Late-night TV doesn’t get more jaw-dropping than this! Nicole Kidman’s revelation on The Tonight Show left Jimmy Fallon in total shock—and 63 million viewers couldn’t look away. The Oscar-winning actress casually admitted she once had a huge crush on Fallon, but he completely missed the signals. As she unraveled the awkward truth, Fallon spiraled into chaos—stammering, facepalming, and even falling out of his chair in disbelief! The audience exploded with laughter as Fallon processed his life’s biggest “what if” moment. Was this the most hilariously awkward exchange in talk show history? See the cringeworthy moment unfold right here! 👇

Jimmy Fallon seems to have a clever quip for every situation, but the funnyman was completely lost for words after Nicole Kidman revealed that he had a shot at wooing her but epically failed on the first hurdle. In a hilarious 63 million view segment on The Tonight Show, Fallon mentioned their awkward first meeting as a brief funny aside, but was then completely blindsided when Kidman mentioned that she “liked him” at the time.

Fallon began by recalling that Kidman and their mutual friend Rick dropped into the TV host’s New York City apartment, but he wasn’t ready for an A-list actress to casually drop into his place. Kidman then dropped her bombshell that she actually wanted to meet Fallon back then because she was single and had a bit of a thing for him. The Music Man readers will note that Fallon then went through the five stages of grief right there on The Tonight Show when he realized he blew his one chance to date Nicole Kidman.

Things continued to go from worse to worst for poor Jimmy at this point, as Kidman took over the story to explain that Fallon greeted them in a baseball cap and a thrown-together outfit, and recalled that “you didn’t talk, you didn’t say anything.” She then did an impression of his awkward mumbling as Fallon continued to try and make sense of the revelation that was just dropped on him.

Kidman continued by saying, “And then you put on a video game or something, and I’m like ‘this is so bad.’” Fallon then cringed so hard he fell out of his chair, as Kidman continued with, “I swear that you didn’t talk at all. So after about an hour and a half I thought ‘he has no interest, this is so embarrassing.’” She then left, figuring that it was a lost cause. Fallon has a knack for setting up hilarious segments with A-listers, with another classic moment being Celine Dion’s wheel of musical impressions.

Jimmy Fallon fans among The Music Man readership may note that Kidman-gate left quite an impression on Fallon, as he has shared the awkward encounter several times, including on The Ellen Show and The Howard Stern Show. Now I’m sure we’ve all had an awkward first date in our time, but I guess we can be thankful that at least it wasn’t so awkward that it ended up on Jimmy Fallon, Ellen, and The Howard Stern Show for good measure!