Someone’s been sleeping in my bed

June 2009

By David Roper

The most embarrassing thing that has ever happened to you? Go ahead, name it. But you won’t top this:

Actually, the absolute King of All Embarrassing Moments was witnessed not by me, but by my boss the year I was the captain of his 58-foot wooden schooner in Marblehead. But first, a little about him and the vessel. He was a great guy, but above all he was probably the most unflappable man I ever met. I remember him vividly, sitting casually at the helm of his great schooner, engaged intently in conversation with several guests, a gin and tonic in one hand, a couple of fingers of the other resting on a spoke of the big teak wheel, all while taking this huge vessel with her long bowsprit all the way to the head of crowded, tiny Manchester Harbor.

I was his “captain,” but he was the owner, so I simply crouched quietly by the bitts at the bow, bit my tongue and held my breath, as the 10-foot bowsprit whisked past the sterns and bows of several moored boats, missing each and every one by only inches. No one was ever sure if my boss just had an uncanny sense of the control of his big yacht, or he was just plum lucky every time. But he always missed.

He seemed such a carefree man, living for the moment, and never the moment after. One day, back on the mooring, as he looked down into the engine room, he said, “Say, Chief, why don’t you give that big-old engine a coat of paint tomorrow. It’s all gray and black and greasy. And paint it white this time so it’s really shiny.”

When I replied that that was fine, but it would take two days to do it and he’d miss an extra sailing day, he asked me why the two days. I replied that it would take me one day of prep to degrease and scrape it, and one day to paint. “I don’t want to miss two days of sailing,” he said. “What will happen if you just paint it, just spray the thing white, nice and thick and pretty?”

Well, I told him, the paint will fall off. “How soon?” he asked. I told him I didn’t know how soon, but eventually it would.

“Eventually? What’s eventually? Everything that happens happens eventually. No, just paint it,” he said emphatically. “I’ll probably be dead before the paint comes off anyway, and this way I won’t miss an extra day of sailing.”

Anyway, you get the idea about this unflappable man and his living for the moment. Which brings me back to that really, really embarrassing, award-winning moment. I’ll set the scene: My boss lived in a huge house right next-door to one of the big yacht clubs in Marblehead. It had a long front porch, great foyer with ship models, and a big, winding staircase leading up to the second floor, where the hallway led to several bedrooms, including the guest room. In fact, it was very similar to the front entrance area of the yacht club next door.

One summer an out-of-town couple came to visit friends who were members of this club. The hosts had arranged for the couple to stay in one of the hotel rooms at the yacht club. That evening, they all had dinner and drinks at the host’s house, and when the evening wound down, the visitors asked for directions to the yacht club, which was only a quarter-mile away.

The hosts offered to take them and show them the way in, but the guests declined, saying it was late, too much trouble, and they could find their way easily enough. The hosts gave them the simple street directions, detailed the yacht club’s entrance, the ship models, the foyer and the staircase. “The rooms aren’t numbered,” they said, but just go in the front, up the staircase, and your room is the first door on the right.”

The visitors said they would be fine, got in their rental car, and headed for the yacht club. Though they followed directions carefully, they didn’t get it quite right, and instead entered my boss’s house, where everyone was asleep, but the big front porch and foyer were well lit and the front door not locked.

Quietly, suitcases in hand, they made their way up the stairs and opened the door to the first room on the right. It was a nicely made-up guestroom, and, like Goldilocks, they fell into a bed that was just right, and they had a lovely sleep. In the morning, they made their way downstairs, suitcases in hand, and into the foyer.

Looking around, they spied a man (my boss) sitting alone at a large table in a large dining room adjacent to the foyer. His housekeeper, dressed in white, was serving him something. “Excuse me, is this where we sit to get some breakfast?” the wife of the couple asked, putting down her suitcase.

My boss looked up from his breakfast, cocked his head, studied the two as one might look at a wild new abstract painting, took a sip of his coffee, and said: “Well, I don’t know who you are, or what you’re doing in my house, but what the hell, since you’re here, you might as well sit down and have some grub.”

Go ahead, top that moment. I dare you.

Dave Roper sails out of Marblehead, Mass.