Blake Lively is peeling back the curtain on her whirlwind romance with Leonardo DiCaprio, revealing untold details about the Hollywood heartthrob who once swept her off her feet. The Gossip Girl alum, now 37 and happily married to Ryan Reynolds, dropped the bombshell during a candid chat on The Drew Barrymore Show to promote her latest film, It Ends With Us. And fans are buzzing over what she had to say about the Oscar winner she dated back in 2011.
“I’ve never really talked about Leo,” Blake began, sipping a mug of tea as Drew leaned in eagerly. “But looking back, he was this wild card in my life—a total departure from who I was then. I mean, I was 23, fresh off Gossip Girl, and suddenly I’m on a yacht in Italy with Leonardo DiCaprio. Who lives like that?”
The pair’s romance, though short-lived, was the stuff of tabloid dreams. They met while Blake was filming Green Lantern and Leo was riding high off Inception. What followed was a five-month jet-setting fling—think Monaco Grand Prix dates, Leonardo’s infamous bike rides in NYC, and cozy dinners in Cannes. But it ended as quickly as it began, with little explanation—until now.
“Leo was intense,” Blake admitted, her signature laugh softening the confession. “He’s got this magnetic energy—everyone knows that—but it’s paired with this restless curiosity. One minute we’re debating climate change, the next he’s showing me how to spot constellations from his boat. I learned more in five months with him than I did in five years of school.”
So why spill the tea now? Blake said it’s all about perspective. “I’m in such a different place—married, four kids, settled,” she explained. “I can look back and appreciate what that time was: a crazy, beautiful detour. Leo was a chapter I needed to write Serena van der Woodsen out of my system.”
Fans on X wasted no time dissecting her words. “Blake calling Leo a ‘wild card’ is sending me,” one user posted, alongside a throwback pic of the duo. Another theorized, “She’s hinting he broke her heart—‘detour’ screams rebound vibes.” But Blake was quick to clarify there’s no bad blood. “People always want a villain,” she told Drew. “Leo wasn’t that. We just weren’t endgame—he was chasing his path, and I was finding mine.”
Rumors have long swirled that Leo’s notorious aversion to commitment (and his penchant for dating women under 25) doomed the relationship. Blake sidestepped that narrative with a sly grin. “Let’s just say our clocks were ticking at different speeds,” she quipped. “I wanted roots; he wanted wings. But I’ll always root for him—he’s one of a kind.”
The actress also debunked a fan-favorite myth: that Ryan Reynolds, whom she met shortly after the split, “stole” her from Leo. “Oh, please,” she laughed. “Ryan and I were friends first—Leo was out of the picture by the time we got together. Timing’s everything, right?”
Leonardo, now 50 and still making headlines for his love life, hasn’t responded to Blake’s comments. A source close to the Titanic star says he’s “not surprised” she’s reflecting fondly. “Leo’s always respected Blake,” the insider shared. “He thought she was smart, grounded—different from the Hollywood crowd.”
Meanwhile, Ryan Reynolds, 48, couldn’t resist chiming in. During a red carpet interview for Deadpool & Wolverine, he jokingly said, “Leo? Oh, I owe him a thank-you note. He left the door wide open for me.” Blake, standing beside him, playfully elbowed her husband, adding, “Yeah, but I upgraded.”