Photo: Illustration by Kikuo Johnson/New York Magazine

With the sun on my face, I stand by the side of the road, a small bag of pastries from the doughnut shop in hand, for my first hitch of the season. I’m off to a rocky start; there’s been no action for the past half-hour. A car approaches (okay, here we go) … My thumb goes out … The guy is balding, with glasses …

But wait—I recognize this guy from pictures in magazines. In fact, didn’t I just read some brilliant piece written by him in the New York Times? Yes, somehow my nascent psychic powers have manifested the actor, comedian, writer, and fellow Homo sapien Larry David.

This is not a fantasy; it actually took place, Larry David picking me up and driving me across Martha’s Vineyard one summer day. The conversation that follows was recollected from memory, then later looked over by Larry, who confirmed it, then remarked, “If I’d only known, I would have been wittier.”

Larry David: Need a ride?

Paul Dolman: Yes. Thank you.

L.D.: You’re not a serial killer or something, are you?

P.D.: Well, it’s the summer, and we are on the Vineyard, so even if I was, I’m on vacation and not working.

L.D.: [Laughs] Where are you going?

P.D.: To be honest, I’m not really sure. How about Aquinnah?

Larry jolts backward.

L.D.: That’s the farthest point of the island!

P.D.: Hey, take me as far as you like. I can always get another ride.

L.D.: Well, why the hell not. It’s a beautiful day. You know, I never pick up hitchhikers.

P.D.: Really?

L.D.: Well, it’s usually a bit awkward, and you never know what or who you’re going to encounter.

P.D.: So you’ve never picked anyone up before?

L.D.: I once stopped to pick up a girl, and then there was this creepy-looking guy standing behind the bushes waiting to jump out and get in, too. So I just quickly drove away.

P.D.: Sounds like the old hitchhiking double-cross.

L.D.: Is that what they call it?

P.D.: It’s a trick a lot of amateurs use. That’s something a pro would never try.

L.D.: Have you ever pulled that one?

P.D.: A few times early in my career. But no one ever drove off like you did.

L.D.: I was surprised; it felt a little tricky.

P.D.: Most of the time when that happens to the driver, they are pretty pissed off. So the ride can be weird and awkward.

L.D.: Is this hitchhiking thing something you do a lot?

P.D.: Actually, today was the first time in I don’t know how long that I’ve stuck out my thumb.

L.D.: Lucky me.

P.D.: Yesterday I rode my bike for about 40 miles, and now my legs are killing me. I promised some friends I would meet them up at the beach, so I had no choice.

L.D.: Don’t you have a car?

P.D.: I could use my parents’ car, but my father probably wouldn’t like that.

L.D.: You’re living at home?

P.D.: Just visiting indefinitely. I’m probably only staying a week or two. I’m sure my dad will run me off after that.

L.D.: The old guy is pretty tough?

P.D.:He wasn’t always like that, but man, the last 30 years … Hey, why did you pick up me?

Larry doesn’t answer for a moment or two; he just stares ahead as we wind our way slowly up the island.

L.D.: I really don’t know. I just felt like I was supposed to.

P.D.: That’s pretty deep.

L.D.: Now, don’t get too heavy on me; we still have a long way to go here. By the way, are you Jewish?

P.D.: Are you?

Larry shoots me a look like, Are you kidding?

P.D.: I think my actual lineage is mongrel.

L.D.: Mongrel?

P.D.: My mom is a disenchanted Irish Catholic, and Dad’s lineage is all over the map—Germany, Austria, Odessa, Russia … When I look up my family tree, most of my recent ancestors still have tails. Actually, Mom grew up in Queens; Dad was from Brooklyn, and yes, his heritage is Jewish.

L.D.: Brooklyn? That’s where I was born. Do you know where he grew up?

P.D.: I think it was very close to Ebbets Field.

L.D.: I grew up in Sheepshead Bay! Was he a fan of the old Brooklyn Dodgers?

P.D.: He lived and died with them.

L.D.: Did you talk about those times much?

P.D.: We used to be able to connect, but as I got older …

L.D.: That can be a generational thing. Do you live in New York?

P.D.: No, Nashville.

L.D.: You don’t strike me as a Nashville guy. No you-alls … Did you grow up in the South, and how did you end up here?

P.D.: Actually, yes and no. I grew up in South Florida, but we spent some vacations here at the Vineyard when I was a kid. Later on, I started coming here and getting summer jobs doing a variety of things. I worked in a bike store, I drove a cab, and for years I played the piano.

L.D.: You should live in New York.

P.D.: I should?

L.D.: Yes, you should.

P.D.: Big cities have always felt tough for me. The energy is great, but I need more trees than concrete. And there’s not enough sun.

L.D.: I’m thinking New York would be good for you.

P.D.: Okay, I’ll have to check into that.

L.D.: I love it here, too.

P.D.: It is easy to love. How long do you stay?

L.D.: I try to stay the whole summer, though I have to leave now and again. My kids are here, so it works out well—it’s a good place for us to spend time together.

P.D.: Do you like being a dad?

L.D.: You know, you ask an awful lot of questions.

P.D.: I guess I’m just curious.

L.D.: That’s a nice way to put it. But yes. It’s a lot more fun now that they are older, and they’re these wonderful people you love to be around.

P.D.: I imagine they grow up fast.

L.D.: You have no idea.

P.D.: What do you do here all summer?

L.D.: Work on my show, play some golf, and see my kids. What about you?

P.D.: Ride my bike, eat a lot, swim, write in my journal.

L.D.: Are you a writer?

P.D.: I write stuff down, but I’ve never really written anything substantial. I published a book once, a collection of interviews with people.

L.D.: So you like to ask a lot of questions. I see a disturbing trend here.

P.D.: Do you write every day?

Larry gives a slight grimace.

L.D.: No, because on my show, I wear several hats. I have to divide up the time between writing and the other stuff.

P.D.: Do you love to write?

L.D.: I wouldn’t say that. It’s a lot of work.

P.D.: Have you ever felt lost?

L.D.: Yes, of course.

P.D.: I feel like I’ve somehow ended up off the beaten path.

L.D.: That’s not always a bad thing. Sometimes you have to wander a bit, and do what you don’t want to in order to figure out what it is you’re supposed to do. What brought you here?

P.D.: If I’m honest, I’m trying to get over a girl.

L.D.: Were you married?

P.D.: No. I thought about it with her but was afraid to commit. I wasn’t sure.

L.D.: Did she drop you?

P.D.: It kind of just drifted and descended until it crashed. I thought being on the Vineyard would help.

L.D.: Relationships are tough.

P.D.: Are you married?

L.D.: No, divorced.

P.D.: Oh, I’m sorry.

L.D.: It’s been a couple of years. The hardest part is over.

P.D.: The beginning is the worst.

L.D.: It is.

We pass a gray-haired guy in a jeep who looks a lot like Ted Danson.

P.D.: Hey, do you know Ted Danson?

L.D.: Yes, he’s a very good friend. He’s been on my show, too. Have you seen it?

P.D.: The show, or the one with Ted?

L.D.: Either.

P.D.: Uh, well … No, I can’t say I ever have … ever seen that one with Ted.

L.D.: But you have seen the show, right?

P.D.: Um … which one?

L.D.: Either one. You’ve seen … Wait a minute …

P.D.: Okay, first of all, I am not a TV guy.

L.D.: You mean …

P.D.: I’m probably one of five people on the planet who hasn’t seen Seinfeld.

L.D.: What?

P.D.: And I haven’t seen your new one, either.

L.D.: My new one? It’s about to start its seventh season!

P.D.: Oh? Congratulations!

L.D.: Are you saying you have never seen either of my shows? Not even Seinfeld?

P.D.: Don’t take it personally. I get all my culture from books and magazines.

L.D.: Do you watch movies?

P.D.: Of course.

L.D.: Do you rent DVDs?

P.D.: Yes, I rent DVDs.

L.D.: Then why not get my shows on DVD?

P.D.: I guess I could do that.

L.D.: After all, why would you deny yourself so much pleasure?

P.D.: Okay, you win. I’ll tell you what: I’ll watch your show in exchange for this ride. Deal?

L.D.: Okay then, we have a deal.

I hold out my hand and we shake.

P.D.: Here’s some irony for you. I can’t get my parents to watch the sunset because they’d rather watch your reruns.

L.D.: Really?

P.D.: Yes, they pass on the sunset.

L.D.: Well, seen one, seen ’em all.

P.D.: But you have to enjoy the island’s natural beauty.

L.D.: In a way—but no, not really. I need to be on drugs to connect with nature.

P.D.: That’s funny. Hey, what’s it feel like to have a lot of money?

L.D.: Most days I don’t even think about it. But it’s better to have it than not. Money can’t make you happy, but it can make you happier.

P.D.: Did success help make you happy?

L.D.: Who said I was happy?

P.D.: Why do you think you were successful?

L.D.: I got lucky. I found a partner that the public happened to like.

P.D.: Jerry?

L.D.: He was the perfect person to relay my brand of comedy. I’m not sure I would have had the success I had without that.

P.D.: So luck was huge.

L.D.: Luck always plays a part for everyone, whether they want to admit it or not. I was very lucky, and I know it.

P.D.: What brings you the most satisfaction?

L.D.: That’s a tough one … I guess it’s when I discover a really great idea and start developing it.

P.D.: That’s number one?

L.D.: And making a woman laugh. What is that about? And the prettier the woman, the more satisfaction I get. It doesn’t make any sense, but I’m being honest.

P.D.: What’s it like to make it really big?

L.D.: Who said I made it big?

P.D.: That’s true, it’s only television.

L.D.: Very funny. Remember, you still have a very long way to Aquinnah if the ride ends here.

P.D.: Seriously, though …

L.D.: The whole process is a hard thing to describe. To me, it feels kind of surreal.

P.D.: Even after all this time?

L.D.: I’m not sure it ever completely sinks in. So much changes, and yet nothing really does … You would like to think that you don’t change, but I am sure in a lot of ways, you do.

P.D.: Wow, this is really a magical ride.

L.D.: Maybe for you.

We pass the old Chilmark store—an excellent spot for pizza.

P.D.: Hey, why don’t we have lunch sometime? My treat.

L.D.: No. Hey, wait a minute; you claim you’ve never seen my shows. Right? How did you know who I was?

P.D.: I’ve seen your picture in magazines and on websites. You did a great thing in the New York Times recently that was hysterical. Also my younger brother is a huge fan of your new show.

L.D.: Curb Your Enthusiasm.

P.D.: He’s been telling me to watch it for years.

L.D.: It’s a lot of work to put something together. People have no idea how much energy and time is involved.

P.D.: Do you believe in a higher power or universal intelligence?

L.D.: Oh, God, yes! I mean, you have to believe in something higher and wiser. Especially when you look at this … [Sweeps his hand across the vista.] I mean, look at this landscape.

P.D.: It’s so miraculous.

L.D.: And how perfect it is. I’m not sure what it is, but there’s definitely something.

Larry pulls over to let me out. I gather my backpack.

P.D.: Thank you. Hey, I still think we should go to lunch.

L.D.: Absolutely not! Now get out of here. Who knows, I’ll probably see you around.

P.D.: I really enjoyed the ride.

L.D.: Me too. Now get out.

Adapted from Hitchhiking With Larry David, by Paul Samuel Dolman. Published by arrangement with Gotham Books/Penguin Group (USA). © Paul Samuel Dolman, 2013.

*This article originally appeared in the June 3, 2013 issue of New York Magazine.