Skip to content
  • Essence GU
  • Beautycon
  • NaturallyCurly
  • Afropunk
  • Essence Studios
  • Soko Mrkt
  • Ese Funds
  • Refinery29
  • WeLoveUs.shop
  • 2026 ESSENCE Festival Of Culture
  • Celebrity
  • Fashion
  • Beauty
  • Lifestyle
  • Entrepreneurship
  • News
  • Shopping
  • Video
  • Events
  • Subscribe
Home • Relationships

Workplace Romances: The Good, Bad & Ugly

workplace romances
By Essence · Updated October 29, 2020
Getting your Trinity Audio player ready…
01
Mixing Business and Pleasure

In these tough financial times, with people working longer hours, office romances are on the rise. We explore famous couples who have mixed business and pleasure, from the President and First Lady to the biggest stars in Black Hollywood.

Workplace Romances: The Good, Bad & Ugly
Corbis
02
Love of My Life

Erykah Badu will forever be known as the woman who got rapper turned actor Common to wear crochet pants. Ms. Badu denies that her allure is that powerful but the musical pair did share a courtship that bloomed in front of our eyes between 2000 and 2003. Both creative Pisces, these former lovers were introduced through a mutual friend after Common expressed he wanted to work with Badu after hearing her first single, “On and On.” The duo won a Grammy in 2003 for their collaborative single, “Love of My Life.”

Workplace Romances: The Good, Bad & Ugly
Getty Image
03
Two for One

Queen of Hip-Hop Soul Mary J. Blige gets a two-for-one combo with her husband of nearly six years, Kendu Isaacs; he is also her manager. Though working with a love interest is never easy, Blige seems happier than ever in her relationship with Isaacs. In addition to making hits, the pair co-parent Isaac’s three children from a previous relationship.

Workplace Romances: The Good, Bad & Ugly
Getty Image
04
Soon As I Get Home From Work

Former power couple Babyface and Tracy Edmonds were married for 13 years before splitting in 2005. “Face” and Edmonds worked together constantly on various projects and even produced movies and TV shows together, including the classic flick “Soul Food.” They are parents to Brandon and Dylan, and Babyface just welcomed a daughter with girlfriend Nicole Pantenburg last fall.

Workplace Romances: The Good, Bad & Ugly
Getty Image
05
Fashion Fusion

Kimora Lee and Russell Simmons met in 1992 during New York Fashion Week. She was 17 and about to finish high school; he was 35 and a self-admitted ladies man. Friends like Tyra warned Kimora not to get involved with the hip-hop mogul but eventually the two started dating and later wed in 1998. They have two daughters—Ming Lee, 9, and Aoki Lee, 6—but officially divorced in January 2009.

Their careers continue to collide while they collaborate on Phat Farm and Baby Phat projects.

Workplace Romances: The Good, Bad & Ugly
Getty Image
06
Bonnie and Clyde

A sincere passion for music brought southern belle Beyoncé and Brooklyn b-boy Jay-Z together. When the hardworking pair released Jay-Z’s hit single “’03 Bonnie and Clyde” in 2002, rumors quickly began to swarm about the pair being more than just friends. They remained tight-lipped about their relationship and continued to be hush-hush even after their secret wedding in April 2008. Only recently have we seen a lil’ PDA from hip-hop’s king and queen.

Workplace Romances: The Good, Bad & Ugly
Getty Image
07
Age Ain’t Nothing But a Number

He was a young platinum-selling R&B star and she was an older fashion stylist/budding designer and single mother. They were an unlikely couple to many but after years of working together professionally, the two took things to the next level and jumped the broom in 2007. They’re now the proud parents of Usher Raymond V, 1, and Naviyd Ely, 5 months.

Workplace Romances: The Good, Bad & Ugly
Mike Colon Photographers/© Tameka and Usher Raymond/Getty Images
08
The Mogul and the Model

Sean “P.Diddy” Combs was a rookie NYC A&R when he met Georgia peach receptionist and aspiring model Kim Porter at Uptown Records in the 1990’s. The duo shared a sometimes public on-then-off-again relationship but seem to be officially split (for now). They continue to co-parent their pre-teen son Christian and toddler twin daughters D’Lila Star and Jessie James.

Workplace Romances: The Good, Bad & Ugly
Getty Image
09
There’s a Thin Line. . .

Surely the relationship between pop princess Rihanna and R&B crooner Chris Brown indicates that mixing work and pleasure doesn’t always end well. Rumors of the pair being more than just friends began to swirl when Brown appeared on the remix of Rihanna’s smash hit “Umbrella” in 2007. Brown is currently scheduled to appear in court on June 22 and is charged with assaulting Rihanna back in February.

Workplace Romances: The Good, Bad & Ugly
Wire Image
10
Double or Nothing

When Sanaa Lathan was cast as Omar Epps’s love interest in “The Wood” in 1999, it didn’t take much acting since the two were already a couple. That real chemistry paid off when they auditioned and were cast as friends turned lovers in “Love and Basketball.” Their breakup a few years later will likely impede our dream of a follow-up to the hit film.

Workplace Romances: The Good, Bad & Ugly
Getty Image
11
Romance vs. Finance

Are you in the midst of an office rendezvous or considering embarking on one? We highly suggest you check with your organization’s human resources policy on such activities first and always keep things professional in the midst of colleagues. In this employment environment, you might regret losing a position (and having to find another one) based on a mere crush or fling.

Workplace Romances: The Good, Bad & Ugly
Getty Image
12
The Idealistic Intern

Before he called the White House home, President Obama was a law student interning at a Chicago firm who couldn’t keep his eyes off of his supervisor for the summer, First Lady Michelle. She was reluctant to take his advances serious, and even after dating they kept things quiet and took the relationship slow. A few years later, the two married and went on to change the world.

Workplace Romances: The Good, Bad & Ugly
Getty Image
13
His Leading Lady

It’s sometimes tough for models to breakthrough in the acting world, so it definitely helps if you are dating one of the hottest directors in town. John Singleton cast his girlfriend Tyra Banks as the lead character Deja in his 1995 film “Higher Learning.” Though the two split, the role remains the most notable in her film career.

Workplace Romances: The Good, Bad & Ugly
Getty Image
14
Art Imitates Life

Halle Berry and Michael Ealy lit up the screen in the 2004 television film “Their Eyes Were Watching God,” based on Zora Neale Hurston’s novel. Their sizzling scenes as Janey and Teacake sparked a real connection and the two continued to date after the cameras stopped rolling. Though they parted ways after a few months of dating, we were happy to see Halle smiling following her divorce from Eric Benet. She showed how to mix business and pleasure with class.

Workplace Romances: The Good, Bad & Ugly
15
Mogul and the Musician

Super-producer Jermaine Dupri and veteran entertainer Janet Jackson shocked many with their romance in 2002, and have been going strong ever since. Though their love is sizzling hot, including Dupri’s new tatoo of his lady, their professional work together with music hasn’t been as successful. Following lackluster sales, together they have joined and left two record labels but their relationship remains platinum.

Workplace Romances: The Good, Bad & Ugly
Getty Image
16
Beauty and the Boss

Ashanti was the reigning queen of Irv Gotti’s label, Murder Inc, since her 2002 self-titled debut, until he recently released her from the label. Rumors swirled speculating the two had intimate encounters and the married producer fueled rumors last summer on Wendy Williams’s radio show. Ashanti doesn’t seem bothered by the label news, as she prepares for her Broadway debut as Dorothy in this summer’s revival of “The Wiz.”

Workplace Romances: The Good, Bad & Ugly
Getty Image
17
The Newlyweds

Talib Kweli just married his girlfriend and collaborator DJ EQ. Their busy schedules and crazy hours in entertainment make their relationship seem ideal, as they hold on to someone who understands the lifestyle.

Workplace Romances: The Good, Bad & Ugly
Getty Image
18
The Balancing Act

Sole and Ginuwine met as fellow artists in the entertainment industry. The two quickly realized they had something special, married and welcomed their first daughter after dating. The family now includes their five children, including two daughters together. Sole removed herself from the entertainment industry to better focus on her family, while Ginuwine continues to record and perform.

Workplace Romances: The Good, Bad & Ugly
19
The Prototypes

Will and Jada Pinkett Smith met when she auditioned to play his girlfriend Lisa on “The Fresh Prince of Bel-Air.” She wasn’t cast but she got the role in real life. Though the two actors work together behind the camera with their production company, charter school and foundation, they have limited their paths crossing on-screen.

“It’s about both of us doing what we love to do, and then doing everything we can for our kids. We just have to do it—together,” Jada said to Will, during an interview with ESSENCE.

Workplace Romances: The Good, Bad & Ugly
Getty Image
20
Behind Closed Doors

The online community WorldWIT found that 61 percent of professional women have dated with a coworker. Commentator and author Michael Eric Dyson weighs in.

“I believe business and pleasure need to be kept separate. Here’s why: Mixing the two can compromise your ability to make good decisions,” he told ESSENCE. “Are you ultimately more obligated to your lover or the company?”

Can office romances work? Share your thoughts below.

Workplace Romances: The Good, Bad & Ugly
Corbis