18 Celebrities Who Dated Someone Who Worked For Them

Celebrities have been known to mix a little business with pleasure from time to time, which means dating, and sometimes even eventually marrying people who work for them. It will come as no surprise that Hollywood relationships tend to be fickle at best. Trust us when we say that there have been weirder relationships in Hollywood than one of boss-employee. Celebrities and their employees –
whether that means personal stylists, managers, bodyguards, backup dancers, etc. – tend to spend a lot of time in close quarters together, and things are bound to get a bit heated.

18. Jennifer Lopez

Jennifer Lopez began dating one of her backup dancers Casper Smart sometime in 2011, but officially started talking about their relationship in 2012. Not to mention, they were constantly seen at award shows and events together, posing for pictures on the red carpet. They may have been on-again, off-again, but Lopez introduced Smart to her kids and family, and they even spent some time with her ex-husband Marc Anthony. Alas, they parted ways in 2016 amicably. It was nice while it lasted!

17. Ethan Hawke

Ethan Hawke and his now-wife Ryan Shawhughes met when she was a nanny to his two kids! What’s even more scandalous is that he was married to actress Uma Thurman for nine years when their relationship ended messily in 2005. Hawke later went on to marry Shawhughes in 2008 and has two kids with her, as well. Although there was speculation about the dissolution of his first marriage (as per usual), Hawke told The Guardian that “my marriage disintegrated due to many pressures, none of which were remotely connected to Ryan.” … We’ll believe it when we hear Uma say it.

16. Heidi Klum

Very shortly after divorcing her husband Seal, supermodel Heidi Klum found a rebound in her longtime bodyguard Martin Kristen. Seal severely criticized Klum for turning to Kristen even before they were legally divorced, going as far to tell TMZ to say, “I didn’t expect any better from [the bodyguard]…but I would’ve thought Heidi would [have] shown a bit more class…before deciding to fornicate with the help, as it were.” His rep later clarified that he didn’t mean to suggest that Heidi cheated during their marriage.

At the time, Klum told Kate Couric on her show Katie that Kristen is “a great man” and that she trusts him with her family and children. The couple later called it quits in 2014.

15. Usher

Usher has been around the block a few times with his employees. He dated and married his longtime personal stylist Tameka Foster in 2007, and together they had two kids. Their divorce was finalized in November 2009, and he later married his manager Grace Miguel in September 2015. It’s pretty obvious he is head-over-heels in love with her. In an interview in 2014 with Billboard, he gushed over Grace, saying, “I have an incredible partner and manager. She has helped me through some of the hardest times in my life and my career.” Awww!

14. Ben Affleck (Allegedly)

EVERYONE and their mother knows about Ben Affleck‘s alleged cheating scandal which may have caused a huge rift in his marriage with Jennifer Garner. When news came out that he apparently had an affair with his nanny Christine Ouzounian (typical, if you ask us), it didn’t help matters that many sources claimed things were pretty hot and heavy between the two of them when Jen was away filming. Technically, this is all still speculation, but it still doesn’t make us feel better about Ben and Jen’s strained relationship. While they split around the same time these rumors emerged, they seem to do a great job co-parenting for their kiddos.

13. Britney Spears

Britney Spears most publicized relationship with an employee was obviously her marriage to backup dancer Kevin Federline, but she was also in a serious relationship with her former manager Jason Trawick from 2009 to 2013. They got engaged about two years after dating, but eventually called it quits, with Spears saying in a statement: “I’ll always adore him and we will remain great friends.” “Great friends” sounds like a stretch for a man you’d been engaged to for more than a year, but whatever floats their boat!

12. Christina Aguilera

Although much isn’t known about this pairing, Christina Aguilera was in a pretty serious relationship with her backup dancer Jorge Santos back during the “Dirrty” days. They traveled together on tour and worked on music videos throughout their entire romance, which ended in September 2001. Apparently, she wanted to get married and he felt he was too young at the time. Keep in mind, she was only 20 years old at the time! They still continued to work together afterward, and shortly after, Aguilera met her first husband Jordan Bratman.

11. Madonna

Madonna dated her fitness trainer Carlos Leon back in the 1990s when they met in New York City. In fact, they didn’t just date – he’s the father of her daughter Lourdes. Their passionate affair was brief and Madonna has most definitely moved on since that relationship. Not only did she marry Guy Ritchie, but she also got together with another employee – backup dancer Timor Steffens in 2014. They didn’t last too long but it’s since become pretty apparent that Madonna’s got a penchant for younger men.

10. LeAnn Rimes

Country singer LeAnn Rimes not only married backup dancer Dean Sheremet in 2002, but there have been rumors that she cheated on him with actor Eddie Cibrian, you know, her current husband, while he was married to Brandi Glanville. In an interview after the dissolution of their marriage, Sheremet said that things were already strained between them because of their young age and the professional sacrifices Sheremet felt he had to make to make their relationship work.

9. Rob Lowe

Although there have been dozens and dozens of rumors about Rob Lowe cheating with various nannies, his wife herself worked for him before they got together. Rob and Sheryl Berkoff have been married since 1991, and although they were initially set up on a blind date, it was only when Berkoff started working on the set of Lowe’s movie Bad Influence as his makeup artist that they gave each other a chance and hit it off.
Rob has a lot to attribute to Sheryl, saying in an interview with Haute Living in 2014, “I had met my now wife, Sheryl, and was attempting my first try at monogamy—which was not really in my nature at the time—and I wasn’t able to do it. It made me examine how I was living my life. That led me to getting sober, which led me to changing my life—giving me everything I now have.” Cute.

8. Patrick Dempsey

Patrick Dempsey has been married twice, both times to women who worked for him. His first marriage was to his much-older manager and acting coach Rochelle “Rocky” Parker when he was 21 years old and she was 48. Things ended on a rather bitter note for them and Parker went on to accuse Dempsey of abuse, although she later dropped the allegations.
The Grey’s Anatomy star later married makeup artist and stylist Jillian Fink, and while he technically wasn’t her employer, he sure liked to visit her salon A LOT. The couple has three children together, and after calling off their divorce they seem to be working hard to get their relationship back on track!

7. Kelly Rowland

A successful love story! Kelly Rowland started dating Tim Weatherspoon, her manager, in 2011 and the pair got married in Costa Rica in 2014. Rowland gave birth to their son Titan Jewell Weatherspoon later that year. To this day, the couple is as happy as ever!

6. Celine Dion

Celine Dion met her manager Rene Angelil when she was just a teen, but didn’t start dating him until she turned 19 years old. They got married a few years later and were together until Angelil’s death in 2016. Their love story is a unique one, especially in this day and age. Angelil went to great extents to help Dion’s career, and they had even renewed their vows in Vegas back in 2001. In an interview with ET a couple years ago, Dion said, “I’m not surprised that we married each other, because we have the same dreams. We have the same goals. We respect each other.” We’re not crying, you are!

5. Jude Law

Remember when Jude Law and Sienna Miller were a HUGE thing? Well, there’s a reason why they broke up, and it’s because Jude Law had an affair with his children’s nanny Daisy Wright. Wright spilled the tea to the Sunday Mirror, going as far as to say that they were even caught in bed together by Law’s kids. They may not have had a serious relationship, but their fling caused plenty of damage.

4. Kim Kardashian

Surely, we all remember Kim Kardashiangetting it on with her hot Australian bodyguard Shengo Deane in an episode of Keeping Up with the Kardashians‘ spinoff show Kourtney & Kim Take New York?! There was plenty of on-camera cuddling and kissing going on, and the two pretty heavily suggested on the show that they were going to ~go all the way~. Unfortunately for Kim (or fortunately, given her blissful life with Kanye West and her kids now), Shengo had to jet back to Australia early and cut their fling short. It left Kim quite upset, but as we all know, she definitely bounced back!

3. Ariana Grande

Shortly after breaking up with Big Sean, Ariana Grande dated one of her backup dancers Ricky Alvarez for a year before splitting up in 2016 and rebounding with Mac Miller – her current BF. The public first learned about their relationship when they saw a (bizarre) video of Grande licking donuts with him and lamenting how much she “hate[s] America.” They sure loved to show some PDA during their year-long relationship.

2. Lady Gaga

Lady Gaga recently got engaged to her talent agent Christian Carino! The duo started dating back in February 2017 and was even spotted kissing at the Super Bowl, where Gaga had done her epic halftime Show. Carino works for Creative Artists Agency in Los Angeles, CA, and although things have been pretty low-key between the two of them, to say the least, their penchant for PDA is absolutely adorable.

1. Scarlett Johansson

It’s one thing to take your bodyguard on vacation in Italy, but it’s another thing entirely when said bodyguard looks like he’s checking out your bikini-clad body and you shower together. Apparently the bodyguard had been part of Scarlett Johansson‘s team for two years, and while it was confirmed at the time that she was still dating someone ELSE at the time, the steamy photos suggest otherwise. *Wink wink*

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