Shari Headley's Dating Life Includes Marriage to a Rapper and a Romance with a Writer

Shari Headley's known dating history hasn't gone beyond the 90s. The longtime actress was once head over heels when she met the man who would become her husband. Before she married, she had dated a well-known music manager.

Shari Headley's dating history is short but relatively well-documented. In the 80s, she was romantically involved with entertainment entrepreneur Russell Simmons, who described her as an ambitious woman who wasn't easily swayed by his affection.

In the 90s, Shari Headley met Christopher Martin, a.k.a. Play of the hip-hop duo Kid N' Play. The pair wed and had a child; however, their marriage didn't last long, and her then-husband became estranged from their son. The artist later faced charges of neglecting to pay child support.

The Early Days of Shari Headley and Christopher Martin's Romance

Martin began his career in hip-hop and eventually transitioned into film and TV. His first film role was in the 1990 comedy "House Party," opposite Martin Lawrence and Tisha Campbell. He also starred in the 1991 and 1994 sequels. In addition to acting, he is a producer and composer.

Martin first met Headley at a party in 1991. Their relationship only began the following year when they bumped into each other again at the Black Expo in New York. They announced their engagement in February 1993 and shared some insight into their romance.

Headley said she "knew it was love" when she found a new reason to love Martin as each day passed. The actress added she would never forget the night her then-husband-to-be proposed, as she recalled:

"We were on our way out to dinner when he suddenly asked me to stop the car and pull over. When we got out, he pulled out an engagement ring and said, 'I would be honored if you would become Mrs. Martin.'"

Shari Headley and Christopher Martin's Short Marriage

Headley and Martin tied the knot later in 1993 and welcomed their son, Christopher Martin Jr. It's unclear what led to their separation, but they divorced in 1995, after which Martin became estranged from his son, Headley said.

In August 2001, she accused Martin of failing to pay over $32,000 in child support since their divorce was finalized. Martin would've faced up to five years in prison if convicted; however, how the former couple settled the matter is unknown.

Shari Headley and Russell Simmons's Relationship

In his 2001 memoir, "Life and Def: Sex, Drugs, Money, and God," Simmons revealed that he dated Headley in the 1980s. The pair had met on the set of 1985's "Krush Groove." Simmons was smitten with Headley's beauty but quickly realized she wasn't easy to woo.

He saw Headley as more focused on getting ahead in her career and "didn't see much future in a hip-hop manager." He also felt her mother "hated" him because she thought her daughter could find someone better.

Despite this rejection, Simmons still tried to make Headley happy. He said she was the first woman he bought a "real gift" for — an $800 diamond bracelet. However, Headley wasn't entirely moved by this gesture. Simmons, who has a nephew named after him, recalled that all she said was an unenthusiastic "Thanks."