A Look At Kat Dennings' Star-Studded Dating History

Kat Dennings has mastered the art of portraying sad girls in Hollywood, most of whom have complicated love lives. Since stepping into the scene as Jenny Brier in the multi-award-winning series "Sex and the City," Dennings has had a couple of notable sad girl roles. In the People's Choice Award-nominated series "2 Broke Girls," Dennings plays Max Black, a skilled cupcake baker whose impoverished roots influence her view of life. When it comes to romantic relationships, Black has several no-strings-attached encounters, and whenever things get serious with a potential partner, she's quick to fall into self-defeating patterns.

In real life, Dennings resonates with the relationship woes of most of her characters, as she shared in a chat with InStyle. "I am attracted to roles I feel like I can bring a real aspect to, you know, like I can actually draw from something," the actor told the publication. "I've had a storied love life and a somewhat interesting upbringing, so I feel like I relate to those characters." Dennings' love life has, for the most part, been kept under wraps. However, one thing is clear: the actor's dating circle isn't too far from the entertainment industry. Keep reading for more on her star-studded dating history.

Kat Dennings and "One Tree Hill" actor Ira David Wood IV first sparked dating rumors when they were pictured getting cozy during the August 2005 premiere of "The 40-Year-Old Virgin." The pair couldn't keep their hands off each other, as several photos showed them tightly hugging and holding hands.

In a red-carpet interview at the event, 19-year-old Dennings covertly confirmed that she and Wood IV were in a relationship. When a reporter asked if she had any relationship advice for someone who wasn't good at dating, Dennings replied, "I'm terrible at dating." Her response immediately prompted Wood IV to burst out laughing, but Dennings continued, "I just lucked out with him [Wood IV]." She proceeded to reenact how quirky she gets when she's really interested in someone. 

Unsurprisingly, that wasn't the last of Dennings and Wood IV's red-carpet appearances. The duo showed up together at the 11th Annual Critics' Choice Awards in January 2006, during which they appeared to be more than friends since Dennings was pictured blowing a kiss at the "The Believers" actor.

Kat Dennings and actor Matthew Gray Gubler first crossed paths in 2005. At the time, Gubler was just getting started on his role as Dr. Spencer "Spence" Reid, the super intelligent BAU special agent on "Criminal Minds." The role was close to Gubler's heart, and it allowed him to make "smart, awkward people feel good about themselves," as he shared in an interview with Backstage.

On a personal level, however, playing Dr. Spencer Reid took up much of Gubler's time. In turn, he found it hard to juggle work and his relationship with Dennings. Gubler revealed in a chat with Glamour, "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. But we were always close, and now that she's on a show, I feel like she [Kat Dennings] understands!" The exact timeline of Dennings and Gubler's relationship isn't clear, but he told the publication that they dated "for a long time."

Despite Gubler's overwhelming schedule, the pair found the time to attend events together. In April 2007, the exes were pictured looking stunning at the 39th Annual Magic Castle Awards in the company of Gubler's "Criminal Minds" co-star Paget Brewster.

Besides being lovers, Kat Dennings and "Criminal Minds" actor Matthew Gray Gubler had a great friendship. Gubler explained in his conversation with Glamour that he often gets smitten by "wonderful people and people that can't be replicated," and added, "They are completely unique individuals, and those people are really rare and you can't let them go. You gotta be friends with them forever because if I'm going to date someone, it's a real big thing for me." As such, he stayed on good terms with Dennings after their breakup.

In 2014, the duo collaborated on the Richard Bates Jr. horror film "Suburban Gothic," in which Dennings portrays Becca Thompson, a bartender who helps jobless business graduate Raymond Wadsworth (Matthew Gray Gubler) track down a vindictive ghost. Per his interview with Glamour, Gubler had fond memories of working with Dennings, and their on-screen chemistry was made better by the fact that they had been part of each other's lives off-screen. "To make a movie with people you're dialed in with in real life is the closest thing to being in a band with someone," the actor remarked. "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."

In August 2009, an internet sleuth tweeted that they had seen Kat Dennings and "Barbie" actor Ryan Gosling at Disneyland. The tweet sparked rumors that Dennings and Gosling were an item, and the "Big Mouth" actor herself further fueled those rumors after she wrote in a since-deleted tweet (via Perez Hilton), "Got kidnapped to Disneyland today ... my eyes were closed until a big flashing Mickey balloon was in front of my face. Best surprise ever."

MTV News later caught up with Dennings at the Toronto International Film Festival, and when a reporter brought up the topic of her supposed association with Gosling, Dennings refused to give any details. "I can't talk about my personal life," the actor said (via FandomWire). "Ask me about my cat, though, I'll talk about my cat." Dennings additionally divulged that she hadn't watched Gosling and Rachel McAdams' award-winning 2004 flick, "The Notebook."

In July 2010, Kat Dennings and her MCU co-star Tom Hiddleston joined other "Thor" stars in a panel discussion at Comic-Con. Besides a hearty conversation on the then-upcoming film, Dennings and Hiddleston caught the attention of fans when they were seen being a bit flirty with each other at the event.

A subsequent YouTube video of the "Thor" co-stars having an exchange with the paparazzi that night surfaced. In the clip, a curious videographer asked Dennings, "If you were granted one superpower what would you pick?" The "Daydream Nation" actor thought briefly, then replied, "Invisibility." When the videographer further inquired how she would put her superpower to use, Dennings, who was holding Hiddleston's hand while giggling, said, "I'd use it right now."

The pair were hit with more dating rumors when they showed up to the red carpet looking cozy at the October 2013 premiere of "Thor: The Dark World" in London; they were photographed holding hands, and they went as far as planting a kiss on each other's lips. At the time of writing, neither Dennings nor Hiddleston has verified any dating rumors.

Actor Nick Zano played the role of Johnny, a bartender-turned-graffiti artist who was romantically involved with Max Black (Kat Dennings) on Season 1 of "2 Broke Girls." Zano's character made another appearance on a December 2012 episode of the show. Earlier that year, it was reported that Dennings and Zano had developed an off-screen relationship that was still in its infancy. When Dennings was asked if they were seeing each other in a September 2012 interview with Glamour, she said, " Yes! I have nothing to hide! It's the truth! He's the best! I didn't know him before the show."

The duo made several public appearances as a couple; they showed up to a Los Angeles Lakers and Houston Rockets game, where they were pictured sitting courtside and were spotted acting mushy at another game between the Lakers and the San Antonio Spurs. Dennings and Zano still appeared to be going steady when they attended the April 2013 premiere of "Iron Man 3" together, but despite being pictured on vacation in Hawaii a year later, it was reported that the couple had already parted ways by the end of 2014.

When Kat Dennings and rapper Drake first met, she was 19 years old. At the time, Dennings was shooting a film in Drake's hometown, Toronto, and the rapper wasn't worldwide famous just yet. Drake eventually amassed an audience and openly gushed over Dennings years later in a May 2011 tweet, writing, "Kat Dennings I just woke up out of bed to let you know you were a dime on Conan tonight. XO."

His tweet prompted many of his fans to reach out to Dennings, and not in a kind way, as she later recalled in an interview with "Chelsea Lately." Dennings told the stand-up comedian of alleged seduction rumors (via E! News), "He [Drake] said something, and 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." Dennings and Drake eventually went for a sushi dinner, during which the rapper's security was in tow.

Despite the duo having a platonic relationship, Drake has never shied from admitting his crush on Dennings. In an October 2011 interview with Elle, he revealed his intention to invite Dennings to his 25th birthday party and said, "I'm in love with her. She's really funny. But I think she's dating someone."

Kat Dennings and "You Raised Me Up" singer Josh Groban were set up by Dennings' "2 Broke Girls" co-star Beth Behrs, with whom Groban had been friends for a long time. The pair was spotted at many events together, including a Vanity Fair Oscar Party held in February 2015 and the June 2015 Tony Awards, where they showed subtle PDA.

While dating, Dennings and Groban often spoke positively about each other in public. The actor gushed about Groban's musical prowess in a December 2015 conversation with "The Ellen DeGeneres Show," saying, "Obviously, you know how talented and amazing he [Groban] is, but what you may not know is that he is one of those people who can sit at a piano and play anything ... he's a genius!" Groban, on the other hand, happily talked about their matching humor in an interview with Entertainment Tonight. "We share a great sense of humor," the singer said. "Nobody makes me laugh more than she does." 

Away from the cameras, Groban and Dennings had a calm and private relationship, which was a far cry from the hustle and bustle of celebrity life. Groban told E! News, "When our schedules finally cross, you know, 'cause she's working so hard, too ... we just like to be the most boring people ever."

Although Kat Dennings and Josh Groban were still dating in early 2016, the pair hardly made any public appearances together. One of their rare sightings was at a February 2016 pre-Grammy party held as a tribute to former Ticketmaster CEO Irving Azoff, where the duo was all lovey-dovey on the red carpet. Dennings later expressed how much they had a blast in an Instagram post. "We had the BEST time at Clive Davis's pre-Grammy bash," the "How May We Hate You" actor captioned a selfie of herself and Groban. "Always an honor to be invited and the performances were incredible."

Five months later, an anonymous source revealed to E! News that Dennings and Groban had parted ways. "It was a mutual breakup," they said, and added, "They are still friends and care about each other, but it's not the right time for them now as a couple." Groban, who's been previously linked to singer Katy Perry, later moved on with actor Schuyler Helford, with whom he made a red-carpet debut at the 2018 Tony Awards.

Kat Dennings played the role of Jules Wiley on the Hulu series "Dollface" from 2019 to 2022. Wiley's story is that of a young woman who begins to lean on female friendships after a breakup. In her conversation with InStyle, Dennings admitted that Wiley's storyline hit close to home, and she was inspired to portray her because of her relatability. "What drew me to this project initially was that I have done this, I have lost myself in a relationship, more than once," the actor told the publication. "That has been my pattern, to fall for someone and then I am just gone from the world. 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."

Being on the set of "Dollface" allowed Dennings to foster sisterhood connections of her own with her co-stars, Brenda Song, Shay Mitchell, and Esther Povitsky. Per Denning's interview with BuzzFeed, the quartet had long working days during which they bonded over mundane activities like sleeping and napping, amongst other unusual things. "The things we do on the show are not normal," Dennings told the publication. "Like, we share these very special activities and it's sort of an irreplaceable bond that we all have."

Kat Dennings and "Music Is Worth Living For" singer Andrew Fetterly Wilkes-Krier, popularly known as Andrew W.K., first interacted casually via X in 2014 when the actor replied to W.K.'s picture, writing, "You are a tall drink of milk AWK" (via Vanity Fair). Seven years later, Dennings and W.K. became Instagram official when the actor posted two pictures of her beau on the social media platform with a heart emoji as a caption. In a May 2, 2021, post, Dennings shared a picture of the singer kissing her forehead while she pouted lips, prompting fans to speculate that the duo was dating.

Luckily, the couple's fans didn't have to wait much longer for an answer. In a May 6, 2021, press statement, W.K. announced the date of an upcoming tour, released the track list of his September 2021 album titled "God is Partying," and unveiled a single dubbed "I'm in Heaven." W.K. also confirmed his relationship with Dennings in a press release for the album which stated (via Stereogum), "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."

In May 2021, Kat Dennings made her engagement to Andrew W.K. public in a series of Instagram pictures in which she flashed her emerald and diamond-cut ring. The couple's proposal was a joint one-of-a-kind effort, as Dennings recounted on "The Drew Barrymore Show." "We had a special moment that makes me believe in magic," Dennings narrated. "We were doing kissing, and we had, like, a shared feeling ... I was like ... 'This is my person. This is it. I can't live without him. This is the man I'm supposed to be with.' And we looked at each other, and we both proposed at the same time."

Dennings and W.K. eventually tied the knot in a small wedding of only 15 attendants held in their Los Angeles backyard in November 2023. The couple had explored grandiose wedding options, as they shared in an interview with Vogue, but their simple engagement set precedence for an intimate setting that was unlike the glitz and glam of Hollywood. "We realized that a small home wedding was too cozy to resist," Dennings, who wore an Alexander McQueen dress on her big day, told the publication. "Plus, all our stuff was there so we wouldn't have to pack anything." The actor was a hands-on bride who incorporated DIY solutions to create the perfect decor for their special day.