09/19/2011 12:30 pm ET Updated Dec 06, 2017

I Don't Regret Losing My Surfing Virginity To The Maldives

"Paddle a bit faster."

This is the sage advice from Chris Prewitt, my surf guru, as a wave is about to have its way with me. I'm in good hands. Chris, a former competitive surfer and global wave-chaser, possesses a commanding calmness and gobs of patience, both helpful virtues for hand-holding newbies. A moment ago, as I sat on my board, bobbing up and down, Chris reminded me of skills we practiced in the lagoon sessions: popping up and staying up.

While in the lagoon, I was desperate to meet a real wave. Now that I'm faced with the reality of imminent waves, I yearn for the calm waters of the lagoon and more time to perfect my pop up. But alas, the moment is upon me. Time to perform or fail.

I've come to the Maldives to achieve one of my lifelong goals, learning to surf. I'd tried surfing with friends but their amorphous tips produced nothing but near-drownings and a complete sense of failure. This time I opted for true experts. The Four Seasons at Kuda Huraa and its partner Tropic Surf , an impressive luxury surf operation, offer a 4-day Surf's Up package for beginners. Clearly they've been down this road before.

I was elated when, earlier in the morning, I learned that we were heading to Tombstones. As a 40-year old surfing virgin, I am clearly playing catch up and I needed a name like Tombstones to mark my arrival to the sport and impress friends and family. (Should I mention that at some point we playfully renamed the break "Kitten's Kisses?" Probably not.) When we actually arrived at Tombstones, the elation vanished, replaced by a significantly elevated heart rate, an increasingly dry mouth and a creeping sense of fear. Such is the way of firsts.

Take two. "Hands. Back foot. Press up." I hear Chris, but I'm having trouble turning his words into actions. I know where my various body parts belong but things are happening way too quickly and my brain can't keep up. Instead, instinct kicks in. As the wave lifts the back of my board, my mind goes dark, I simply try to stand...and down I go again.

Surfing is a misnomer. With most activities, the name reflects the main action involved. (For instance, swimming involves mostly swimming.) The same is not true of surfing. A more accurate name would be paddle-to-surfing. To get to the waves, I have to paddle out. As I sit and wait for a wave, I have to paddle around to adjust for water currents and wave shape. Finally, I have to paddle in to the wave. The result of all this paddling; bruised ribs, chaffed nipples and a cramped neck. This is all pre-surfing. I don't recall this much effort in pursuit of my other firsts.

Take three. Not even close, I miss the wave entirely. More paddling.

A few days prior, I watched world champions compete in the inaugural Four Seasons Resorts Maldives Surfing Champions event. As Mark Occhilupo, Josh Constable and others skimmed effortlessly over water, popped up as swiftly as jacks-in-the-box and maneuvered along waves as if taking a morning stroll, I thought, this looks easy. It's not.

Take four. Chris and I make one adjustment. We decide that I need to stop looking down at my board. We spot a boat in the distance. To guarantee it as my focal point, we decide to fill the boat with a bevvy of bikini-clad women. Chris' last words, "Look Up." I forget about the recent series of failures and the various board-related rashes and bruises and, instead, lock my gaze on a boat full of imaginary women. And I'm up. Standing and gliding along the surface of fast moving water.

Did I have the wave or did the wave have me? It didn't matter: I'd found the sweet spot. Then, in a flash, it was over.

In surfing, the first ride doesn't quite mark the end of the first time. In this particular case, my first challenge is already upon me; a combination of frothy, churning whitewater, the aftermath of a wave, and board misbehavior. Being tethered to a board by an ankle leash sounds sort of kinky but it simply makes me an unwilling participant in the board's physics. I've stopped but my board continues its progression forward. I eventually prevail in the tug of war and we reunite only to be immediately faced with my second challenge; angry relatives. Waves typically show up in multiples or 'sets'. To me they seem more like loyal family members lashing out for obvious reasons. Fortunately, the lagoon sessions are paying dividends, and I use the 'eskimo roll' (essentially flipping the board and hiding under it) followed by a 'headlock' (grabbing the nose of the board and holding on for dear life).

With my graduation to surfer status, things start to click and I caught a few more rides. At some point, my enthusiasm succumbed to my utter exhaustion. Unable to hold up my neck, I paddled flat-faced on the board towards the boat. Then, in a true Disney moment (and I'm not making this up) I found myself surrounded by a pod of 40 to 50 dolphins, some leaping and spinning through the air. Either they think I'm really good or I'm really lucky. Either way, I reveled in the moment and in my decision to catch my first waves in the Maldives.