Philip Galanes Will Interview Candace Bushnell, Erica Jong And Gail Sheehy At Hampton Library May 28 For Fridays At Five Kickoff

Some people do well one on one. Some thrive in group settings. Others, like Philip Galanes, are at their best in threes.

He attributes it to childhood conversations with his parents, he said. No matter the reason, his editor at The New York Times picked up on it and sent him into the field—in this case, a table set for him, actress Holland Taylor and politician Christine Quinn.

He was nervous. They weren’t. The conversation flowed. And the gold that came from it has lived as a monthly column known as “Table for Three” ever since.

One more chair will join the table on Sunday evening, May 28, when Mr. Galanes’s triangle morphs into a square, with himself and three distinguished authors—Candace Bushnell of “Sex and the City” fame, “Fear of Flying” author and feminist heroine Erica Jong, and Gail Sheehy of “Passages,” named one of the Library of Congress’s 10 most influential books.

Together, they will ring in the inaugural Fridays at Five kickoff event at the Hampton Library in Bridgehampton, in the same fashion as “Table for Three,” Mr. Galanes said.

“It’s turned out to be the luckiest gig in my career because it’s gotten me access to people that I never would have had dreamed that I’d have the chance to speak with,” the East Hampton part-timer said. “And often, the chemistry between the other two turns out to be so fascinating for me to watch and be a part of. I think it’s translated a lot to readers who actually get to see it through my eyes and feel like they’re speaking with these two amazing people, too.”

The list is long and the names varied, from senators, past presidents and brilliant business minds to actors, activists and supermodels, with nearly everyone in between. His tables have seen the likes of Barack Obama and Bryan Cranston, Brian Williams and Seth Meyers, Elton John and Darren Walker, and Arianna Huffington and Kobe Bryant, as well as local legends Dick Cavett and Alec Baldwin.

The general public is never privy to these conversations in real time. But for those attending Fridays at Five, they will be—as per a longtime tradition, according to curator and author Steven Gaines.

“The Fridays at Five series has been the premier literary series of the East End,” he said. “It was started nearly 40 years ago when the Hamptons was really a cradle for the arts and not a cradle for Citarella. It was born of a wonderful tradition. The Elaine Benson Gallery would have openings on Friday afternoons, and after people would stroll down through Bridgehampton to the library to see whatever local author was there—George Plimpton to E. L. Doctorow, you name it.”

These years were before Mr. Galanes’s time, but he’s attended enough talks to know how it goes, he said. As for how the format will work, he said time will tell.

“With a square, we’ll have to see. I have no idea. I’m still preparing,” he said. “I am always so over prepared. Even though I’ve been doing ‘Table’ for three years, I have no faith that they will ever come together until I’m leaving the lunch with the taped conversation in my pocket. I go in really over prepared, but the key is to try to be open enough to listen to what the participants are saying and try to follow that, too. I can’t be too programmatic and force what I’m going to talk about on these amazingly accomplished people. Often I have to have a seed of an idea, or we’d just have an hour of small talk and be on our way.”

As with the majority of his interviewees, Mr. Galanes has not met these three authors prior to the conversation. That is enough to set his butterflies into overdrive, he said.

“I am always nervous, every single time. Always,” he said. “And I think that’s just a personality thing. I’ve done something like 50 of them for The Times now and you’d think that would translate to some kind of confidence, that you can pull off the 51st one. But I’m as nervous today as I was that first day, and, sadly, I think I will be just as nervous as the day when The Times cuts me loose.”

A kickoff event for Fridays at Five, featuring Candace Bushnell, Erica Jong and Gail Sheehy in conversation with Philip Galanes, will be held on Sunday, May 28, at 6 p.m. at the Hampton Library in Bridgehampton. Admission is $25. The series will begin July 7 with Jay McInerney, followed by Kate Siegel with Kim Friedman on July 14, Blanche Wiesen Cook on July 21, Colson Whitehead on July 28, Kati Marton on August 4, Ina Garten with Rob Marshall on August 11, Marshall Watson on August 18, and Carl Bernstein on August 25. For more information, call 631-537-0015, or visit hamptonlibrary.com.