The Day I Went To Oprah’s House

The other day, when we were in Hawaii, I was super-tired and a little bit cranky. I’d arranged for our sofa bed to be made up while we were at dinner and when we got back, it wasn’t. At that stage we’d been up for a gazillion hours, having flown in that morning, so I took my weary self and Lacey down to the front desk {the phones didn’t work} and asked if they could come up and help me put it together.

They said yes.

So then we hotfooted it back to our room, and as we exited the lift I saw a man and a woman leave the room next door to us. The lady smiled and said hello. The man drank from his water bottle. I took one look and realised it was KEVIN HART. I mean, I’ve never watched any of his movies, but I’ve seen in him in loads of interviews and the guy is funny.

So I calmly opened my door, like I didn’t even know who they were, and ran to Hubby {knowing he definitely watches his movies} and told him to get in the lift now because he could have a Kevin Hart moment. Alas it was too late. Apparently Kevin and The Rock are making a remake of the movie Jumanji in Hawaii. That will be cool.

Anyways, fast forward a few days and we’d made our way to Maui and were having a grand old time. I love Oprah. She’s the one person I’d LOVE to meet. I’m not crazy about celebrities, despite running into them regularly {Neil Patrick Harris, Mariah, Dawson, Orlando Bloom, and then Obama! Oh, and I DID make this wedding cake}. But I LOVE Oprah. I do.

So of course, when I was in Oahu Hawaii I had to ask where her house was there, and I had to ask the locals in Maui where her house was there. Not the exact address, but I wanted to know whereabouts and if anyone had ever seen her. I wanted to know if anyone had had an Oprah moment.

My new friend I met on the island HAD STOOD BEHIND HER AT THE DRUG STORE {pharmacy to us}. Can you imagine? I’ve tried to imagine, and I’m scared that I’d do something weird like smell her hair, or pass out. Yeah, weird.

On this one day we were making our way up to a crater, which is quite a long drive. We stopped for lunch at a little bistro in the Up Country, and while I was eating my chicken pesto panini I mentioned that Oprah probably lived somewhere near where we were.

“Well, let’s do a drive-by,” Hubby suggested, “I know you want to.”

Heck yeah, I wanted to… despite it being super creepy of me.

Her address isn’t generally known, but I consider myself to be as clever as a detective and I managed to find out {Google!} and we went on our way to find it.

Oprah owns a huge farm in the Up Country of Maui. It’s a lush and green area, about 40 minutes from the beach, and has a totally different climate to the coast. It’s cooler in temperature, and feels like a whole different part of the world. Oprah grows organic vegetables {100 varieties} which I hear she sources to restaurants around the island. I KNOW TOO MUCH. I do.

So, we did the drive by. Talk about highlight of MY LIFE.


{This is one of her gates. It has various cameras on them – see the one to the left on the tree thing? I think she was probably watching us be all weird. I kinda can’t believe I didn’t take more photos. I did share a few videos on Instagram Stories but forgot to save them. Dang!}

I saw a figure up near the main house {there are a few houses!}. A lady in black, with a black hoodie over her head talking to someone.

Oh man, I sound like SUCH a stalker. Don’t judge me. Please. {I know you’re judging me}.

Perhaps it was her, I don’t know. But HELLO OPRAH.

The kids were all like, “What are we doing? Why are we going slow? WHO IS OPRAH?”

I just told them to pipe-down because mummy was having a moment.

And then we went on our way to the crater. The crater was awesome, but I’m not sure how it compared to the Oprah moment.

Then… oh then… we were driving back down the mountain to get to our hotel, which was totally over the other side of the island, and Hubby decided to take a little back lane that was hardly big enough to fit two cars, and I wasn’t even thinking about Oprah… {to be honest I was thinking about Shave Ice} and a car started coming towards. A car that we knew to be the same as Oprah’s {but I’d totally forgotten because Shave Ice}… and Hubby said, “This looks like Oprah’s car” and because it was a small street we had to get real close to the car as it passed and IT WAS STEDMAN.

Stedman as in Oprah’s partner. We were like 1 metre away from him. I mean there was tonnes of metal between us with the cars and all, but STEDMAN.

I lost my mind {quietly, because Lulu was asleep} but STEDMAN.

I messaged my mum because she was the only person who knew who Stedman was, and even she was weird-ed out by my enthusiasm.

Later that night, Hubby asked me, “What would you honestly do if you ran into Oprah?”

I said, “I’d be cool. You wouldn’t know that I was losing my mind inside til she left. I’d just let her do her thing and be amazed that I was in her presence.”

“You SO would not,” he told me, “You would lose your mind!”

To be honest, I don’t know what I’d do, but I’d sure like to find out.

Also, I am weird.

Which famous person would you love to meet? And how would you react when you met them?

P.S. Oprah, I promise I’m not a stalker. Promise.

14 thoughts on “The Day I Went To Oprah’s House”

  1. Such an exciting fun story, although I am not a big Oprah fan. My big celebrity hero was always Paul Walker and sadly he died far too young. Oh and 2nd to him Vin Diesel other than those two, I am not big on celebrities.
    My son is a huge fan of Kevin Hart and Neil Patrick Harris ?Totally gets the humor

  2. I would be totally embarrassingly excited if I were to meet Eddie Vedder (pearl Jam). Have been crushing on him hard since I was a teenager!

  3. Such a fun story. I would totally do the drive by too. However I would try and keep who I was trying to stalk to myself otherwise my husband probably would not go along with it. Have been known to try and work out where Celebrities live – especially when in Hawaii – just in case I might casually meet them! lol Now I feel really silly posting this! lol

  4. Ooooh, I loved reading this, made me chuckle! I would probably do the same as you! I don’t think I’ve met any celebrities though. I’ve lived a sheltered life……..

  5. Haha, great story! How many of you want to tag this story on Oprah’s Facebook page…I defo do and if you get flown over to meet her (say, for an ultimate fan show) then I want to come as your guest lol!!!

  6. I adore this! I’m a crazy OPRAH fan, I totally get it. My very own (HA!) Oprah story is sharing too much, and given I’m a total over sharer – you are getting it any way! I was traveling with a friend, of a friend. We’d been to a mutual friends wedding in Portland, Oregon and took off on our own after the wedding for a NYC and Chicago adventure. While in Chicago we did High Tea at The Drake (because Oprah said it was THE place for High Tea in Chicago, so of course!) As with any extended travel you become close very quickly, even with those who you didn’t really know well before. AND the topic of many a conversation seems to steer toward your bowel movements. During the five week holiday together, we were all either “loose” or as one of the boys termed it “not farting with any confidence!” Or the opposite of loose, backed up and super uncomfortable. Jodes and I hadn’t been for days. I took off to the loo and had success. I returned to the table and told Jodie she had to go. Because clearly Oprah had sat on that toilet seat and, well Oprah would bring us comfort. She returned looking suitably comfortable, and announced she had used the same toilet as me, after spotting makeup packaging in the trash, I’d purchased earlier! So we concluded, that Oprah got us moving. Thank you Oprah.

  7. I made my brand new husband of one day walk along Hannalei Bay because that’s where George Clooney had walked . . . and found the house he stalked in the movie The Descendants . . and found the restaurant they go to in the movie . . . and we ended up driving down the road they drive down to get to their hotel every day. Did I mention I LOVE GEORGE CLOONEY?! And I love Oprah too, and I’d become a babbling idiot and cry and tell her we share a birthday if I ever met her.

  8. Great story. I’m sorry Chantelle, but it sounds like you’re a stalker! You know what car she drives??? I’d love to meet Jon Bon Jovi. I am a huge fan (probably at the same level as your Oprah worshipping level) and would probably faint if I ever got to meet him. I have loved him and the band Bon Jovi for 30 years, so to actually meet him would be a dream come true 🙂

  9. James Taylor, James Taylor, James Taylor. I want him to sing to me, just me. “How sweet it is to be loved by you”, “whenever I see your smiling face”. I would literally do the ugly cry.

  10. I love this. STEDMAN!!! that’s gold.

    I’d love to meet Oprah, still bummed that I had to give up my ticket to see her when she was here last year (I know you missed out too, so we can share our massive FOMO).
    I’ve been super lucky to have met quite a few celebs, there are heaps I love that i would rather not meet as I think it would spoil my adoration (I’m looking at you Madonna!), but if I had to pick someone to have a drink with it would be Lady Gaga. I find her intriguing and she’s so bloody talented it makes me cry.
    i think she is true to herself and stands up for her beliefs and I can easy say I would freak the F*** out if I was in her presence.

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