When friends invited us to stay at the Four Seasons Hualalai on the Big Island, I was ecstatic. As an avid People magazine reader, I knew Hualalai was the place to observe celebs roaming in their natural habitat. Like tracking zebras and wildebeasts across the Serenghetti, this was my chance for an up-close encounter with a major movie star.
Unfortunately, it was a slow week at Hualalai. Most of the A-Listers had already migrated back to L.A., although I did spot Ed O’Neill pouncing on a warming tray of lobster mac and cheese at the 4th of July buffet.
But one day, when friends of our hosts met us for lunch, things began to look up. The woman, a down-to-earth mom named Shannon, casually mentioned Leonardo DiCaprio was hunkered down at Kukio, the even ritzier residential community next door.
BINGO! If Ed O’Neill was the kudu on the plain, then freakin’ Leonardo was the lion, rhino or jaguar of the big game celebrity hunt.
“Ohmigod,” I squealed like a tween at a Justin Bieber concert, “if he’s there tomorrow, will you puhleeze call me?”
Low and behold, the following day a text came through: Kim, Leo and his entourage are the only people on the beach if you want to come over.
I hightailed it over, rushing through the tasteful lobby and down the stairs toward the beach. Despite the hushed atmosphere, my heart thumped in my chest. Having been debriefed a day earlier, I kept my eyes peeled for a dude sporting a scruffy beard and much younger Victoria’s Secret model while furiously puffing on an electronic cigarette.
I arrived at the crescent of white sand beach out of breath. “Hi Shannon,” I huffed. “So nice of you to invite me.”
“Bummer!” she said. “You just missed Leo!”
It seemed Mr. DiCaprio and his smokin’ girlfriend had just strolled down the beach toward the Four Seasons!
Hoping to wash away my disappointment, I plunged into the turquoise sea and swam out to a raft moored to the ocean floor.
A few minutes later, Shannon’s husband, stand-up paddle boarded briskly in my direction.
“Hey Kim!” he called. “Shannon says to tell you Leo and his girlfriend just got back from their walk. They’re up by the pool.”
I butterflied back to shore faster than Ryan Lochte, and jumped into the jacuzzi, only to discover that once again, Mr. DiCaprio had eluded me. However, I did recognize a familiar face submerged in a fizzy cloud of jet bubbles a few feet away. I ran the man’s chestnut hair, facial scruff and lopsided smile through the thousands of celebrity faces I kept on mental file. Instantly his name came to me: Tobey McGuire. Spider-man & Leo’s best friend. Just wrapped “The Great Gatsby” together. Married to Jennifer Meyer, a jewelry designer. Daughter named Ruby. Blanking out on son’s name.
My 13-year-old, Saxon, was also chillin’ in the jacuzzi. “Sup’ mom,” he said, cool as a cucumber. “Just saw Leo.”
“Are you serious?”
“Yeah, he was wearing a fanny pack.”
“Eww. A fanny pack?”
“Uh huh. He just took off to go mansion hunting with his mom. I overheard him telling her to double time it.”
I sat for a while in the jacuzzi with Tobey, sneaking covert looks. Tobey was kinda pale and wore lobster-print swim trunks, the kind with built-in underpants that no legit surfer would ever be caught dead in. He seemed like any ordinary, slightly goofy dad.
After a few minutes, Sax jumped into the swimming pool and started a water fight with some scruffy thirty-something guy with disheveled hair, big doe eyes, hipster sideburns…Once again the data flowed, Rain Man style, into my brain…Lukas Haas, the kid from Witness. Also a member of Leo’s entourage. Last movie: Inception. He was horsing around in the pool with Ruby, showering her with attention. And another kid—Tobey’s kid. Otis.
Finally, I hauled my pruney body from the jacuzzi. At the towel station, I eavesdropped on some rich kids bragging about their Leo sightings. Everyone it seemed had a Leonardo story.
Everyone but me.
Dejectedly I headed home. Later that night I finally saw Leo—images of him on the black lava-fringed beach were splashed across the Internet courtesy of the paparazzi.
Thanks to the paps, at last I felt like I was right there up close and personal with Leonardo DiCaprio.

You’re hilarious! Great read!! Hope you catch him next time.
Hi lady! Oooooo, I loved this story and so feel your pain! If you and I were there together we could have been Charlie’s Angels in disguise and located him in a flash! I’m major stalker girl when I’m there and always feel like a giddy school girl if I ever see anyone famous! Why is that, I wonder?!?! Actually, Leslie Mann and Judd Apatow are my two best friends! Lol!
Lady! The funniest Hualalai story is still Stan metal detecting for Megan Fox’s lost engagement ring. Xoxo
Great post.. looking at the girlfriend I think I would have been running around shoulder to shoulder with you…
You’re sweet, Bulldog! I felt bad for his girlfriend because the internet was ablaze with mean comments about her saggy butt~ maybe that comes with the territory when you model for Victoria’s Secret!!
I loved your story! You are cooler than me. 😉
Thanks so much Ribonuff!
Kimmy! Kasey just had a sighting of him in Brooklyn. I got a text from her on Labor Day that said and I quote…”So, just saw Leonardo decaprio. Made my day!” She said he was scruffy too with a hat pulled down really low over his forehead. (I wonder if he went home and texted his mom that he saw Kasey that day?) Oh well. XXOOLA
That’s too funny, LynnAnne! He is all scruffy for Quentin Tarrantino’s new movie, Django Unchained. Honestly, Jimmyrexic blew poor Leo out of the water in the abs dept. haha!