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Who: Oscar-nominated actor Jake Gyllenhaal, 38, and Oscar and Emmy-winning actress, producer, and businesswoman Reese Witherspoon, 42.
How They Met: Both actors starred in the 2007 drama Rendition, but didn’t share much time on set throughout the eight-week shoot in Morocco. During a reshoot in L.A. Jake reportedly reintroduced himself and things “slowly progressed,” with Reese developing “this little crush over time.”
That being said, the stars weren’t unfamiliar with each other before the shoot — in fact, Jake was reportedly Reese’s ex-husband Ryan Phillippe’s “old workout buddy” …
Why We Loved Them: I mean, they’re cute as hell. They’re like two wide-eyed woodland creatures who happen to also be talented actors with a shared passion for Lakers games.
When They Peaked: This may very well be a tabloid-spun tale, but there were reports in late 2007 that Reese and Jake were spotted entering the same airplane lavatory a few minutes apart and spent “11 minutes” (no more, no less) inside before returning to their seats. Take what you will from that highly off-brand story.
The Breakup: When Jake and Reese’s “little flirtation” began, she was still in the process of divorcing the father of her two children, Phillippe. So just months after they began dating in spring 2007, Witherspoon called things off. A source told People it was “totally and completely over” in June, noting, “She just got out of a divorce and was so concerned with her family, she just didn’t have the time for him and he really demanded that.”
But, of course, things weren’t “completely over” between them, and the pair was spotted cuddling up in Rome that October.
Two years later, in November 2009, Gyllenspoon ended for good.
There’s speculation that the split arose out of Witherspoon’s reluctance to remarry — she’d told Parade in 2008 that despite her strong commitment to family, she didn’t know how she felt about marriage. “Obviously, I’m not far enough out of being married to think about doing it again,” she said. “You sort of reconstitute your family. You find a family with people who come into your life for a reason.” Meanwhile, reports surfaced that “Jake would marry her tomorrow.”
My personal theory is that Reese just couldn’t handle the way he’d watch her eat — he has a pattern of wearing strange expressions while staring his girlfriends down mid-bite, you know.
But reason aside, things truly seem to be amicable. More than six years post-split in 2016, Gyllenhaal publicly called his ex “one of the smartest, strongest people I’ve ever met.”
Where They Are Now: In the years since their split, Reese launched a production company, started a fashion line, and won an Emmy.
Witherspoon wed talent agent Jim Toth in 2011 and welcomed son Tennessee in 2012.
Gyllenhaal remains Hollywood’s most eligible bachelor, though he’s rumored to be dating 23-year-old model Jeanne Cadieu.
The actor has several projects in development and appears to be turning his focus toward producing.
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