Margot Robbie’s Shot at Secrets: A Wild Ride Through Truth or Tequila with Jimmy Fallon

Byline: Late-night confessions, celebrity near-romances, and one unforgettable Valentine’s Day breakup — how Margot Robbie and Jimmy Fallon turned a drinking game into comedic gold.

In one of the most charming and chaotic segments to hit The Tonight Show Starring Jimmy Fallon, Margot Robbie joined Fallon for a revealing round of “Pour It Out,” a cheeky shot-glass game laced with personal questions, unfiltered answers, and high-octane humor. The premise is simple: each drink comes with a personal question written on the bottom of a coaster. Guests must silently read the question, decide whether to answer it aloud or keep it secret, and then choose to either share the question—or take the shot instead. But there’s a twist: one question must be revealed, no matter what.

What followed was a delightful spiral of heartfelt confession, mysterious references, celebrity name-drops, and one wildly awkward smooch story involving none other than basketball legend Michael Jordan.

The Valentine’s Day Breakup

Robbie’s first question hit harder than the shot in front of her—dubbed “Mary Queen of Shots.” She read the question to herself, visibly struggled, and then delivered a sheepish yet sincere answer: “Also, I’m sorry to do this on Valentine’s Day.”

Cue the collective gasp. Jimmy immediately pounced: “Did you break up with someone on Valentine’s Day?”

“Yes,” Robbie admitted. “It was awful.”

As the audience cringed and laughed in equal measure, Robbie explained that she hadn’t planned to deliver heartbreak on the holiday, but the conversation “arose,” and she couldn’t avoid it. Though she didn’t share the identity of her unfortunate ex, she confirmed it was a moment of deep regret. “I hope to God he’s not watching this,” she added, burying her face in her hands.

Brutal honesty, a touch of self-deprecation, and Margot’s effortless charm — it was the perfect cocktail to kick off the night.

“Howard Stern’s House”

Fallon followed up with a shot of his own. After reading his coaster’s mystery question, he simply muttered: “Howard Stern’s house,” before downing the spicy shot and refusing to elaborate.

The secrecy only made the moment funnier. “You’re never going to know,” he teased, clearly enjoying the torment of the unknown. The audience roared with curiosity, but Fallon stood firm — whatever happened at Howard Stern’s house will remain between him, the coaster, and the fiery tequila.

Will Smith and the “Adios, Mofos” Shot

Next came one of the most cryptic (and tantalizing) answers of the night. Robbie’s next shot — hilariously named “Adios, Mofos” — prompted another silence, a look of panic, and a straight-faced confession: “The answer is Will Smith.”

Fallon’s jaw dropped. “Is this about Suicide Squad?” he prodded, referencing their blockbuster DC collaboration.

Robbie remained coy, only admitting she’d done two movies with Smith and that there were “layers of complicity.” Was the question about on-set drama? A secret romance? A wild premiere night? She refused to say, opting instead to take the blue-hued shot and leave the audience hanging.

Let the fan theories commence.

Fallon’s Awkward Kiss with Michael Jordan

Then came Fallon’s chance to finally reveal one of his coaster questions — and it did not disappoint.

He boldly answered: “Michael Jordan.”

The question? “Who was your worst kiss?”

After the gasps settled, Fallon clarified that it was not Michael B. Jordan (which elicited more laughter), but the basketball icon himself.

He recounted a charity golf tournament hosted by Derek Jeter, which ended with a night at a dance club. Fallon went in for a friendly kiss on the cheek — a gesture Jordan misunderstood. The result? An accidental lip-to-lip encounter between the late-night host and the NBA legend.

Fallon reenacted the moment, sharing how Jordan calmly assured him, “Don’t worry about this,” with his strong arms and stoic demeanor. The audience lost it.

“He just held me and said, ‘You’re safe,’” Fallon joked. “It was very serious the way he said it. But it was very sweet too.”

The Almost-Romance with Kate Hudson

For the final round, Robbie and Fallon were tasked with answering the same question — or else drink beer from straws.

Fallon cracked first.

His answer? Kate Hudson.

The question? “Do you have a co-star you thought you could have dated but didn’t?”

He recalled their time filming Almost Famous, where he played a small supporting role. After the movie, the two became friends, and Fallon even took her to see a comedy show — “Kids in the Hall” — before going ice skating in Central Park.

Romantic? Almost.

But while Fallon thought there might be sparks, Hudson had other plans. During their skating session, she asked him to bring her some Black Crowes CDs. When they met up, she casually mentioned she had a date that night — with Chris Robinson, the band’s lead singer. They later married and had a child.

Fallon closed the story with mock devastation: “I never got my CDs back.”

Robbie’s Escape — and Masterful Evasion

And what of Margot Robbie’s answer to the final question?

She dodged it with style.

“I don’t have one,” she claimed, citing a personal rule that prevents her from fantasizing about co-stars. Fallon wasn’t buying it — and neither was the audience. But she held her ground, proving once again that she knows exactly how to walk the tightrope of Hollywood transparency without ever losing her balance.

A Toast to Truth and Timing

This “Pour It Out” segment was more than just celebrity gossip and booze-fueled antics — it was a masterclass in chemistry, improvisation, and late-night storytelling. Robbie’s comedic timing, Fallon’s vulnerable charm, and a lineup of unexpected confessions made it one of the most memorable moments in recent Tonight Show history.

Whether it was a Valentine’s Day breakup, a lips-on accident with Michael Jordan, or a never-meant-to-be romance with Kate Hudson, the segment captured the kind of spontaneous magic only live TV can offer — a little awkward, a lot hilarious, and surprisingly human.

In the end, America didn’t get all the questions. But the answers? Totally worth the hangover.