Celebs Who Fell In Love With Their Bosses

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Workplace romances have been a thing for as long as employment has been a thing, and it is not uncommon to meet people who are or have been in a relationship with a co-worker. Less common are relationships between supervisors and those they supervise, at least in recent years as the world has become more attuned to the inherent power dynamics at play and the rampant sexual harassment that still plagues our culture (a 2019 study found that 38% of women and 14% of men have experienced sexual harassment at work). 

Despite the clear issues with such a scenario, dating one's boss is still a thing that happens quite frequently — although, because of those power dynamics, larger organizations often require these (and other) workplace romances to be reported to human resources.

But the entertainment industry does not really follow the norms of most other industries, and in Hollywood, dating the boss is not nearly as taboo as it is elsewhere. Film actors date their (sometimes taken) directors rather frequently, and we have also seen a fair number of TV stars falling for showrunners, musicians falling for record executives, and even journalists falling for heads of the network. For our list, we focused on boss-underling relationships that were substantial (versus, say, Kristen Stewart's kiss with her married director Rupert Sanders), and avoided celebrities whose relationships predated their work arrangement. That left us with a pretty hearty list of celebrities who fell in love with their bosses, and some of these people are even still together.

With her golden vocals and that trademark whistle register, we have faith that Mariah Carey would have become famous no matter what route she took. It certainly could not have hurt, however, that she dated and then married her boss at Sony Music. Tommy Mottola became President of Sony in 1988 and Chairman and CEO of Sony Music in 1993. He signed Carey to Columbia Records (a label owned by Sony) after hearing her demo tape in 1988. 

By 1991 the pair were an item, and in 1993 they had an over-the-top $500,000 wedding at New York's St. Patrick's Cathedral. Carey was only 23, while Mottola was two decades older, and neither of them have fond memories of the marriage, which ended in 1998 after a separation the previous year.

Carey has on multiple occasions opened up about how Mottola controlled every aspect of her life during that time period, including in her 2020 memoir. "You might want to picture a child bride," she said in a 2019 Cosmopolitan interview. "There was a conscious effort to keep me as this all-American, whatever that means, girl. It was very controlled. There was no freedom for me as a human being. It was almost like being a prisoner." In a "CBS Sunday Morning" interview, Carey said that even going out for a bite to eat with a friend created a fight in the marriage. Mottola — who has been married to singer Thalia since 2000 — has since acknowledged the inappropriateness of his romance with Carey.

Here is another instance of an actor dating their director, as well as another instance of a very large age disparity. We especially like this love story, though, because it turns the gender expectations on their head — and it is also one of the few on our list that has stood the test of time. 

Actor Aaron Taylor-Johnson met his now-wife Sam Taylor-Johnson when he auditioned for the film "Nowhere Boy" in 2008. Sam — who was married at the time — was directing the film and cast Aaron as John Lennon after his audition dazzled her. She got divorced that same year and the couple made their red-carpet debut (and got engaged) in 2009. "We were very professional through the entire film," Sam told Harper's Bazaar in 2019. "But everyone on set knew. And as soon as we finished, he told me he was going to marry me. We had never been on a date, or even kissed."

The chemistry may have been palpable, but on paper, things looked a bit weird. Aaron was still a teenager at the time (he was born in June 1990), while Sam was a divorced mom of two in her 40s. Though Sam's eldest daughter is only eight years younger than her hot hubby, Aaron stepped up to help raise both kids. The couple also have two other daughters, who they welcomed in 2010 and 2012. The Taylor-Johnsons married in 2012 and are still going strong, despite what Aaron has called the "intrusive" attention focused on their age gap.

By now, we have firmly established that straight male directors tend to fall in love with their leading ladies, and vice versa, but that does not mean we are going to stop giving you examples. This is a cool one, though, since Steven Spielberg and Kate Capshaw are still together today, more than three decades and enough children to form a water polo team later. 

Both stars were previously married before they got together, with each of them bringing one child into the world with their former partners (and Capshaw's daughter is actor Jessica Capshaw, who played Dr. Arizona Robbins on "Grey's Anatomy"). Their blended family has become one of those iconic Hollywood clans we can't get enough of, even though most of the kids live private lives.

Spielberg and Capshaw first met when he hired her to appear as Willie Scott opposite Harrison Ford's Indiana Jones in the 1984 film "Indiana Jones and the Temple of Doom," which he directed. This was Capshaw's big break in Hollywood, but she did not start dating her boss until years later. It was after Spielberg divorced actor Amy Irving in 1989 (they married in 1985) that he and Capshaw got together. They moved in together that same year and married two years after that. In addition to their two children from previous relationships, the couple has five other kids — three biological and two adopted. While Capshaw has not appeared on screen since 2002, a multiple of their kids work in the entertainment industry, including actor Sawyer and director/actor Destry.

In a place like Hollywood, where marriages sometimes last not even a year, a couple who lasts a decade is a huge deal. So, for a celebrity couple to last a quarter of a century is something that should be celebrated, and we are here to toast Judd Apatow and Leslie Mann on that achievement. They have become a fantastic duo over the years, but when the couple first began, Apatow was technically in an authoritative role over Mann. Their first-time coming face to face was at Mann's audition for "The Cable Guy," a film that Apatow helped produce.

Mann scored the role in "The Cable Guy," and she also deeply impressed Apatow, who has said it was love at first sight for him. He told Elle that he said, "There goes the future Mrs. Apatow," as Mann left the room. "I had a soul connection instantly. I meant it. That's why I remember it," he said. Mann and Apatow began dating in 1996, after she was cast in the film, and they got married the following year. They now have two daughters — "Euphoria" star Maude and Iris — and have become one of our favorite funny couples. They have also collaborated again many times, with Apatow casting Mann in films such as "Knocked Up," "Drillbit Taylor," "This Is 40," and "Funny People." The couple most recently collaborated on "The Bubble," a comedy in which their daughter Iris was also featured.

Dame Helen Mirren is an acting icon who can do absolutely no wrong in our book. The legend shines in everything she does, whether it is appearing as no-nonsense Detective Chief Inspector Jane Tennison in the "Prime Suspect" series or hilariously serving as the unexpected narrator for the "Barbie" movie. We trust Mirren's creative choices and, given her long and seemingly happy marriage, also trust her personal ones. Mirren has been in a relationship with director Taylor Hackford since 1986 and married to him since 1997. Hackford was Mirren's boss when they met, but the more shocking part is that Mirren really did not like Hackford at first.

The pair met in 1985, when Mirren appeared in "White Nights," a film that Hackford directed. Mirren initially disliked Hackford because he kept her waiting to audition and she was furious. Once they were on set, however, things quickly developed into romance. The dual Oscar winners dated for over a decade before walking down the aisle, although the wedding was more of a formality than anything. "We got married in the end because we realized that we were going to be together forever," Mirren told AARP. "We got married, ultimately, for legal reasons more than anything else. Estate planning and other complicated things like that." When they wed, Mirren — who told AARP magazine that one reason she fell in love with Hackford was because he was a doting father — became stepmother to Hackford's two adult sons, one of whom died in 2022.

Frances McDormand has been acting for over four decades and has established herself as one of the leading actors of her generation. She has been on fire in recent years — winning Oscars in 2017 and 2020 for her work in "Three Billboards Outside Ebbing, Missouri" and "Nomadland" — and is one of only six actors to have three or more acting Academy Awards (her first Oscar was for "Fargo"). Typically, stars with that level of acclaim have a strong media presence, but McDormand is very much not like her peers in that regard. The actor does not court attention, doesn't do press junkets, and for years following "Fargo" would not give interviews. Heck, she won't even pose for selfies with fans (per The Guardian).

While she is unconventional and sometimes even lovably rebellious, there is one way that McDormand has aligned with the Hollywood norm: falling in love with her boss. McDormand met her husband Joel Coen on her first movie, "Blood Simple," which was also his first film. She auditioned in 1983, and by the time the film came out in late 1984, they were already married. ""It was a revelation that I could have a lover who I could also work with and I wasn't intimidated by the person," she told The New York Times. Coen and his brother Ethan, who are often referred to as the "Coen Brothers," have since cast McDormand in many of their films, including the aforementioned "Fargo," as well as "Raising Arizona," "Burn After Reading," and more.

Forget dating a showrunner or director, why not go all of the way to the top and snag the head of a major network? That is what "Big Brother" host Julie Chen Moonves did when she started up with her husband Les Moonves, who was at the time the head of CBS. Chen Moonves had established herself as a journalist at the network and was a newsreader on "The Early Show" when she was tapped to host "Big Brother." Their romance began while Moonves was still married to his first wife, with whom he has three kids, and details about its origins are scarce. Moonves and Chen Moonves were married in 2004, mere weeks after Moonves's divorce, and had a child, Charlie, in 2009. It is hard to know whether Chen Moonves's career would have been better or worse off had she not married the man in charge.

Chen Moonves only later started using her married name — something she unexpectedly did after allegations of sexual harassment against her husband years after their marriage. "When I married my husband, I chose not to take the name because I thought it could be seen as an unfair advantage," she told Deadline in 2022. "It was a powerful, popular name to have. And I had made my own career prior to knowing him. So, I wanted to keep that." Moonves stepped down from his role at CBS in 2018 amidst the allegations of sexual harassment and misconduct, which he has denied.

Ingrid Bergman and Roberto Rossellini had three children, and one of them went on to find stardom in her own right. A nepo baby before the world knew what that term meant, Isabella Rossellini first found fame as a model, most notably for Lancôme, with whom she signed an exclusive deal in 1982 that made here the best paid model of the time. She also acted, and many people consider the 1986 film "Blue Velvet" to be the vehicle that first properly exposed her skill in that area. And not only did this film help Rossellini's career, but it also introduced her to one of her great loves, David Lynch. By the time of "Blue Velvet," Rossellini had already been married two times — once to director Martin Scorsese and once to Jonathan Wiedemann.

When she divorced Scorcese in 1979, after four years of marriage, Rossellini was pregnant with Wiedemann's child — eerily similar to her parents' story. Things ended with Wiedemann around the time Rosselini met and fell for Lynch, who directed "Blue Velvet" and offered her a part in the film after they met at a dinner party (and Helen Mirren had turned it down). Lynch was married to his second wife Mary Fisk at the time, and his romance with Rossellini was the catalyst for their divorce (again, very similar to her parents' origins). She and Lynch broke up after six years, after which Rossellini adopted a son and became engaged to actor Gary Oldman.

Sean Combs — formerly known as Puffy, Puff Daddy, P. Diddy, and Diddy — changed his legal name to include "Love" in 2021, and it is his love life that we are here to discuss. Combs's most enduring relationship was with Kim Porter, a model and actor who died of a lung infection in 2018. Combs and Porter first dated from 1994 to 1999, but they got back together in 2003 before once again calling it quits six years later. Combs adopted Porter's son Quincy, and the couple also share twin daughters D'Lila and Jessie (Combs also has four kids with four other women). It was around the time that Combs and Porter broke up for the second time(ish) that the rapper began dating Cassie, who worked for him in multiple capacities.

Cassie and Combs kept things a secret until 2012 because, according to Billboard, their relationship overlapped with Combs's on-again, off-again romance with Porter. They also probably knew how it would look for a young singer to be dating her boss, a situation that could have overshadowed Cassie's talent had it become public. The pair met when Cassie modeled for Combs's clothing brand, and he then signed her to his record label, Bad Boy Records. After going public in 2012, the couple started to show up on red carpets and the paparazzi caught them everywhere from luxe vacations to sporting events. They broke up in 2015 but started things up again a couple of times before splitting for good in 2018.

We can think of no better way to end our list than with another case of a director-actor love story, since these are so prevalent in Hollywood and are typically quite fascinating. When it comes to Rose McGowan's last few years, focus has been squarely on her activist work and her role in taking down Harvey Weinstein, as it should have been. But long before McGowan became a sexual assault advocate with no f's to give and a tendency to unleash on Twitter, she was a working Hollywood actor with a loyal following of fans. Though she has not acted in a handful of years, McGowan was always a scene stealer, be it in films like "Scream" and "Jawbreaker," or as witch sister Paige Matthews on "Charmed." She especially shone in darker roles, like the one she had in the film "Planet Terror."

"Planet Terror" is a 2002 film in which McGowan plays a go-go dancer who survives a zombie apocalypse and has a machine-gun for a leg. It was released as part of "Grindhouse," a double feature that also included the film "Death Proof," directed by Quentin Tarantino. The "Planet Terror" portion of the "Grindhouse" was written and directed by Robert Rodriguez, who McGowan met when she was cast in the film. Rodriguez only split from his wife in April 2006, and there were rumors in the media that McGowan was the reason for the marriage's demise. McGowan and Rodriguez were together from 2006 to 2009, and they were even engaged before things went downhill.