Kate Hudson and Owen Wilson Had the Most Uncomfortable Exchange Months Before They Started Dating

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time. 

Who: Oscar-nominated actress and businesswoman Kate Hudson, 40, and Oscar-nominated actor and writer Owen Wilson, 50.

MTV TRL With Kate Hudson, Beyonce, Owen Wilson, Shawn & Marlon Wayans
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How They Met: The pair met on the set of the 2006 comedy You, Me and Dupree while Hudson was still married to her first husband, Black Crowes singer Chris Robinson. A month after the film opened in July, Hudson and Robinson separated, with Robinson filing for divorce that November. She and Wilson were confirmed to be dating that fall.

Given the timeline and her onscreen chemistry with Wilson, it was long-rumored that there was overlap between the relationships, but Hudson countered the speculation simply, telling Harper’s Bazaar, “That’s not what happened.” Still, in retrospect it’s hard to watch Wilson ask Hudson about wearing a bikini in the film (6:50) on the press tour and not cringe just a little. Oh, and this bit (4:25) where he asks her whether she and her husband have ever had a "third wheel experience" is also not great ... Both Wilson and fellow co-star Matt Dillon also reportedly admitted to developing crushes on Hudson on set — but, like, it’s Kate Hudson, so who wouldn’t?

Why We Loved Them: Kate and Owen were as low-key as it gets. Though they were two of Hollywood’s most in-demand stars at the time, they kept their relationship as off-the-radar as possible. A three-year series of break-ups and make-ups allowed us to believe a reunion was possible well into the 2010s. Don’t tell anyone, but there’s a ~chance~ we’re still rooting for them …

When They Peaked: This photo:

Beyonce, Kate Hudson, Owen Wilson, Shawn Wayans and Marlon Wayans Visit MTV's
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The duo co-hosted an episode of Total Request Live (R.I.P.) in 2006 and something had them feeling confused/surprised/philosophical. Whatever it was, they were clearly on the same page.

The Breakup: Which time? By June 2007 round 1 of Kowen had come to an end. A few months later Wilson’s life took a nearly fatal turn when he attempted suicide. Sources close to the actor denied the correlation between his attempt on his life and his split from Hudson.

“Owen is such a lovely person, and I love him dearly,” Hudson told Vogue in late 2007. “And I wish him beautiful things — health and everything that he desires in life.”

"You, Me, and Dupree" World Premiere - Red Carpet
L. Cohen/Getty Images

Still hounded to discuss her role in her ex’s highly personal troubles years later, she told The Telegraph, “There are things that should be left alone and not discussed in public, and that was one of them. The media does not discriminate between people who want that attention and people who just want to get on with their jobs.”

By February of 2008 Hudson and Wilson had reunited, but once more it proved short-lived. They’d split by May, with a source telling People “It was a pretty bad breakup. Owen said it was a tough one. He definitely doesn’t want to dwell on it. He wants to put it behind him.”

Though just months prior Kate had revealed her “conscious decision to try to stay single as long as possible,” in February 2009 it was reported that they’d reunited. However, by May there was a new man in Kate’s life: Alex Rodriguez.

Despite the tumultuous nature of their relationship, there doesn’t appear to be any bad blood between the former co-stars. In 2012 it was reported that Hudson and Wilson had bonded over their children at the Vanity Fair Oscar party, giddily sharing photos of their respective tots.

When They Are Now:

Hudson welcomed her third child, Rani Rose, with longtime boyfriend Danny Fujikawa last October. She also shares 15-year-old son Ryder with Robinson and 7-year-old son Bingham with ex-fiancé Matt Bellamy.

The actress is set to star in Sia’s directorial feature debut, Music, expected to open later this year. She’s also slated to appear in Ana Lily Amirpour’s fantasy film Mona Lisa and the Blood Moon.

Wilson is also a father of three. The actor reportedly welcomed daughter Lyla with ex-girlfriend Varunie Vongsvirates last October. He’s also dad to son Robert, 8, with his air marshal ex Jade Duell and son Finn, 5, with his personal trainer ex Caroline Lindqvist.

It was recently announced that Wilson would star opposite Salma Hayek in sci-fi drama Bliss, but that’s hardly the only project on the horizon for the 50-year-old. Wilson will reprise his role in the Shanghai film series with Jack Chan in the third installment, Shanghai Dawn. He’s also rumored to be reuniting with Anaconda co-star Jennifer Lopez in upcoming STX rom-com Marry Me.

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