On a recent episode of The Tonight Show, Nicole Kidman joined Jimmy Fallon for a hilarious and revealing conversation about a surprising encounter from their past—a meeting that could have been the beginning of something more, but instead turned into one of the most awkward moments in Hollywood history.

1. The Setup: A Chance Meeting That Could Have Been More

The story begins years ago when Nicole Kidman was in New York City, and their mutual friend Rick, who had connections with both of them, played matchmaker. Rick told Jimmy that Nicole was in town and interested in meeting him, maybe even for a role in Bewitched. But what caught Jimmy off guard was when Rick added, “By the way, Nicole’s single, and she’s looking to meet you.”

Jimmy, naturally, was thrown into a bit of a panic. What does one do when Nicole Kidman, one of the biggest stars in Hollywood, is coming to your apartment? Jimmy was quick to call Rick for advice, asking what he should prepare. Rick suggested something simple, like cheese and crackers. But in typical Jimmy fashion, the comedian was ill-prepared. “I don’t have dinner parties,” he admitted, “I have video games and sneakers.”

So, what did Jimmy do? He rushed to a deli and grabbed whatever he could, including brie, a cheese he didn’t even know how to pronounce. “Brie?” Jimmy said, still confused by the situation.

As he frantically prepared, little did he know, this would be a night that would haunt him for years to come.

2. The Awkward Encounter: Nicole’s Disappointment

When Nicole Kidman arrived at Jimmy’s apartment, she was expecting a warm and engaging conversation. Instead, she was met with silence. Jimmy, who had no idea how to handle the situation, simply greeted her in a baseball cap and sat down to play video games.

Nicole, who was clearly interested in getting to know Jimmy better, was baffled by his lack of interaction. “You didn’t talk at all,” she said, recalling the moment. “You were like, ‘Hey. Mm. Mm. Mm.’”

Jimmy, in typical self-deprecating style, confessed that he was very nervous and didn’t know how to approach her. “I didn’t know this was a date,” he laughed. But to Nicole, the silence and awkwardness were hard to ignore.

After about an hour and a half of what Nicole described as “nothing,” she decided it was time to leave. “I thought, ‘He has no interest. This is so embarrassing,’” she recalled.

3. The Fallout: Did Jimmy Really Not Realize?

As the conversation continued on The Tonight Show, Jimmy couldn’t help but laugh at how oblivious he was to the situation. “I had no clue at all,” he admitted, clearly embarrassed. He explained that he didn’t even know it was supposed to be a date. “Maybe I’m just not good at reading signals,” he joked.

Nicole, on the other hand, was left wondering why Jimmy hadn’t made a move. “I thought maybe he was gay,” she laughed, adding a touch of humor to the awkward situation.

But as the audience burst into laughter, it became clear that this was one of those moments in Hollywood that could have turned out very differently if only Jimmy had realized the opportunity that was right in front of him.

4. A Second Chance That Wasn’t Taken

The story didn’t end there. Nicole revealed another surprising twist: during a dinner party at David Fincher’s house, they had another chance encounter. “My agent had said, ‘Jimmy’s going to be there. Maybe you’ll get a second chance to meet him,’” she explained. But once again, Jimmy missed the opportunity.

According to Nicole, she and Jimmy were lingering in the kitchen after the rest of the guests had left, waiting for Jimmy to ask for her number. But once again, he didn’t. “You were standing by the buffet,” Nicole said, laughing. “I thought, ‘Okay, is he really not interested in me?’”

Jimmy, still unsure about what happened, responded, “I didn’t even remember this! I didn’t think I was supposed to do anything.”

5. The Missed Opportunity: A Hollywood ‘What If’

As the conversation continued, it became clear that this could have been one of the biggest “what if” stories in Hollywood. What if Jimmy Fallon had taken the opportunity to talk to Nicole and asked for her number? Could they have started a romance? Could they have even worked together on a project?

“Could I have been with Nicole Kidman?” Jimmy mused. “Did I blow it?”

The audience couldn’t contain their laughter, but Nicole was quick to reassure Jimmy. “You made a much better decision,” she said, acknowledging her happy marriage to country music star Keith Urban. “Keith is a rock star. He’s way cooler than you, Jimmy.”

6. The Aftermath: Nicole and Jimmy Reflect on Their Past

Despite the missed opportunities, Nicole and Jimmy laughed off the whole situation. They both acknowledged that their encounter was a sign that they were just not meant to be. “I’m happily married with kids, and so are you,” Nicole said. “We both moved on.”

But as the conversation wrapped up, it was clear that Jimmy’s awkwardness and Nicole’s patience had given fans a hilarious behind-the-scenes glimpse into their early years in Hollywood. It was a reminder that even the biggest stars have their awkward moments and missed connections.

7. The Final Laugh: Jimmy’s Redemption?

As the show came to a close, Jimmy continued to joke about the encounter, admitting that he would never live it down. But in true Fallon fashion, he turned the awkwardness into comedy, making light of the situation and even cracking jokes about how he might have acted differently had he realized the situation.

Nicole, ever gracious, added, “It’s all in the past. We’re both happily married, and that’s what matters now.” But you could tell that there was still a part of her that couldn’t quite shake the awkwardness of that first meeting.

In the end, the story of Jimmy Fallon and Nicole Kidman became a legendary tale of missed opportunities, awkward silences, and a Hollywood “what if” that fans would never forget.