It was first performed by the playwright himself with Holland Taylor at the New York Public Library,[2] then opened in 1988 at the Long Wharf Theatre in New Haven, Connecticut, with Joanna Gleason and John Rubinstein.

Other performers paired in the Broadway production included Lynn Redgrave and John Clark, Stockard Channing and John Rubinstein, Jane Curtin and Edward Herrmann, Kate Nelligan and David Dukes, Polly Bergen and Robert Vaughn, Timothy Hutton and Elizabeth McGovern, Swoosie Kurtz and Richard Thomas, Elaine Stritch and Cliff Robertson, Nancy Marchand and Fritz Weaver, and Robert Foxworth and Elizabeth Montgomery.

[5] In 2023, Irish Repertory Theatre, an Off Broadway company in Chelsea revived the play with a rotating cast including Talia Balsam, Laura Benanti, Matthew Broderick, Victor Garber, Brooke Shields, John Slattery and J.

On July 17, 1993, Carol Burnett, Brian Dennehy, Mel Gibson, and Sissy Spacek performed the play at the Sheridan Opera House in Telluride, Colorado.

They included Carol Burnett and Charlton Heston, Brooke Shields and her Endless Love co-star Martin Hewitt, Karen Grassle and Michael Gross, and real-life husband and wife team Jean Smart and Richard Gilliland.

In early 1995, Lynn Redgrave and John Clark, at the invitation of Judge Lance Ito, performed the play for the sequestered jury on their day off, in the same courtroom where the O. J. Simpson trial was being held.

Bernadette Peters and John Dossett performed a one-night-only reading of Love Letters on September 24, 2007, at New World Stages to benefit Opening Act.

[12] In October 2007, Claire Bloom appeared opposite Peter Bowles in a production at the Théâtre Princesse Grace, Monte Carlo, directed by Marc Sinden, as part of his British Theatre Season, in Monaco.

On July 31, 2010, Primetime Emmy Award-winning husband and wife actors Michael Emerson and Carrie Preston read the play at the Charleston Stage.

From January 19–22, 2012, Tab Hunter and Joyce DeWitt performed the play at Judson Theatre Company in Pinehurst, North Carolina, directed by Daniel Haley.

On June 29, 2013 Katharine Ross and her husband Sam Elliott performed the play as a benefit for the Malibu Playhouse at the Edye Second Space, the Broad Stage, Santa Monica, directed by Diane Namm.

Cast Productions has produced several versions of the show, featuring Lorenzo Lamas and Charlene Tilton, Shirley Jones and husband Marty Ingels, and Patrick Duffy and Linda Gray among others.

[20] In October 2015, Canadian actors Sheila McCarthy and David Ferry appeared in a sold-out run of Love Letters in Hamilton, Ontario, directed by Darren Stewart-Jones.

On June 2, 2018, Dan Lauria and Wendie Malick performed the play at Souhegan High School in Amherst, New Hampshire for a fundraiser for the Front Door Agency, a transitional housing non-profit.

[22] On February 22 and 23, 2019, Rensen Chan and Jo Ngai of Hong Kong's The Nonsensemakers (and a husband and wife duo), performed a Cantonese adaptation of the play at the annual Huayi Chinese Festival of Arts at Singapore's Esplanade – Theatres on the Bay.

In February 2023, married actors Tony Shalhoub and Brooke Adams performed a one-night benefit for Georgia Ensemble Theatre, and in September of 2023, Martin Sheen and Melissa Fitzgerald did a short, multi-day run of the play to support addiction recovery month, and follow up on their 2020 virtual collaboration on the show during COVID lockdown.

[29] On Saturday, June 29, 2024, Charles Gibson and Joan Lunden, former Co-Hosts of ABC television's Good Morning America, performed a one-night benefit for the Cape Cod Theatre Project 30th Anniversary Season.