Stars who have dated their bosses

In many lines of work dating your boss is a major no-no. However, common rules do not always apply to celebrities. We have often seen famous people dating and even marrying their personal trainers, agents, producers or directors. Here are some of those couples.

Mariah Carey








Colombia Records executive Tommy Mottola kick-started Mariah Carey’s career by signing her up to his label after she handed him an impressive demo tape at a party in 1988. And it turns out, that wasn’t all Mottola was impressed by. During the making of her debut album, the pair became romantically involved, and in 1993, they got married. However, their love wasn’t to last, and in 1997, they separated, forcing Mariah not just to find a new publicist and manager, but also to look for a new label.

Kristen Stewart








Back in 2012, it was revealed that Stewart was having an affair with her married Snow White & the Huntsman director, Rupert Sanders. The actress was in a relationship with her Twilight co-star Robert Pattinson at the time. They eventually split and Sanders got divorced because of the scandal.

Britney Spears








In 2009, Britney’s relationship with her agent Jason Trawick became a little bit more than just professional. Though the pair have since split, prior to their 2012 engagement, they severed their working relationship and Trawick left talent agency William Morris Endeavor in order to pursue a career less close to home.

Aaron Johnson








There’s a long and convoluted history of directors dating their muses, but eyebrows were certainly raised when Sam Taylor-Wood, then 42, struck up a romantic relationship with young lead actor Aaron Johnson (then 19) on her film, Nowhere Boy. The couple, who have since welcomed two children together, also tied the knot in 2012 and famously changed their surnames to Taylor-Johnson.

Casey Wilson








The actress met the love of her life on the set of the recently-cancelled sitcom, Happy Endings. She began dating the show’s creator, David Caspe, at the start of the series, and the twosome announced their engagement this past September. During her interview on The Late Late Show with Craig Ferguson in November 2013, Wilson stated that they set their wedding date for May 2014.

Reese Witherspoon








The Academy Award-winning actress, who has two children with ex-hubby Ryan Phillippe, began dating her talent agent, Jim Toth, in 2010. The two were married in 2011 and welcomed son Tennessee into the world the following year.

Robert Downey Jr.

Robert Downey Jr and Susan Downey







Robert Downey Jr. hooked up with his film producer boss Susan Levin, who at the time was the Executive Vice President of Production at Silver Pictures. In 2005, the pair went all the way and tied the knot, but Susan resigned from her position at Silver Pictures to put some professional distance between her and Downey Jr. In early 2012, the couple welcomed their first child together, too.

Hilary Swank








The two-time Academy Award winner, who famously forgot to thank her then-husband Chad Lowe while accepting her first Oscar, began dating her agent, John Campisi, a few months after she and Lowe announced their split. They were in a relationship for almost six years when they called it quits in 2012.

Milla Jovovich








Supermodel Milla Jovovich started a whirlwind romance with her director, Luc Besson, after she starred in his movie The Fifth Element. The pair married in 1997, but divorced just one year later.


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4 responses to “Stars who have dated their bosses”

  1. Penelope says:

    We are all people and we break the rules. Dating the boss, the director, producer, agent, representatives considered a big no-no from professional point of view, but to love all hearts are submissive, even professionally dependable on each other people. When people fail to resist we get what we get. As you can see most of the couples broke. Well this could be due to the ‘bossy’ reason, but the couples simply do not last among celebrities recently. In their majority these are not long affairs or marriages.

  2. Samantha says:

    I guess it is very easy to fall in love when you are spending a lot of time together with the person, so no wonder that a lot of actors and actresses are getting divorced or split up with their soul mates if they are engaged in a same project for a too long time. Like for example same happened with Brad Pitt and Angelina Jolie, I don’t remember about Angelina whether she was in a relationship at that moment or not, as she was getting separated and back together with Billy Bob Thornton for so many times that I already stopped realizing at some point when they are together and when not. But Brad Pitt certainly was occupied, and not in some simple relationship but marriage. I never thought that Brad and Jennifer would ever divorce they seemed to be such a perfect couple, but now I realize that everything that happens in this life, happens for a reason. At first I didn’t really respected Angelina for stealing a man from its family, but later I realized that who am I to judge them, and the fact that they are together for so many years already and have children together but still love each other truly, madly, deeply is speaking about it.

  3. Lucy says:

    Awe I love the movie “Fifth Element” and the actress Milla Jovovich, she is so much fun, always positive and communicative and smiling. I guess it is very pleasant to hold a conversation with her, for some reason I am perfectly sure that although she is a huge star, she is not really of those people who like to show off and pretend that they are such stars and everyone else around them is not even worth speaking with. But before this article I never knew she was married with Luc Besson, he is also very great, but probably has a too rude character and I am sure he was the reason for their separation; she doesn’t look like a person who can make scandals. Well, I have no idea who will eventually become the person Milla will choose, but I am sure it will be a kind and decent person, hopefully he will not be an actor as well (as being away from each other while filming in different even countries from time to time, is really affecting the relationship and mutual trust).

  4. Sally says:

    Well there certainly are many couples that were built during mutual work under same project, but I am wondering why here are only listed the ones that didn’t last for a too long time, like for example we all know such couples as: Brad Pitt and Angelina Jolie, or Julia Roberts and Danny Moder. Those couples were also created during work under same movie, but those couples have shown their love, loyalty and total devotion towards each other and their families for many years in a row. I think I would enjoy much more to read an article about them. Or for example about Ben Affleck and Jennifer Garner, than those two were getting married some mean people were saying that they will not last for too long, as Ben is kind of still in love with Jennifer Lopez, but those were rumors based on nothing, their love has overcome all those things, and I am really happy for them, I wish those couples would show example to the rest of Hollywood pairs, that besides getting divorced and leaving the family as soon as some hard times come there are some other options, like staying and trying to fix what is broken.