KEY WEST BACK IN THE DAY: THE CRYING MAILMAN & DATING DISASTERS

Key West’s Bahama House, captured in a classic postcard image, delights bike riders and pedestrians who pass by the history-rich Old Town home. DeWOLFE AND WOOD COLLECTION/Florida Keys History Center

Lately my female friends have been sharing tales of contemporary dating, from the joys of new love to romantic disasters — which, for me, triggered memories of dating in the 1970s and early ’80s. 

It was a different era then, when romance was casual and people were frequent victims of “lust at first sight.” I once fell for a handsome pirate over cocktails and took him home to share a bubble bath — which began a five-year relationship. 

He opened my eyes to the freewheeling Key West and its resident outlaws, who scorned “real-world” rules and lived by their own personal code. He taught me to enjoy simple living, value the stories told by vagabond shrimpers and poets, and share his unconditional love for the island. 

By the time we drifted apart, his strong principles and passion for Key West had changed my life.  

Some of my female friends, however, had far less inspirational boyfriends. 

One dated a fishing captain we’ll call Johnny. Bearded and boyish, he was an expert at his job.  

Yet when he wasn’t spotting fish for charter clients, Johnny was basically clueless. That became clear one day when, unable to reach his girlfriend, he called me in a panic. 

“I’m cleaning my bathtub,” he said in a faint voice unlike his usual confident tone. “My bathroom doesn’t have any windows, and the bleach I was using didn’t work, so I tried one of those strong cleansers –” 

His explanation was interrupted by a fit of frenzied coughing. 

“Hold on,” I said when he recovered. “You used bleach AND strong cleanser? In a room without a window?”

He muttered an assent.

“Johnny, get the hell out of that bathroom!” I yelled. “Combining those two things is practically lethal!”

“Yeah, it kind of feels like I made a poison gas,” he said weakly, while I considered calling the nearest Hazmat team. 

Yet despite his ineptitude, Johnny was a better boyfriend candidate than the crying mailman. 

The crying mailman, unfortunately, was one of my dates. Several months after I ended things with my pirate, a mailman I knew slightly asked me out. He was gentle, funny and seemingly sane. So I said yes.   

This 1970s aerial of the Pier House Motel shows the restaurant and bar area at right, with the accommodations at left and the beach between them. DALE McDONALD COLLECTION/Florida Keys History Center

We would go to dinner, he said, at the waterfront restaurant at the Pier House Motel. The restaurant was famed for its island-style sophistication and white conch chowder (which could cure hangovers, ease cold symptoms and probably end minor wars).

The mailman arrived at my William Street cottage with flowers and a bottle of wine. While I put the flowers in water, he opened the wine — and drank the entire bottle in 20 minutes. This was a bit concerning, but I figured maybe he was nervous.

We rode our bicycles to the Pier House in the post-sunset dark, along narrow streets where night-blooming flowers perfumed the air and lights shone from the windows of Victorian homes. Biking through the lovely, shabby Old Town neighborhood always warmed my heart, so I ignored my concerns and enjoyed it.

That was a mistake — quickly proven when, after sitting down at our restaurant table, the mailman ordered a large cocktail and burst into tears. 

Unnerved, I asked what was wrong. 

“You’re so beautiful,” he sobbed. “Your beauty is making me cry.”

Even on a good day, I wasn’t beautiful. Quickly revising my earlier estimate of my date’s sanity, I realized the situation had become a little scary — and could only get worse. So I made up an excuse and fled.

He must have dried his tears eventually, and somehow we never ran into each other again. But it took many months before I stopped flinching reflexively at the sight of a mail carrier’s truck.  

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