Business And Pleasure: Celebs Who’ve Dated Their Employees

- By Bossip Staff
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Celebs Who’ve Dated Their Employees

Mixing business and pleasure usually doesn’t end well, but that didn’t stop these celebs from giving it a go.

From maids to managers, hit the flip to see which celebs have dated their employees.


Ariana Grande

After her breakup with Big Sean, Ariana quickly rebounded with her back-up dancer Ricky Alvarez whom she was recently seen slobbing down in public.

Kelley Rowland

Kelly married her manager Tim Weatherspoon last year and had a super adorable son named Titan.


Wendy Williams

Wendy Williams married her husband Kevin Hunter, over 10 years ago.  He also doubles as her manager and they’ve even launched a production company called Wendy Williams Productions.  They seem to be holding on strong despite his confirmed history of cheating.

Nicki Minaj

Before the super-couple Omeeka came about, Nicki Minaj dated her assistant and long time boyfriend Safaree.

Heidi Klum

Long time model and host began dating her security guard Martin Kirsten before even completing her divorce from ex-hubby, Seal. Looks like his replacement was closer than he thought.


Usher has a track record of dating his employees.  He was rumored to have dated a background dancer during his ‘Yeah’ days, then some years back he married his stylist Tameka Raymond.  Their marriage didn’t last long and before he was on to the next coworker.  After one failed marriage with Tameka, Usher decided to try again this January when he popped the question to his manager and girlfriend Grace Miguel.

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    Madonna has a history of dating younger men some of which also happen to be her employees too. Convenient right?  First was her back-up dancer boo Brahim Zaibat who worked for Madonna and her daughter Lordes.  Surprisingly, that lasted a few years before she moved on to her most recent boyfriend Timor who also dances back up for the Queen of Pop.


    For the majority of his career we’ve viewed Fabolous as a single guy until his baby momma revealed on Love & Hip Hop NY that she was the leading lady in his life.  Fab claimed his long time girlfriend Emily B as merely his stylist until she decided she decided to take it public. The pair now have two children after shacking up for over a decade.

    Arnold Schwarzenegger

    Yep, the former Governor of California has also been known to get busy with his employees. In fact, the ex-actor turned politician got caught having an affair with his housekeeper Mildred Baena.  The ties weren’t cut their though, he also fathereda  17-year old son with his former maid.


    What is it about dancers that celeb bangers just can’t seem to resist?  Before her marriage and divorce to Marc Anthony, J-Lo dated one of her dancer Casper Smart.  The pair split ways but recently J-Lo admitted that the two are dating again.

    Mary J. Blige

    Mary’s manager turned husband holds the key to both her heart and business. This year will make their 12 year anniversary. Congrats to them for going strong.

    David Beckham

    When David Beckham was playing for Madrid, his former assistant came out and admitted to having an affair with the athlete.  The allegations were never confirmed by David and shortly thereafter he escaped the drama by moving his family back to the states.



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