Are Drew Starkey and Cailee Spaeny Dating? Here’s Why Fans Think They Had a Falling Out With Odessa A’zion

Hi, welcome to the side of the internet that’s way too invested in whatever the hell Drew Starkey, Cailee Spaeny, and Odessa A’zion have going on. The trio goes way back—separately, of course—but were all cast in A24’s upcoming adaptation of Deep Cuts before Odessa pulled out last minute due to backlash.Aside from that, internet sleuths and fans alike have picked up on a potential vibe shift between all three actors. Drew was reportedly dating Odessa for literal years before he sparked new rumors with Cailee after production on Deep Cuts wrapped this spring. Oh, and somehow, Margaret Qualley and some Instagram unfollows are involved too. Confused? So are we. Here’s a full timeline of the rumored drama between Drew Starkey, Cailee Spaeny, and Odessa A’zion…because it’s kind of a lot.Jump to:November 2020October 2021November 2022December 2025January 2026February 2026May/June 2026August 2026September 2026November 2020Odessa gives Cailee a tattooIt’s unclear how far back these two go, but they must have been pretty close if Cailee trusted Odessa with a tattoo gun. According to Odessa’s sister, Gideon, the Marty Supreme star inked “1998,” the year Cailee was born, on the back of her neck in 2020.October 2021Drew and Odessa play love interests in Hulu’s Hellraiser rebootDeadline reports that Odessa and Drew are set to star as love interests Riley and Trevor in Hulu’s Hellraiser reboot.November 2022Odessa and Drew spark dating rumors for the first timeOdessa dropped a really sweet tribute for Drew’s birthday, which marks the first time people side-eyed their connection. I.e., are they friends, or something more?These two have made several public appearances together over the years, but have never explicitly defined their relationship status publicly. Whether these two were exclusively dating remains a mystery, but several sources claim they’ve seen a profile for Drew on Raya. A source separately told DeuxMoi’s Deux/U podcast that Odessa was “allegedly into him more than he was into her.”December 2025Drew and Cailee are cast in A24’s film adaptation of Deep CutsAccording to Deadline, Drew and Cailee are cast as the romantic leads in A24’s film adaptation of Holly Brickley’s Deep Cuts, which follows “two music-obsessed twentysomethings navigating the messy realities of ambition, belonging and adulthood” in the 2000s.January 2026Odessa pulls out of Deep Cuts shortly after casting backlashOdessa’s casting in Deep Cuts was later announced on January 26, only to receive backlash from fans. She was initially set to play Zoe Gutierrez, a character of Mexican and Jewish heritage, before backing out of the film altogether.“It is SO important for me to let you in on how it all went down: I went in for Percy, but was offered Zoe instead and instantly said yes!” Odessa explained, in part, on her January 28 Instagram Stories. “I’m so pissed y’all, I hadn’t read the book and should have paid more attention to all aspects of Zoe before accepting…and now that I know what I know??? Fuck that! I’M OUT.”Odessa A’zion//InstagramFebruary 2026Filming for Deep Cuts beginsAfter Odessa’s role was recast, Deep Cuts went into production, which likely means that Drew and Cailee bonded on set. Eagle-eyed fans even caught them following each other on Apple Music.May/June 2026Drew sparks dating rumors with his King Snake costar, Margaret QualleyDrew stays booked and busy. He started filming another movie, King Snake, alongside Margaret Qualley, whose split from Jack Antonoff was reported soon after. They sparked dating rumors when spotted at a minor league baseball game in Little Rock, Arkansas, on May 30.Drew and Margaret were also photographed at a swimming pool a few days later, though the rumors were never confirmed or denied.August 2026Cailee seemingly unfollows Odessa on social media and sparks new dating rumors with DrewCailee’s followers clock that she unfollowed Odessa on social media, which leads them to investigate further.Cailee Spaeny//InstagramAccording to their findings, it turns out Odessa still follows Cailee…Odessa A’zion//InstagramOn top of ^^^ that, a few DeuxMoi tips claim that Drew has been spotted with an unidentified woman on multiple occasions at the Atlanta airport and at a viewing of Death of a Salesman in New York.Internet sleuths quickly theorized that the mystery girl might be Cailee, according to similar sunglasses and clothes she’s previously worn.Again, this is unconfirmed! But still interesting.September 2026Drew and Cailee fuel romance rumors when they’re spotted hanging out togetherShortly after fans speculated a potential off-screen spark between Drew and Cailee, they were photographed hanging out together on September 2.According to screenshots, another fan on TikTok confirmed that Drew was also with Cailee on September 1 in London.That being said, it’s unclear if anything is going on here (if at all), but thank you for coming along on this v nosy journey!!