14 Celebrities Who Dated Their Employee

14 Celebrities Who Dated Their Employee


Dating a coworker can be problematic, but hooking up with an employee is even more rife with opportunities to go terribly wrong. However, that hasn't stopped a slew of celebrities from dipping their toe in the underling pool.

From nannies to backup dancers, read on to find out which famous stars have dated someone on their celebrity payroll.


Image via Jose Hernandez/ZUMA Press/Corbis

  • Heidi Klum


    Image via KCS Presse/Splash News

    After her marriage to Seal fell apart in 2012, model and mom of four Heidi Klum found love again with someone who made her feel safe, her bodyguard Martin Kristen. The pair dated for a little over a year before calling it quits in early 2014.

  • Usher


    Image via Lee/Elatab/Winslow/Macpherson/Splash News

    Picking out her husband's clothes must have come naturally for stylist Tameka Foster when she married Usher in 2007. The two met on the set of one of his music videos, and after tying the knot, they had two kids together. Sadly, Usher and Tameka's marriage was short-lived. They divorced in 2009.

  • Jennifer Lopez


    Image via Joe Stevens/Retna Ltd./Corbis

    When Jennifer Lopez first started dating a much-younger backup dancer named Casper Smart in 2011, many people mistakenly assumed that their relationship would be a brief fling! But, despite their 17-year age difference, several breakups, and the fact that J.Lo is Casper's boss, the lovebirds are still together over five years later.

  • Christina Aguilera


    Image via London Entertainment/Splash

    A production assistant is the lowest paid employee on any film set, and a movie's star is often the highest, so imagine people's suprise when Christina Aguilera fell in love with a lowly production assistant named Matt Rutler on the set of her film Burlesque in 2010. The couple became engaged in 2014 and welcomed a daughter named Summer Rain later that year.

    More from The Stir: 14 Celebrity Couples Who Also Work Together

  • Madonna


    Image via TK/Splash News

    After splitting from ex Guy Ritchie in 2008, Madonna, 57, dated a string of handsome, young backup dancers who danced on tour with her. First, there was 25-year-old Brahim Zaibat (pictured here with Madonna at the 2013 Met Gala). Then, following rumors that Brahim cheated with Madonna's trainer, the Material Girl moved on to Timor Steffens, 26. In more recent years, she's been linked to 25-year-old South African model Aboubakar Soumahoro.

  • Ethan Hawke


    Image via Phil Ramey/RameyPix/Corbis

    While still married to Uma Thurman, Ethan Hawke allegedly began an affair with the couple's nanny, Ryan Shawhughes, in 2003. The actor married Ryan in 2008 after his divorce from Uma was finalized, although he denies that infidelity was to blame. "I met Ryan through my literary agent, and she was indeed one of Maya and Levon's nannies during a film shoot. After a short period of working for me, Ryan went back to Columbia to get her degree. There were never any scandalous thoughts or actions back then," he said in a 2009 interview.

  • LeAnn Rimes


    Image via NCNA/RameyPix/Corbis

    Add LeAnn Rimes to the list of singers who've fallen in love with one of backup dancers! The country star was only 20 years old when she married dancer Dean Sheremet. However, their marriage ended in 2010 after LeAnn left him for her now second husband, Eddie Cibrian.

  • Simon Cowell


    Image via Cook/Splash News

    American Idol may have introduced Simon Cowell to an American TV audience, but it also introduced him to his one-time fiancée, Mezhgan Hussainy. The pair met while Mezghan was working as a makeup artist on the show and became in engaged in 2010, around the same time that the on-air judge left the show. Less than a year later, the couple announced their breakup.

    More from The Stir: 20 Celebrity Couples With a Huge Age Difference Between Them

  • Hilary Swank


    Image via GAMEPIKS/RameyPix/Corbis

    Oscar-winning actress Hilary Swank put her career in the hands of her agent, John Campisi, and in late 2006, fresh off a divorce from ex-husband Chad Lowe, she put her heart in his hands as well. After dating for over five years, they ended both their personal and professional relationship in 2012.

  • Rob Lowe


    Image via Stephane Cardinale/People Avenue/Corbis

    Although they first met on a blind date, Rob Lowe didn't begin to seriously date his future wife Sheryl Berkoff until she worked as his makeup artist on the set of the 1990 film Bad Influence. The two married the following year and are still together, 25 years and two sons later.

  • Britney Spears


    Image via Phil Ramey/RameyPix/Corbis

    Pop star Britney Spears is no stranger to dating underlings! After divorcing former backup dancer husband Kevin Federline, Brit rebounded with a string of men, including her agent Jason Trawick, whom she got serious with and even agreed to marry in 2012. Sadly, Britney and Jason called off their engagement the following year.

  • Patrick Dempsey


    Image via Dziekan/Retna Ltd./Corbis

    Jillian Fink must give one heck of a haircut! The makeup artist and hair stylist met TV star husband Patrick Dempsey when he booked an appointment at her salon. The couple married in 1999 and despite briefly separating last year, they are still together. Jillian reportedly still cuts his hair to this day.

    More from The Stir: 20 Celebrity Couples Who Got Engaged or Married on Valentine's Day

  • Jude Law


    Image via Stephane Cardinale/Corbis

    While engaged to Sienna Miller in 2005, Jude Law made tabloid headlines when it was reported that he had cheated with Daisy Wright, his children's nanny. Jude made a public apology to Sienna; however, it wasn't enough to save their relationship, and their engagement was promptly called off.

  • Natalie Portman


    Image via Stephane Cardinale/People Avenue/Corbis

    Not only did the 2010 film Black Swan give Natalie Portman an Oscar, it also scored her a husband! The actress met dancer Benjamin Millepied while he served as the movie's choreographer, and they wed in 2012.

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