A 1990s crush, a gentle rejection, and a friendship that lasted
Winona Ryder says she once threw herself at Al Pacino — and he turned her down with grace. In a new Elle UK interview, the 53-year-old actor looked back on the mid-90s, when she was 22 and working with Pacino on his 1996 directorial debut, Looking for Richard. What started as long coffee crawls around New York ended with a candid confession from her and a kind, unmistakable no from him.
Ryder describes Pacino as “obsessed with coffee,” the sort of co-star who knew the out-of-the-way spots. He would take her to the “weirdest places” across the city to try different blends and brews. Those detours became their rhythm during the Shakespeare project, where Pacino played Richard III and also steered the film — part documentary, part drama — through rehearsals, street interviews, and rehearsal-room debates about what Shakespeare means now.
After one of those caffeine-fueled afternoons, Ryder decided to say what she felt. As he dropped her off, she told Pacino, “I love you, you know. I really am completely in love with you.” His reply was soft but decisive: “Aw, honey, noooo.” She says the moment didn’t break anything between them. If anything, it clarified boundaries and cemented respect. They stayed friends.
Their paths crossed again in 2002 on S1m0ne, Andrew Niccol’s Hollywood satire starring Pacino as a director who manufactures a digital actress. Ryder appeared as a sharp-tongued star within that world, sparring on-screen with Pacino’s character during a story about fame, illusion, and the machine behind it. The collaboration underscored what Ryder says was always true: the crush didn’t derail the work. It never even bruised it.
Ryder also says Pacino has kept up a quirky birthday ritual for years. He’ll send a warm message — often jokingly calling her “my wife” — and sign off with “KR” followed by his age, as in “KR 57.” She doesn’t decode the initials, but the shorthand has stuck, a private tag that shows the decades-long continuity of their friendship.
Work, timing, and how sets shape relationships
Set the scene: mid-1990s. Ryder had already run a remarkable arc by her early 20s — Beetlejuice, Heathers, Edward Scissorhands, Bram Stoker’s Dracula, then Little Women. Pacino, in his 50s, was at a different peak after Heat and a string of stage and film triumphs stretching back to The Godfather and Serpico. Looking for Richard brought them into an intense creative space: Pacino probing Shakespeare’s language and ambition; Ryder navigating that world at 22, soaking it in.
Anyone who has worked on a film knows how quickly that environment compresses time. Days are long. Conversations intensify. The work is intimate by design: argument, rehearsal, shared jokes, odd rituals — like hunting down obscure espresso bars — become the scaffold for a friendship. Ryder’s crush isn’t hard to understand inside that bubble, especially with a mentor-figure co-star who’s both generous and larger than life.
What’s striking is Pacino’s response — not just the “no,” but the way the “no” preserved their rapport. Hollywood history is littered with stories of messy boundaries. This wasn’t one of them. Ryder frames it as respectful, a moment that could have gone sideways but didn’t. It’s part of why she talks about it now: the memory is tender, not complicated.
Looking for Richard itself was a passion project for Pacino. He played the hunchbacked, scheming king while questioning, on camera, how to bridge a 400-year-old text to modern audiences. The film roamed from rehearsal halls to sidewalks and classrooms, making room for actors to test lines and for non-actors to react to them. Ryder, still early in a career full of sharp left turns, became one voice in that chorus — and, off-camera, Pacino’s coffee partner, trailing across a 1990s New York that still had hidden espresso dens and no smartphone maps.
By the time they made S1m0ne, both had moved through several career phases. Ryder toggled between studio pictures and indies. Pacino kept jumping between screen and stage. Their on-screen dynamic in Niccol’s satire played out with a knowing wink about Hollywood’s ego and image-making — a playful counterpoint to their earlier, more scholarly Shakespeare outing.
The birthday sign-offs she mentions — “Hey, my wife, I love you. KR [age]” — read like a time capsule stamped with their running joke. She doesn’t spell out what “KR” stands for, only that it’s always paired with his age. It feels like the kind of small code friends share when they’ve logged enough years and stories to need shorthand.
There’s also the age-gap factor: she was in her early 20s; he was in his 50s. Public conversations about power dynamics in the industry are more pointed today. Ryder doesn’t frame her story through that lens. She tells it as a sweet crush and a clean boundary. Pacino was kind. She moved on. They kept working and talking. The detail that she still sees him, decades later, says just as much as the confession itself.
Actors occasionally reveal long-ago crushes that never surfaced at the time or fizzled into jokes later. Keanu Reeves and Sandra Bullock both admitted to quiet crushes on each other during Speed, years after the fact. Friends star David Schwimmer spoke about mutual feelings with Jennifer Aniston in the show’s early seasons. It’s part of the profession’s odd intimacy: perform closeness, then find a way to keep the real-life version respectful, rare, and sustainable.
Ryder’s story lands there — in the sustainable part. She’s now widely recognized by a new generation for Stranger Things, a run that restored her to the center of pop culture. Pacino remains a fixture on stage and screen, the kind of figure who can drop an affectionate line on a birthday and instantly connect two very different eras of Hollywood.
The coffee tours, the brave “I love you,” the gentle “no,” the yearly “KR” sign-off — it all maps a simple arc: a young actor idolizes an older one, says it out loud, and finds a mentor and friend rather than a romance. The anecdote is small. The subtext isn’t. It’s about how a set becomes a world, and how — if you’re lucky — that world doesn’t collapse when the shoot wraps.
Ryder says they still catch up. No drama. No footnotes. Just two artists who made a Shakespeare film in New York, traded messages across the years, and discovered that the best stories don’t always end the way you think — they just keep going.