When Ms. Jackson and Jermaine emerged arm in arm on red carpets back in the early 2000s fans were more than a little surprised, but nevertheless they rooted for the love they shared. They called it quits in 2009, and Ms. Jackson moved on and married Wissam Al Mana in 2012. The pair are expecting their first child together very soon.
Janet Jackson and Jermaine Dupri
The announcement that Mariah Carey and Nick Cannon were in fact a couple and newlyweds caught most fans completely off guard, but in the end, we were totally here for the once adorable couple and especially for "dem babies", which they call their twin son and daughter Morrocan and Monroe. Nick and Mariah divorced in 2015.!
Mariah Carey and Nick Cannon
It's not every day you think of Grammy winning Toni Braxton and YMCMB's Birdman being romantically linked, but if they like it, we love it! The relationship is still fairly new, so fans are waiting to see if it truly blossoms.
Toni Braxton and Birdman
We're still not sure how this couple came to be, but the union didn't last long enough for anyone to worry much about it. These days they're more like social media enemies than exes.
Vivica A. Fox and 50 Cent
Oprah and Roger Ebert went on not one, but two, dates back in the late 80s. it didn't lasted long either. While the two didn't click romantically, they remained friends until his death in 2013.
Oprah and Roger Ebert
The 90s dating scene wouldn't be complete without a totally scene-stealing couple. Thankfully, supermodel extraordinaire Tyra Banks and singer Seal made that happen for us. Their relationship caught us completely off guard, but we admit, at the time, we were here for it!
Tyra Banks and Seal
No one saw the 90s relationship between Robin Givens and Brad Pitt coming, but even with it's surprising nature, it definitely kept onlookers' attention.
Robin Givens and Brad Pitt
Yes, this happened. Oh Whoopi and Ted, you two were a love affair that we definitely didn't know was on the horizon in the 90s. Who could ever forget that 1993 Friars Club roast?
Whoopi Goldberg and Ted Danson