their separation.
The two teamed up for the 2014 horror flick “Suburban Gothic,” where Dennings played a bartender assisting Gubler’s character, a recent graduate seeking to confront a ghost. Gubler reminisced about their collaboration, citing the benefit of working with someone you’re familiar with—it enhances the creative process, almost akin to being part of a band. “It’s a joy to create something together that surpasses individual efforts,” he added.
Kat Dennings dodges Ryan Gosling dating gossip
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In August 2009, rumors about a romance between Kat Dennings and Ryan Gosling ignited when someone tweeted about spotting them together at Disneyland. Dennings stoked the fire with a now-deleted tweet recalling a surprise trip to Disneyland. During the Toronto International Film Festival, when questioned about the speculation involving Gosling, she dismissed it, stating, “I can’t talk about my personal life,” but was more than willing to discuss her cat.
Later, MTV News tried to get insights from her on this topic, but Dennings maintained her silence, mentioning that even though she hadn’t watched Gosling’s film “The Notebook,” she was focused more on her own interests.
Was there a romance between Kat Dennings and Tom Hiddleston?
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Kat Dennings and her “Thor” co-star Tom Hiddleston created a stir in July 2010 at Comic-Con. Their playful interactions during a panel discussion raised eyebrows among fans. A YouTube video showcased their humorous exchange with paparazzi that night, where Dennings, while holding Hiddleston’s hand, quipped about her desire for invisibility.
Dating speculations resumed after they appeared cozy together on the red carpet at the 2013 premiere of “Thor: The Dark World,” even sharing a kiss. However, neither party has ever officially confirmed any romantic connection.
Kat Dennings and Nick Zano’s relationship
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Nick Zano, who played a bartender and graffiti artist named Johnny on “2 Broke Girls,” was romantically linked to Kat Dennings. Their off-screen romance lasted for approximately two years before they quietly parted ways.
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Kat Dennings and Nick Zano’s Romance
In 2012, it was revealed that Kat Dennings and Nick Zano were involved in a budding relationship off-screen while working on their show. When interviewed by Glamour in September, Dennings confirmed their relationship, stating, “Yes! I have nothing to hide! It’s the truth! He’s the best! I didn’t know him before the show.”
The couple attended several events together, including games for the Los Angeles Lakers, displaying affection at various matches. Their relationship seemed stable at the premiere of “Iron Man 3” in April 2013, but despite a romantic getaway to Hawaii in 2014, reports indicated they had ended their relationship by the year’s close.
Kat Dennings Clears Up Drake Rumors
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Kat Dennings first crossed paths with Drake when she was only 19, filming in his hometown of Toronto. Years later, after rising to fame, Drake publicly complimented Dennings via a tweet, leading to a surge in followers, many of whom were less than kind to her. In a chat with “Chelsea Lately,” Dennings recounted receiving numerous hostile messages from Drake’s fans after his tweet. Eventually, the two met over sushi, where Dennings found Drake to be very kind.
Despite not dating, Drake expressed his affection for Dennings in an interview with Elle, mentioning intentions to invite her to his birthday and describing her as someone he loved for her sense of humor.
Kat Dennings and Josh Groban’s Sweet Two-Year Relationship
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Kat Dennings began dating singer Josh Groban after being set up by her “2 Broke Girls” co-star Beth Behrs. They were often seen together at glamorous events, including the Vanity Fair Oscar Party and the Tony Awards, sharing warm moments in public.
Both Dennings and Groban spoke fondly of one another, with her praising his musical talents on “The Ellen DeGeneres Show.” Groban reciprocated her affection, describing their shared sense of humor, and expressing how much he enjoyed her company. The pair preferred to keep their relationship low-key, opting for quieter moments away from the public eye.
Mutual End to Kat Dennings and Josh Groban’s Relationship
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Though Kat Dennings and Josh Groban were still together at the start of 2016, they appeared together sparingly in public. Their infrequent public sightings included a pre-Grammy party in February 2016.
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Kat Dennings’ Journey Through Love and Life
Kat Dennings and Josh Groban’s Relationship Flashback
At an event honoring former Ticketmaster CEO Irving Azoff, Kat Dennings and Josh Groban were seen enjoying each other’s company on the red carpet. Dennings later shared her excitement in an Instagram post saying, “We had the BEST time at Clive Davis’s pre-Grammy bash. Always an honor to be invited and the performances were incredible.”
However, just five months later, an anonymous informant revealed to E! News that the couple had amicably ended their relationship. “They are still friends and care about each other, but it’s not the right time for them now as a couple,” the source stated. Following their split, Groban began dating actress Schuyler Helford, making their public debut at the 2018 Tony Awards.
Inspiration Behind Jules Wiley in “Dollface”
Kat Dennings portrayed Jules Wiley in the Hulu series “Dollface” from 2019 to 2022, focusing on a woman’s journey of rekindling female friendships post-breakup. In an interview with InStyle, Dennings revealed that Wiley’s experiences resonated with her deeply. “What drew me to this project initially was that I have done this; I have lost myself in a relationship more than once,” she noted. It was a pattern she recognized in herself, mentioning how her friends would comment on her tendency to disappear during relationships.
While filming “Dollface,” Dennings formed strong bonds with her co-stars Brenda Song, Shay Mitchell, and Esther Povitsky. In her chat with BuzzFeed, she recounted how they bonded over unusual activities during long work hours. “The things we do on the show are not normal,” she shared, indicating the unique camaraderie they developed.
Beginning of Kat Dennings and Andrew W.K.’s Romance
Kat Dennings and musician Andrew W.K., whose full name is Andrew Fetterly Wilkes-Krier, first connected in a light-hearted manner via X in 2014. They truly began dating years later and made their relationship public via Dennings’ Instagram in May 2021, where she posted photos of them together. One picture showed Andrew leaning in to kiss her forehead, which fueled speculation about their relationship status.
The pair officially confirmed their relationship a few days later. In a press release, W.K. announced new music and mentions Dennings, stating they met in early 2021, just as he was navigating a divorce from his ex-wife, Cherie Lily.
The Intimate Wedding of Kat Dennings and Andrew W.K.
Kat made headlines in May 2021 when she revealed her engagement to Andrew W.K. through Instagram photos displaying her stunning emerald and diamond ring. The proposal itself was a magical moment for both, as Dennings recounted on “The Drew Barrymore Show,” where they both proposed to each other simultaneously.
In November 2023, the couple celebrated a cozy, private wedding in their Los Angeles backyard, attended by just 15 guests. Although they considered larger venues, Dennings expressed a preference for an intimate setting, stating, “We realized that a small home wedding was too cozy to resist.” She also emphasized her hands-on approach, including DIY elements to personalize their special day and wore a beautiful Alexander McQueen dress.
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