Who: Oscar-winning actor and producer Leonardo DiCaprio, 46, and People's Choice Award-winning actress Blake Lively, 33.
How They Met: DiCaprio and Lively's paths first crossed (publicly, at least) in November 2010, when both parties were present at an 8-person dinner in N.Y.C. Lively was being considered for the role of Daisy Buchanan in Baz Luhrmann's The Great Gatsby (opposite DiCaprio's Jay Gatsby), so the outing was quickly classified as business.
A week later it was announced that Carey Mulligan had won the coveted role, and any fanfare around DiCaprio and Lively's dinner died down.
The following May, everything changed.
With the beginning of Cannes Film Festival, the most glamorous of celebrity fêtes, the most glamorous of celebrities appeared on the most glamorous of French Riviera-docked yachts. Among them: DiCaprio in his nightclub finest (aviator shades, perfectly faded jeans, and a blue dress shirt) and Lively in a summery white shirtdress and blush-hued oxford shoes. But it wasn't simply an appearance — they were hugging.
And with that, the impossibly bourgeois summer of "DiLively" commenced.
Why We Loved Them: For but a moment, it seemed perpetual bachelor DiCaprio may be ready to settle down. Unnamed Us Weekly "insiders" had "never seen him like this with a girl"! They held hands in Monte Carlo; they "seemed happy in each other's company" in Portofino; they skipped lines (!) together at Disneyland … And how could you forget the bikes? We love a couple who can look just as cool riding their bikes through the N.Y.C. streets as partying aboard a yacht.
Though the coupling may have seemed sudden to the untrained eye, DiCaprio had actually been on Lively's mind for a while. In 2007, the Gossip Girl star told CosmoGIRL! (RIP) that she "had a huge crush" on DiCaprio when she was a child. The Titanic actor and Justin Timberlake were named "the two I can really think of just being completely in love with."
When They Peaked: Years following DiLively's somewhat inevitable end, Gossip Girl executive producer Joshua Safran (who happens to be the GG reboot's showrunner), gave Vanity Fair a strange and surprising anecdote about the former couple.
Safran noted that during the period in which Lively was dating DiCaprio she "had this thing where she had a doll that she took photos of that she sent to Leo." Can the reboot be about that instead?
The Breakup: The breakup was reported about a month after Lively visited DiCaprio in Australia (where he was filming Gatsby) late that summer. Try as he might, Cuddles the diamond python couldn't keep DiLively afloat.
In October 2011, a People source noted that the split was "amicable" and that the actors remained friends. DiCaprio's "work commitments" reportedly played a role in the breakup.
Where They Are Now:
DiCaprio has been dating model and actress Camila Morrone since late 2017. The actor has several projects in the works, including Netflix's Don't Look Up.
Soon after splitting from DiCaprio, Lively began dating her Green Lantern co-star Ryan Reynolds (whom she wed in 2012 … on a plantation). The couple shares three daughters: James, 6, Inez, 4, and 21-month-old Betty.
Next up for Lively is Liane Moriarty's adaptation The Husband's Secret.
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