A.R. Gurney’s Love Letters is a play about love and connection, regret and missed opportunities, memory and reflection. But mostly it’s about two childhood friends sharing more than 50 years of their lives in letters.

The messages in the play can land differently depending on a listener’s age and experiences. That’s why Oscar nominee and four-time Emmy Award winner Alfre Woodard recently had to set aside the script, too emotional to continue, after just the first two pages. She first performed the play in her 20s, then again in her early 40s after her children were born. Now, at 71, she’ll play Melissa Gardner once more in a Dec. 16 benefit reading at Wellfleet Preservation Hall.

“I picked this up and got all verklempt,” said Woodard. “It’s going to be a whole different ball game reading at a mature age, but I’m game to try it.”

The Wellfleet audience may be discovering the play at the same time Woodard is rediscovering it.

“I put it down because I didn’t want to know where I would be going,” she said. “With a reading, you really want it to just happen.”

Woodard, who was named one of the 21st century’s 25 greatest actors by the New York Times, first read the play onstage with her husband, actor-turned-writer Roderick Spencer, and then in Beverly Hills with friend Blair Underwood. For the Wellfleet event, Woodard asked Jeff Zinn, former artistic director of the Wellfleet Harbor Actors Theater and former managing director at the Gloucester Stage Company, to costar as Andrew Makepeace Ladd III.

“I know your weight as an actor and a human being,” she said to Zinn, 74, when they were together at the hall to map out show details. “When it’s a reading, you’ve really got to be grounded, because there’s nothing else to support that moment of ‘Come in and experience this with us.’ I’m a bit flighty, and I knew you would keep me tethered.”

“I’m just going to get on the bus and ride,” said Zinn, who lives in Orleans. “Not think too much about how it’s going to come off, and be with Alfre, and trust her.”

The letters passed between Melissa and Andrew cover the years 1937 to 1985, relating thoughts on college, ambitions, hopes, politics, marriages, disappointments, children, and aging. Andrew becomes a U.S. senator, Melissa an artist, and their distanced love grows beyond friendship.

Zinn first met Woodard briefly about 20 years ago at a New York City performance based on A People’s History of the United States by Howard Zinn, Jeff’s father. Then last summer Woodard agreed to be interviewed for Zinn’s Gurus: The Story of Acting podcast. Coincidentally, she was also being brought on as part-time artistic director of Preservation Hall by former executive director Kathy Fletcher — her friend from the world of arts and social justice advocacy. Zinn and Woodard later got better acquainted when they went to see Bread & Butter at Wellfleet’s Harbor Stage Company.

Woodard, smitten with visits to the Outer Cape and its arts community, says she’s wanted to help the hall however she could through a term that ends this spring, and Fletcher suggested Love Letters. The holiday timing fits, Woodard says, because of the play’s reflection on the importance of families, or chosen families, as the actual gift and richness of life.

Zinn was intrigued by the script’s universality, considering Gurney’s two characters were originally written as wealthy WASPs. Neither he nor Woodard fits that description.

“But any well-written play can be performed by anyone who works well,” said Woodard. “It can be presented to any audience, no matter the DNA of the people in the story.” She noted that “the Black bourgeoisie” world of her Tulsa, Okla. childhood is rarely depicted on film but has similarities to this play’s background. “The truth about this story is that it touches everybody’s life.”

Many Cape Cod arts groups have used the play, a 1990 Pulitzer Prize finalist for drama, as a fundraiser, often starring prominent community members. The play can be produced for one night or short runs and with a rotating cast, because little preparation is required for two actors to sit facing the audience and read letters. Two desks with chairs are typically the set.

Though the staging may be simple, Woodard and Zinn emphasize that description doesn’t apply to this story of deep connection between two people coming together and moving apart over decades.

“The material is so rich,” Zinn said. “I don’t feel I have to emulate some guy that I’m not. I am that guy. His history is very different from mine, but I can still relate to it. I’ve had that kind of dynamic with people in my life.”

Woodard is drawn to the letters themselves, a form of correspondence unfamiliar to generations used to texting. She talked about a cherished letter from her grandmother, sending postcards to her parents while traveling overseas, and what her two children sent while away at camp. Woodard once created a scrapbook of every note Spencer wrote to her in the first five years of their relationship.

“Letters are intimate,” she said. “Letters are a moment in time that you can revisit, as opposed to memories that change as you grow.” And love letters, no matter what type of love is shared, can be the most precious of all.

Written Word

The event: Benefit reading of A.R. Gurney’s Love Letters
The time: Saturday, Dec. 16, 5 p.m.
The place: Wellfleet Preservation Hall, 335 Main St.
The cost: $75 at wellfleetpreservationhall.org