Sleepless in Seattle, with its reliance on snail mail and radio shows, and its dearth of sex scenes, is not a movie that would get made today, according to those who worked on it in 1993. Appearing at the YMCA’s annual Stars and Stripes fundraiser Tuesday night, the film’s lead actor Meg Ryan said she hadn’t seen the movie since the premiere, so her daughter read her the online summary earlier that day as a refresher.

“I was listening and going, how could that possibly work? How could you actually pitch that to any executive anywhere?” she said, laughing. “How do you get away with a romance where the people have two scenes together?”

Ms. Ryan discussed Sleepless in Seattle with producer Gary Foster after a 25th anniversary benefit screening at the home of Jack Davies and Kay Kendall in Chilmark. The discussion was moderated by screenwriter and director Scott Frank. Some in the audience still had tears in their eyes when the discussion began, recovering from the final scene of the movie when the two destined lovers finally meet and step into the Empire State Building elevator together, speechless.

“At its core, there’s something magical,” said Mr. Foster of why the film has so much staying power. “There’s destiny, there’s this timeless wish fulfillment that you’re going to meet that person somewhere.”

YMCA director Jill Robie-Axtell thanked the crowd for their support. — Anthony Esposito

Ms. Ryan agreed. “That there’s enough of a benevolent conspiracy happening that your life conspires to meet his life,” she said. “And there’s something so hopeful and universal about that.”

The film’s director and co-writer, the late Nora Ephron, was the subject of much of the conversation. Ms. Ryan remembered visiting the building in New York where Ms. Ephron and Rosie O’Donnell both lived.

“I remember her saying, Rosie, Rosie, a housekeeper problem is still a problem,” Ms. Ryan said.

Mr. Foster recalled Ms. Ephron’s endless Rolodex. He said the iconic final scene at the top of the Empire State Building almost couldn’t be shot on location. He went to Ms. Ephron to tell her the building’s owners wouldn’t allow it, and Ms. Ephron pondered for a moment.

“Nora’s philosophy was you are two phone-calls away from anyone,” Mr. Foster said. She called a friend of hers who was a publicist in New York, specializing in damage control. The publicist happened to represent Leona Helmsley, the owner of the building who was then in jail for tax evasion. While making a visit to her in jail, the publicist appealed to Ms. Helmsley on the film’s behalf.

“She said, okay, they get six hours,” Mr. Foster said.

Six hours is not a lot of time for filming and the crew only managed to get a few shots at the actual building, including the shot from above in a helicopter. Everything else had to be filmed on a separate set, built on a Navy base in Seattle. The Navy initially said no as well, but Ms. Ephron knew someone.

Event took place at home of Jack Davies and Kay Kendall. — Anthony Esposito

She called then senator John Warner, who was also former secretary of the Navy. It all got worked out.

Ms. Ryan may have starred in the movie, but Mr. Foster said he got his moment too. When Tom Hanks’s character, Samuel, goes on his first date after the death of his wife, Mr. Foster, about 30 at the time, can be seen sitting in the restaurant at the table behind him.

“He got mad at me,” he said of Mr. Hanks. “I was too loud.”

In his introduction of the night’s special guests, fundraiser host Mr. Davies took a moment to thank Ms. Ryan for her work on another popular Nora Ephron film, You’ve Got Mail. Mr. Davies is a former AOL executive.

“That helped our stock price a lot. We have you to thank for all of this,” he joked, gesturing at the sweeping Chilmark property.

The event raised more than $250,000 for the Martha’s Vineyard YMCA, Mr. Davies estimated. He thanked the attendees for their support. YMCA director Jill Robie-Axtell said the funds would go toward serving the Island community from childcare to senior services. She said they hope to build a gymnasium and are fundraising for that effort as well.

“We’re very very thankful to all of you for continuing to support us,” she said. “We could not sustain it without you.”