10 Lesser-Known Celebrity Couples From the 1990s

Who knew these big name stars actually dated?

Courtney Cox and Michael Keaton

10 Lesser-Known Celebrity Couples From the 1990s
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For six years, Friends star Courtney Cox was seriously involved with Batman hunk Michael Keaton. The couple split in 1995, but according to Cox, the two are still on good terms.

Jennifer Love Hewitt and Joey Lawrence

10 Lesser-Known Celebrity Couples From the 1990s
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So, apparently they only lasted for a few months. Even so, this is one beautiful couple made in peak 90s heaven.

The two dated at the height of their popularity, with Jennifer Love Hewitt starring on Party of Five, and Joey Lawrence stealing hearts as a regular on the sitcom Blossom.

Tyra Banks and Seal

10 Lesser-Known Celebrity Couples From the 1990s
NY Daily News

In 1996, supermodel Tyra Banks was involved in a brief, and relatively private relationship with British singer Seal. Banks only stayed with the “Kiss From a Rose” crooner for a few short months. In 2005, he went on to marry Banks’ friend and fellow Victoria’s Secret angel, Heidi Klum.

Tionne “T-Boz” Watkins and “Mr. Dalvin” DeGrate

10 Lesser-Known Celebrity Couples From the 1990s
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By now, most people know of the rollercoaster that became of singer Mary J. Blige and Jodeci front man, K-Ci Hailey’s, relationship. But did you know that TLC’s T-Boz also dated a Jodeci member?

In the mid 90s, T-Boz and Jodeci bad boy Mr. Dalvin were a steady thing. Rumor has it that Dalvin wasn’t the most faithful companion, and even inspired TLC’s 1996 hit “Creep” after he slept with T-Boz’s close friend. Needless to say, this led to the couple’s ultimate demise.

Drew Barrymore and David Arquette

10 Lesser-Known Celebrity Couples From the 1990s
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We all loved Drew Barrymore and David Arquette as the adorable siblings in Never Been Kissed. But in a 2014 interview, Arquette revealed that he and his costar dated when they were younger. The actor described Barrymore, who also made a brief appearance in his 1996 film Scream, as “one of the sweetest, kindest people in Hollywood”.

Jennifer Aniston and Paul Rudd

10 Lesser-Known Celebrity Couples From the 1990s
NY Daily News

Remember when Paul Rudd appeared on Friends as Phoebe’s handsome beau, Mike? Surprisingly before that, Rudd actually dated Jennifer Aniston, whom he met while filming the 1998 movie, Object of My Affection.

Teri Hatcher and Michael Bolton

10 Lesser-Known Celebrity Couples From the 1990s
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Hate him or love him, Michael Bolton was the man throughout the 1990s. With hit songs like “How Am I Supposed To Live Without You”, Bolton was also a hit among the ladies, eventually catching the eye of a young Teri Hatcher when she starred in his 1991 video, “Missing You Now”. A year later, the actress snagged her signature role as Lois Lane in Lois & Clark: The New Adventures Of Superman. Bolton eventually dated and got engaged to Hatcher’s Desperate Housewives costar, Nicollette Sheridan.

Winona Ryder and Matt Damon

10 Lesser-Known Celebrity Couples From the 1990s
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It’s hard to believe these two megastars were able to keep their relationship relatively private. Nonetheless, Winona Ryder and Matt Damon did just that, quietly dating for almost two years before ultimately going their separate ways.

Madonna and Tupac Shakur

10 Lesser-Known Celebrity Couples From the 1990s
People

This summer, a letter written by icon Tupac Shakur revealed that he and Madonna were once involved in an intimate relationship. The memo, penned by the late rapper while he was in prison, suggests that he was the one who ended the brief partnership – voicing a concern that the interracial romance would spark controversy if publicly disclosed.

Tyra Banks and Will Smith

10 Lesser-Known Celebrity Couples From the 1990s
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If you’re a The Fresh Prince of Bel-Air fan, you may recall that Tyra Banks had a reprising  role during the sitcom’s sixth season. Sparks undoubtedly flew whenever her and Will Smith’s character shared the same scene, but the pair’s chemistry apparently continued off the small screen. In fact, the couple dated for a year before Will became exclusive with now wife Jada Pinkett Smith.

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