It’s Not the Destination, It’s the Companion. Or Is It?

You can find yourself in the most picture-perfect corner of the planet – turquoise water, trade winds, sunsets that look photoshopped by the Man Upstairs himself — but if you’re with the wrong person? Nightmare City, where every Mai Tai tastes like bitter regret.
 
On the other hand, you could be holed up in a sketchy Motel 6 off some anonymous highway in Bumfuck, Idaho, with an ice machine coughing up its last breath. And if you’re with the right person? Shangri-la with a minibar. You don’t need a view. You’ve got one sitting right across from you.
 
Which brings me to the question that was rattling around my brain for months: Was I prepared to spend seven days in one of my favorite places on God’s green earth with someone I haven’t seen in over forty-five years? A female friend I’ve known since first grade? 
 
For guidance, I did what any rational adult would do – I floated the idea past my friends. They warned me, gently, of course, with supportive language like, “Dave, what’re you, outta your fuckin’ mind?” Maybe. But there comes a time when you stop dipping your toe in the water and dive straight into the deep end of the unknown. And hope you don’t pull a Greg Louganis and crack your skull open on the sharp edge of the springboard.

First, the Destination

Maui is such a showoff. Obscenely beautiful. Breathtaking in that effortless, Oh this old thing? kind of way. The island has absolutely no shame about seducing you either. Slow at first, then all at once. I’m surprised it doesn’t have an OnlyFans account. If it did, I’d be financially ruined. 

This was my fifth trip to the Valley Isle, and by now you’d think the novelty might wear off. It doesn’t. Not even a little. Maui still hits me the way “Rocks Off” by The Rolling Stones does — familiar, but somehow better every time you hear it. 
 
We stayed on Kaanapali Beach, along the leeward side of the island. The calmer, sunnier side. Monica (stay tuned, you’ll hear all about her) had never been to Maui before, and for the uninitiated, Kaanapali is the perfect opening act. Gentle. Accessible. Just enough spectacle to make a first timer fall hard. 
 
The beach is wide, stitched together by resorts, tiki torches, and the low hum of vacation contentment. But it’s the horizon that steals the show. Look west and you’re staring into a living postcard. The island of Lanai to your left, Molokai holding court on your right. 
 
The sunsets? Forget it. The clouds roll, scatter, and reassemble across both islands like roadies working a light show, with every evening a different performance. That’s the moment you start to understand why people come here. And never leave.

Next, the Companion

Like I mentioned earlier, I’ve known Monica since first grade. St. Mary’s Elementary School in Waukesha, Wisconsin. Back when life was milk cartons, Man From U.N.C.L.E lunch pails, and nuns with radar for misbehavior. 
 
Funny thing is, I started life a long way from there. Born in Los Angeles at St. Vincent’s Hospital on a sweltering October Saturday. The day I was born the Santa Ana winds were marauding through the City of Angels like a pack of coked-up Hell’s Angels, which feels on-brand for my arrival. To this day I love those winds. They make everyone slightly twitchy, which I find oddly entertaining. 
 
But life has a way of rerouting you. Mine detoured hard when my father died of a heart attack at age 45, before I was old enough to remember him. And just like that, I was growing up in the Midwest…trying my best not to freeze solid.
 
But I digress.
 
Monica and I were both in Mrs. Howard’s first grade class. A matronly schoolmarm with cat-eye glasses and the de rigueur hairstyle of the day — the kind where women would shellac their tresses with Aqua Net and wrap them in toilet paper before going to bed. Laminated for durability, they would wake up with nary a hair out of place.
 
Although we were childhood chums, life did what life does. It drifted. And we didn’t have much contact after St. Mary’s. Middle school and high school came and went, leaving behind the usual debris of Stridex pads, baggies of stems and seeds passed around like sacrament, and all the other teenage rituals of the era. In high school we shared just enough orbit to keep the signal alive. After graduation I fled to college in San Diego and never looked back, chasing the radical notion that I might reinvent myself into someone who drank foreign beer.

An American Girl

A year later, Monica came out to San Diego looking for a change fresh off a bad breakup. “After all it was a great big world…” We were nineteen years old. She lived with me and my merry band of delightfully degenerate roommates for several months. Blame the ecosystem. Our apartment building was a full-time party already in progress. Basically Studio 54 with bad carpeting. It was more social experiment than student housing. 
 
After many tequila-fueled adventures both north and south of the border, Monica pivoted and landed a job at San Diego Bank. She settled nicely into her own furnished apartment — adulting before any of us had a word for it. Eventually she moved back to Wisconsin to marry her old flame. And just like that…poof. Another friendship lost to the wind.
 
Or so I thought. 

Next on Dave’s Maui Memoir: Part II – A divorce, a freak accident, and the domino effect that landed us on Maui.