Did Michelle Pfeiffer date Jack Nicholson? Relationship history explored 

Michelle Pfeiffer encountered most of her significant partners while navigating her high wattage career. While a February 19, 2023, report from Distractify put forward that enduring rumors about a relationship with Jack Nicholson did not hold up to scrutiny, the actress’s known personal timeline remained stacked with other A-list names she met on set.

Michelle Pfeiffer's first marriage to Peter Horton began in 1981. Horton, an actor and director, notably helmed Pfeiffer in the 1985 special One Too Many; she played the love interest of an alcoholic student, played by Val Kilmer. Pfeiffer and Kilmer had a short romantic involvement during this time, despite her marriage. An additional indiscretion followed in 1987: a one-month affair with Alec Baldwin after they starred together in the film Married to the Mob.

The marriage to Horton ended in 1988, catalyzed by Michelle Pfeiffer's affair with her Dangerous Liaisons co-star, John Malkovich. Following the separation, Pfeiffer was linked to Michael Keaton for a year, then spent three years with Fisher Stevens. She finally settled her personal life after meeting television writer and producer David Kelley in 1993. The John Malkovich chapter returned to the news recently, as the actor broke his silence to offer a specific public reflection on their affair.

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John Malkovich on Michelle Pfeiffer affair: Why he regretted losing a ‘great colleague’

During an appearance on the Fashion Neurosis podcast, John Malkovich offered a rare, melancholic reflection on his 1988 liaison with Michelle Pfeiffer, his Dangerous Liaisons costar. When host Bella Freud asked about his “love affair with perhaps the most beautiful woman in the world at the time,” Malkovich responded deliberately. “It's not something I ever really talk about,” the veteran actor began, first explaining the nature of his professional life. He elaborated that making emotional bonds quickly was “kind of part of the work,” but that

“Very rarely, those bonds extend beyond the work.”

Malkovich called Pfeiffer “someone I valued greatly as a colleague,” describing his scene partner as “great fun” and “incredibly fair.” He followed this high praise with a pointed admission of personal fault. By contrast, he added,

“I probably wasn't [fair] — I mean, I certainly wasn't.”

The actor concluded the segment with a profound observation about the cost of the affair:

“I think I've learned over the course of my life that a great colleague is actually kind of rarer than anything, when that relationship becomes more than collegial, or more than a friendship, even a profound friendship, then... you lose a great colleague,” he shared.

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The delayed connection: Why David E. Kelley sat across from Michelle Pfeiffer’s sister

The genesis of Michelle Pfeiffer’s decades-long marriage to writer David E. Kelley, she told Drew Barrymore in 2023, was less fairytale and more logistical nightmare. During her appearance on The Drew Barrymore Show, the actress detailed the profoundly awkward blind date that saw her try to shuffle her future husband onto her own sister. Pfeiffer, feeling “anxious” about the setup, decided to intervene. The intended one-on-one, she recalled, she unilaterally turned into a group event.

“I decided it should be a group date. I still don't know why it was a bad idea,” Pfeiffer said.

She later admitted, when asked if she wanted Kelley for her sister,

“I did — well, only because he wasn’t speaking to me [on the date]. And somehow, I did a bad thing.”

The seating arrangement only worsened the situation in the crowded restaurant.

“We were in this restaurant and there were eight of us, and somehow [David] ended up sitting across from my sister and I ended up sitting across from his best friend,” Pfeiffer explained.

Total silence marked the night between the intended couple.

“We didn’t speak the whole night, and then he left early to go to another party and I thought, ‘Okay that went well,' " Pfeiffer recounted.

The writer finally called two days later, a delay Pfeiffer also deemed “not okay.” Yet, the ensuing hour-long phone conversation “just went [from] that,” successfully salvaging the disastrous introduction.

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Inside the Star-Studded Cast Joining Michelle Pfeiffer in Prime Video’s Latest Seasonal Feature:

Prime Video formally announced the immediate arrival of its anticipated Christmas feature, Oh What Fun, setting the Michael Showalter-directed comedy for a December 3 debut. A trailer drop accompanied the news, cementing Michelle Pfeiffer’s starring role as the titular family’s matriarch, Claire Clauster.

The plot hinges on a profound familial oversight. Clauster’s relatives simply left her alone as they went on a holiday trip, forcing the perpetually devoted host to embark on a spontaneous solo journey. The family’s subsequent panic formed the core of the film.

"As her family scrambles to find her, Claire discovers the unexpected magic of a Christmas gone off-script,” read the official description.

The film featured a sprawling roster of talent surrounding Pfeiffer. That large ensemble cast included Felicity Jones, Chloë Grace Moretz, Denis Leary, Dominic Sessa, Devery Jacobs, Danielle Brooks, Havana Rose Liu, Jason Schwartzman, Maude Apatow, Joan Chen, and Eva Longoria.