Hitchhiker’s Guide to The Hamptons

The sight of the two women planing their thumbs along the Amagansett beach road took a few moments to register.

I had not seen a hitchhiker in some 20 years. This was partly a function of having moved from the Midwest to the city, but I also think that the notion of hitchhiking as an adventurous, even romantic mode of travel probably died with the 70′s. Sure, hitchhiking was a gamble, for both the rider and the driver, but the odds seemed somehow better that something memorable would come of it. Back then, hitchhikers were sexy catalysts in songs and stories. There’s the Eagles’ “Take It Easy,” Sammy Johns’ “Chevy Van” or just about any issue of Penthouse , for that matter.

But as both Woody and Arlo Guthrie faded from our consciousness and we became a more suspicious and isolated culture, hitchhikers pretty much became equated with serial killers. They were the kind of people who would tie Jennifer Jason Leigh to two semitrailers at a truck stop so that she would be drawn and quartered when the two trucks pulled away.

I was not interested in either of the above scenarios when I slowed down next to the women. I was looking for a random social encounter.

Covering the party beat in a place as financially exclusive as the Hamptons involves following a largely finite group of people as they traipse through the same flight of parties and benefits weekend after weekend. Because everyone knows everyone else, the familiarity takes its toll. A kind of social dysphasia occurs, wherein conversation becomes stilted, superficial and essentially meaningless until Labor Day, when the Manhattan social circuit warms up and things become a lot more tolerable.

I had just departed one of these Hamptons events, and seeing the women flailing their arms, I thought: Here is an opportunity to leaven my boredom. As I pulled up next to them, I quickly scanned the women’s faces to determine that they were not shifty-eyed. Sufficiently convinced that they were not packing heat, I motored down the window and asked them where they were going.

“To 27th Street,” said the dark-haired Asian woman with the trendy thick eyeglass frames and the Oxford accent. She had obviously meant Route 27, the main drag of the Hamptons, which was really only half a mile away. This was heartening. An indication that these women were really strangers to the Hamptons.

The other woman, a scrub-faced strawberry blonde with a pageboy who looked like her name should have been Scout was saying something, too. In retrospect, I think she was saying, about her friend, “She doesn’t know what she’s talking about,” but I wasn’t really paying attention. I had already told them to get in.

Scout got in the front seat, and the Asian woman, I believe she introduced herself as Ni, got into the back. I wanted to ask Ni if the Monty Python comedy troupe had anything to do with her name, but she looked too young to know who Michael Palin and John Cleese were. Besides, I could sense Scout’s eyes scoping out the interior of the car I was driving-a 1997 green Bonneville ( Meee-ow! )-before they settled somewhere behind my head.

“Lookin’ for a hot date tonight?” Scout said.

I almost swerved off the road, but then I realized that Scout was making fun of the cream-colored blazer that was swinging, in bourgeois fashion, from a plastic hanger attached to a hook behind my seat.

“No,” I blurted out, then … nothing. Scout had flustered me. And while my mind was doing the old humina-humina, she followed through.

“Uptight?” Scout said in a disconnected way, as if she wasn’t even addressing me. It was like that old trick for dumb high school assemblies where you pretended to cough loudly into your cupped hands but in reality were yelling “bite me” or some similarly hostile phrase into the buzz of the auditorium.

It felt as though Scout’s comment had negated the effects of the Bonneville’s air conditioner. I looked into the rearview mirror to see if Ni was reacting to any of this. She was looking out the window, probably searching for a sign that said 27th Street.

Instead of a random social encounter, I was enduring some random needling, courtesy of the obviously whip-smart (emphasis on whip) Scout. At least she’s not boring, I thought to myself.

With the blood still pooling in my cheeks, I managed to explain that the jacket was there because I was a newspaper reporter who covered a lot of social events out in the Hamptons. The jacket was necessary.

That’s when things really went downhill.

“What paper do you work for?” she asked.

When I told her, I expected Scout to move on to another subject. She didn’t.

“I know an editor there,” Scout said. “There’s a guy there named P– that I know. P–, P–, what’s his name.”

Scout, it turned out, knew my boss. She was the ex-girlfriend (and I have to admit I can see why) of a good friend of his.

That was it. I would have rather endured another half-hour of Scout’s goading than to have heard this. My random social encounter didn’t seem random anymore. I didn’t know Scout, but she and I both had the acquaintance of someone in common. On the graph of my inescapably linear life, I could now draw a dotted line from me to my boss to Scout.

This depressed me as I pulled into the parking lot near where Scout and Ni had asked me to drop them off. It seems rare these days that I meet someone whose social world has nothing to do with mine. I find that amazing, given that I live in the largest metropolitan area in the country. Maybe I’ve got to get out of town more.

The women were going to an art exhibit opening and they asked me if I wanted to join them. I didn’t think about it too long before I told them No. I couldn’t bear walking into another room that was peppered with people I knew.

My next destination was west, in East Hampton, but as I pulled out of the parking lot I headed east, toward Napeague. The roads aren’t so crowded there. The houses aren’t so close together. And at night when the sand dunes sparkle in the headlights and ocean mist blows over the Montauk Highway, the world seems a much bigger, less familiar place.