Meg Ryan ‘Finally’ Reunites with When Harry Met Sally Costar Billy Crystal — and Teases Something ‘Iconic’ Coming

The pair shared a mysterious reunion photo on Instagram

'When Harry Met Sally' Reunion TCM Opening Night, Arrivals, TCL Chinese Theatre, Los Angeles, USA - 11 Apr 2019 Meg Ryan and Billy Crystal; American actors Meg Ryan and Billy Crystal pose for a portrait in Los Angeles, California, circa 1989. Ryan and Crystal starred in the 1989 comedy/drama film "When Harry Met Sally".

Meg Ryan and Billy Crystal in 2019 (left); Meg Ryan and Billy Crystal in 1989’s ‘When Harry Met Sally’ (right). Photo: Michael Buckner/Variety/Penske Media via Getty; Bonnie Schiffman/Getty

Meg Ryan and Billy Crystal are definitely up to something.

On Wednesday, Jan. 22, the duo shared a photo of themselves on Instagram. The photo was a clear homage to their 1989 film When Harry Met Sally: Crystal, 76, wears a sweater like Harry’s iconic one in the movie and the set resembles the one used for the interviews in the rom-com. The shirt and blazer worn by Ryan, 63, is also reminiscent of Sally’s movie looks.

Ryan wrote in the caption, “It’s finally happening, we’re reuniting for something iconic. Can’t wait to show you all soon 💙.” Crystal also posted the photo and caption to his page — his very first Instagram ever. Fans in the comments were thrilled to see them together, with many wondering what the surprise is.

Ryan and Crystal have been lighting up hearts since they starred in When Harry Met Sally, directed by Rob Reiner and written by the late Nora Ephron. The movie also starred the late Carrie Fisher as Sally’s best friend Marie and the late Bruno Kirby as Harry’s best friend Jess. Both Crystal and Ryan received Golden Globe nominations for the movie, and Ephron’s screenplay was nominated for an Oscar.

Though Ryan worked with Ephron on two more romantic comedies — Sleepless in Seattle and You’ve Got Mail — she and Crystal never appeared in a movie together again. Reflecting on their bond, he told PEOPLE in 2023, “We were thrown together by [director Reiner and Ephron], chosen to be this couple and you never know — almost 35 years later, we’re still a couple to everybody,”

Meg Ryan and Billy Crystal pose for the movie "When Harry Met Sally" circa 1989

Meg Ryan (left) and Billy Crystal in ‘When Harry Met Sally’ in 1989.Hulton Archive/Getty

“As you get further along and new generations see this movie and feel it and watch it over and over again on Valentine’s Day, on New Year’s Eve, whatever it is,” Crystal explained. “You know, people fall in love every day, and people fall out of love every day. This movie is an evergreen that way. It’s a beautiful thing.”

In 2024, the Monsters Inc. star praised his and Ryan’s “fantastic chemistry.” “You knew it was special,” he said of working on the film. “You don’t know that it’s 35 years special.”

For When Harry Met Sally’s 30th anniversary in 2019, Ryan and Crystal got together with Reiner at Turner Classic Movies Festival to celebrate the film. Reiner said of the movie’s appeal at the event, “I think that there are some basic truths about men and women that people connect with, and those kind of things, that dance, that weird dance that men and women do with one another kind of is basic and kind of there all of the time.”