Jimmy Fallon Tells the Breakup Story That Ruined His Last Trip to Hawaii — and How He's Still Planning to Make Up for It (Video)

Jimmy Fallon is winning in 2020. He kicked off the year by teaming up with Michelob Ultra for his first-ever Super Bowl commercial. The one-minute ad couldn’t be more hilarious as it featured the late-night talk show host attempting to keep up with John Cena’s workout routine. He also had to play a round of beach volleyball with Kerri Walsh Jennings and run laps with Usain Bolt. As someone who’s better known for beer and pizza marathons in New York City’s East Village, this was a major accomplishment.

Another goal he wants to tackle this year is to travel more, specifically to the islands of Hawaii. “I had the worst vacation of my life in Hawaii,” he told Travel + Leisure. “This is a real story. I was with this girlfriend during Saturday Night Live and I had never been on vacation throughout the show. I kept working, working, working, so I go, let’s go on vacation. Let’s go to Hawaii.”

It sounded like a dream getaway, but of course, something came up. “She broke up with me right before the trip,” Fallon shared. Did you just get a flashback of Kristen Bell ending things with a naked Jason Segel? Unlike "Forgetting Sarah Marshall," Fallon’s ex-girlfriend didn’t follow him to the Pacific coast, but he did end up moving forward with his plans. “I was like, you know what, I’m going to go by myself,” he said. “I flew out of New York, got to the hotel, and at first, I loved Hawaii.”

Between the warm breeze, clear blue waters, and stunning sunsets, what’s not to love? Sadly, it all went downhill. “The worst thing happened as soon as I left my room,” the star revealed. He went on a helicopter ride to get to know the destination and it immediately backfired. “I wanted to see the volcanoes, so we took off, the pilot played James Brown, and I felt good,” he recalled. “There was an elderly couple behind me in matching tracksuits. As we were going over a volcano, the woman started vomiting. A couple minutes later, I saw a hand come by my face and I went, ‘What’s up?’ and it was her husband who wanted to know if we had another bag.”

As you can imagine, Fallon thought he was going to lose it. Eventually, the helicopter made an emergency landing in a parking lot and everyone was able to get off. “It was the most disastrous thing ever,” he emphasized. “That’s not even the worst part. When we landed, the pilot said he had to ask, since it was protocol, if I wanted a DVD of the experience? I thought he was out of his mind because all I wanted was to go back to New York.”

Nonetheless, Fallon is ready to put it all behind him and re-do his time overseas with his wife, who’s a huge Hawaii fan. “I really want them to redeem themselves and I think they owe me one,” he pointed out. If he were to go back again, the comedian is certainly more prepared and even has a list of essentials he’d bring with him. “I would take one of those Evian spray bottles and a neck pillow,” Fallon mentioned. “Actually, I take that back. I don’t want a neck pillow because I feel like that’s too much. I'm not one of those people who take their shoes off during a flight, that’s a bit too comfortable.”

Jimmy Fallon
Dominik Bindl/Getty Images

Fallon indicated that’s actually a major pet peeve of his. “I’m not in your apartment, so don’t take your shoes off, I was raised to respect everyone’s space,” he explained. Last, but not definitely not least, Fallon can’t venture out sans bug spray. “Mosquitos love me,” he stressed. “I’m total bait, they’re attracted to me. I don’t know what it is, but they love my blood and bug spray is important when I travel.”

Fingers crossed that Fallon makes it to Hawaii. In the meantime, get inspired by his positive attitude on a terrible travel situation. Think about a time when you had a bad experience somewhere and challenge yourself to do things better the second time around.

Was this page helpful?
Related Articles