Entertainment TV Kat Dennings and Andrew W.K.'s Relationship Timeline Kat Dennings and Andrew W.K. confirmed their whirlwind romance and surprise engagement in May 2021 By Katie Mannion Katie Mannion Twitter Katie Mannion is a contributing writer at PEOPLE. She has been working at PEOPLE since 2022. Her work has previously been published in Healthline, SheKnows and more. People Editorial Guidelines Published on July 8, 2022 11:02 AM Share Tweet Pin Email Photo: Axelle/Bauer-Griffin/FilmMagic Kat Dennings surprised her fans in May 2021 by announcing that she was engaged to singer Andrew W.K. The news came as a shock to many as the couple had only just revealed their relationship earlier that month. While the exact timeframe of their romance is unknown, Dennings previously revealed that her and W.K's engagement came as a surprise to the couple themselves. "Not planned. No knee down — I don't even remember what happened after that," she said during a February 2022 appearance on The Drew Barrymore Show. "We just were like 'Should we get married?' And 'Yes.' I just burst into tears." Since their Instagram debut, the ultra-private pair has remained fairly low-key. Still, the actress has shared a number of sweet, funny and flirty photos of the musician on social media. In many of the pictures, both Dennings and W.K. can be seen wearing rings, but the pair hasn't tied the knot just yet. From their online flirtation to their surprise engagement, here's everything to know about Kat Dennings and Andrew W.K.'s relationship. August 2014: Kat Dennings replies to Andrew W.K. on Twitter In 2014, Dennings and W.K. shared a brief exchange on Twitter before meeting in real life. Replying to a photo that the rocker shared of himself, Dennings tweeted, "You are a tall drink of milk AWK." At the time, W.K. was married to music producer Cherie Lily. Meanwhile, Dennings would go on to date singer Josh Groban later that fall. Dennings and Groban made their first public appearance as a couple in October 2014, but later went their separate ways in July 2016. A few years later, W.K. revealed that he and his then-wife had "began amicable divorce proceedings in late 2019," according to a press release he shared while announcing his new music and tour. Early 2021: Kat Dennings and Andrew W.K. meet and start dating Kat Dennings Instagram Dennings keeps her personal life fairly private, so it's unclear when exactly she started dating W.K. However, in May 2021, a press release for W.K.'s album, God is Partying, stated that the duo met "earlier this year in Los Angeles." April 29, 2021: Kat Dennings shares a photo of Andrew W.K. on Instagram Dennings and W.K. first sparked rumors of a romance in late April 2021 when Dennings shared two photos of the singer on Instagram. In the snaps, W.K. is pictured standing alone in a black T-shirt. The Dollface star simply captioned the post with a black heart. May 2, 2021: Kat Dennings and Andrew W.K. go Instagram official Kat Dennings Instagram Just a few days after hinting at a romance, Dennings and W.K. confirmed their relationship on Instagram. Dennings posted a photo of the pair together in which W.K. is seen kissing Dennings on her forehead. For his part, W.K. shared a similar snap of the couple kissing on his Instagram Story. May 9, 2021: Kat Dennings celebrates Andrew W.K.'s birthday Dennings celebrated the rocker's 42nd birthday by sharing another PDA-filled photo of the two on Twitter, writing, "Happy Birthday @AndrewWK ❤️" May 13, 2021: Kat Dennings and Andrew W.K. announce their engagement Kat Dennings Instagram Shortly after confirming their romance on Instagram, the couple shared another big announcement on social media: They were engaged! The actress shared three photos on Instagram showcasing her diamond ring with the caption "Don't mind if I do." The Celebrity Engagements of 2021 June 13, 2021: Andrew W.K. wears a ring in a birthday message to Kat Dennings Kat Dennings Instagram For Dennings' 35th birthday, W.K. shared a black-and-white photo of the couple on Instagram. Dennings reposted the picture on her own account with the caption, "the real 🎁." The snap showed W.K. wearing what appeared to be a wedding band on his ring finger, leading many to wonder if the couple had already tied the knot. July 14, 2021: Kat Dennings makes a cameo in Andrew W.K.'s music video On July 14, 2021, W.K. released his song, "Everybody Sins," along with a music video for the single. Dennings made a brief cameo in the video in which she kissed W.K. August 16, 2021: Kat Dennings shares a makeup tutorial with Andrew W.K. as her model A few months after announcing their engagement, Dennings shared a playful video of her fiancé on Instagram with the caption, "🤍Elegant Bridal Makeup🤍." In the video, Dennings applied makeup to a shirtless W.K. as the singer vaped and laughed. "You really look incredible, already," Dennings said, later adding, "You're so beautiful, do you know that?" During the makeup tutorial, Dennings continued to admire W.K. At one point, she shared how much she loved her fiancé's dimples before giving him a kiss. September 10, 2021: Kat Dennings praises Andrew W.K.'s latest album On Sept. 10, 2021, W.K. released his sixth studio album, God is Partying. That same day, Dennings shared a photo of W.K. performing on Instagram, writing, "⚫️NEW ALBUM OUT NOW⚫️ @andrewwk did it again for the first time with 'GOD IS PARTYING' do yourself a favor and let it into your ear holes/heart area!" Shortly after the album was released, W.K. deleted all of his social media accounts. February 11, 2022: Andrew W.K. guest-stars on Kat Dennings' show W.K. made a guest appearance on a season 2 episode of Dennings' Hulu series, Dollface. In the episode, the real-life couple shared an on-screen kiss. February 14, 2022: Kat Dennings shares why she and Andrew W.K. already wear their wedding rings Kat Dennings Instagram During an appearance on The Ellen DeGeneres Show in February 2022, Dennings cleared up the marriage rumors she and W.K. had sparked in June 2021. While speaking about how she and W.K. were already wearing their wedding bands, the actress said, "We're not married yet, but we went to buy our wedding bands and we were like, 'Why don't we just wear them? Who cares!' And that's the end of that story." February 16, 2022: Kat Dennings calls her past tweet to Andrew W.K. "strange and magical" In an interview with Bustle, Dennings spoke about her flirtatious 2014 tweet calling Andrew W.K. "a tall drink of milk." "I don't even remember doing that," she told the outlet, saying that even back then, she thought W.K. was a "talented, amazing genius." "I've just always admired him," the actress added. "And so, it is a very strange and magical update to that story." Dennings also credited W.K. with helping her manage stress, saying that the musician stops her from becoming overwhelmed. "Finding the right person, being really comfortable, and feeling at ease. It's a tall order, but it can be done," she said. February 21, 2022: Kat Dennings reveals how Andrew W.K. proposed While appearing on The Drew Barrymore Show in February 2022, Dennings shared more details about her engagement to W.K. "We had a special moment that makes me believe in magic," the Thor actress said before describing how the pair sharerd an intense feeling towards each other. "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," she recalled. Explaining how overwhelming and unexpected their joint proposal was, Dennings said, "I made it through the wilderness and found this incredible person, and yeah. No one believes me. But I assure you, that's what happened." May 9, 2022: Kat Dennings shares a sweet birthday message for Andrew W.K. Kat Dennings Instagram For her fiancé's 43rd birthday, Dennings celebrated the occasion with a funny Instagram message. The actress shared a photo of the couple taking a selfie together along with an image of the fictional Harry Potter character, Sirius Black, writing, "Happy birthday to the sweetest, most wonderful man in the world, who has NO relation to AI-generated Sirius Black. None. Zero." June 23, 2022: Kat Dennings and Andrew W.K. make their red carpet debut Momodu Mansaray/WireImage After being engaged for over a year, Dennings and W.K. finally made their red carpet debut in June 2022. The couple appeared together at the Los Angeles premiere of Thor: Love and Thunder. Though Dennings is reportedly not featured in the fourth installment of the Marvel Cinematic Universe (MCU)'s standalone Thor films, she is an MCU alum. She portrayed Darcy Lewis in 2011's Thor and again in 2013's Thor: The Dark World. In 2021, the actress reprised the role for the Disney+ series WandaVision. On Instagram, Dennings shared a photo of the couple's first stint on the red carpet with the caption, "♥️⚡️."