Maui Surfer Girls Teaches Cher! - Maui Surfer Girls
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Maui Surfer Girls Teaches Cher!

Teaching Cher yesterday was the most memorable surf lesson in my ten years of teaching.  To top off my birthday weekend, I had the privilege of spending the morning with her on a stand up board and the afternoon soaking in her infinity pool and jacuzzi back at her gorgeous vacation rental in Wailea. I had to pinch myself all day!

I met Cher back in 2002 when I taught her 7 year old god son how to surf.  We work with a concierge desk that manages exclusive vacation rentals and referred Maui Surfer Girls to Cher’s personal assistant.   Throughout the years, I’ve coached her god son and I was impressed to reconnect with him again now as a handsome, gun-ho 15 year old.  During their recent visit, Cher request me to teach her how to stand up surf.

Meeting Cher at the beach yesterday was both exciting and overwhelming.   As she approached me in her black long sleeve rash guard and black lycra leggings, I held out my hand to greet her like any other student I’ve taught.  She shook my hand, and opened her arms to hug me.  Right away I felt at home with her and I think I even said, “It’s great to see you again Cher.”  Reminding both herself and me that yes, in fact, we go back to 2002 — we’re homies now 😉  I offered her spears of pineapple that I prepared and we talked about her god son’s surfing progress.

For the next half hour I gave Cher and her personal assistant a land lesson, which I tried to make concise and entertaining.  I noticed that the wind was building and learning SUP is challenging in the wind.  After all, I was in charge of Cher’s well being in the ocean and like any other student, I take that job very seriously.  I felt honored that she trusted me enough to keep her safe out there.

I told her, “If you can dance on 5 inch stilettos, then balancing on a stand up board will be a piece of cake for you!”  She laughed and I think that lightened the air of anxiety I felt from her.  She practiced popping up to her feet on the beach and I could tell she was going to do just fine out there.  For 64, she’s in phenomenal shape!

We did some stretching, talked about the importance of yoga, and then charged through the choppy conditions with our SUP boards in tow.  After the first 5 minutes on the water she looked over at me and said, “This is not as frightening as I thought it was going to be.”  I told her that the ocean can be a great place to find peace and joy.  Slowly I had her stand up to her feet.  The choppy conditions kept throwing off her balance and most people would’ve thrown in the towel.  I was so impressed with her tenacity to keep her balance on the board.  She’d fall and get right back up on the board to try it again.  We spoke of her being a Taurus, and bull headed in life.  No wonder she’s had such a long legacy of success – she’s not one to quit when the going gets tough or in this case when the surf gets rough.

An hour into the lesson we drifted down the beach.  She sat up on her board and talked candidly about her new movie Burlesque, what Maui and Oahu was like in the 50s, what I though about the island of Kauai…she recalled her days roller skating with some of the original hard core roller derby girls, after hearing about my weekend of roller derby and karaoke singing (which she’s apparently frightened by).  I asked her to guess my age after telling her it was my birthday this weekend.  She guessed 32.  I took that as a compliment coming from Cher – so timeless and active at 64.  She mentioned that 40 was the best year of her life. A number that I dread turning in 3 years, she gave me some hope that it might not be so bad.

Just as I started to really relax and enjoy our conversation, a wave picked up Cher’s stand up board and started surfing her sideways and backwards towards shore. She got pretty pummeled on the beach.  My heart missed a beat and I yelled over to her, “Are you OK?”  She popped up to her feet quickly reassuring me that she was fine.  It was time to call the lesson – I didn’t want the responsibility of a tired Cher on a 12 foot board in 20 knot gusty trade winds.

We walked back to our place on the beach, where my dog “Luna” laid patiently under a Kiawe tree — she was obviously on her best behavior for Cher thank god!  We ate some more pineapple and continued our conversations.  I asked her if she was comfortable giving MSG a testimonial and picture.  She denied the photo but said she’d give us a testimonial.  Much to my surprise, Cher invited myself, my two lovely assistants, Jen and Stephanie, and the adorable Luna, up to her property across the street.

We soaked in her jacuzzi, in the middle of an amazing infinity pool overlooking the ocean.  For about an hour we relaxed at the poolside and kitchen area.  Cher’s god son had a guitar, which Stephanie strummed on and sang a couple beautiful songs.  Cher was in her room looking over the brochure I gave her about our girls surf camp while writing a testimonial about her experience today with us.

On the back of an envelope she wrote:

“I haven’t had so much fun in the water in years!  It made leaving Maui even harder! –Cher

PS  Dustin Rocks!

But truly Cher rocks!  And she rocked my surf instruction career that day — a day I will never forget!  I am forever grateful to Cher for opening her home, her heart, and her mind — entrusting her body to experience the ocean on a stand up board with the Maui Surfer Girls.

Cher Maui - Cher Signature - Cher's testimonial

Cher’s testimonial on the back of my medical insurance envelop (ironic or idiotic that I couldn’t find any other paper to write her testimonial on 😉 Cher Maui | Maui Celebrities 



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9 Responses to “Maui Surfer Girls Teaches Cher!”

  1. ingrid

    What an awesome story. Yes, Cher is right, Dustin rocks!

  2. Anastasia

    Great story! Thank you!

  3. cherme

    Wow! So awesome!
    Cher rocks!

  4. bettyann

    Great story!!! Thank you for Chering!!!! Lucky you!

  5. bettyann

    BTW…when was your birthday? Mine was 3/29–talk about dreading a number…mine is 50…eeeeeekkkkkkk!!!!

  6. Janet Wilson

    Wow, how lucky are you? To be able to teach Cher, then chat to her and just chill out with such an incredible icon and amazing person must have been the experience of a lifetime and one you will remember forever. Jan UK

  7. cher_goddess

    I absolutely loved reading your blog about your day with Cher. It’s rare to get such an inside look at Cher’s life and activities — and what a treat to see her testimonial in her own handwriting!
    Truly, thank you for sharing.
    I tweet all about Cher news on twitter – you can find me at @cher_goddess.

  8. meghan

    i got the link to this off of thats sooo cool that you got to teach cher!

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