40 Celebrity Couples You Forgot Dated In The Early ’00s

Janet Jackson and Matthew McConaughey

Patricia Schlein/WENN.com
Drew Altizer/WENN.com

I guess Matthew McConaughey was a gentleman because Miss. Jackson was definitely a fan in 2002. That’s right, Janet Jackson and Matthew briefly dated after meeting at the 2002 Grammy Awards, where Matthew thought it was appropriate to wear flannel. The pair didn’t *date* date, but Matthew was seen leaving her Bel Air mansion one morning shirtless and carrying his shoes while whistling. A bit specific with the details there, but legends of an interview where Janet admits the couple swapped more than ideas have swirled for a decade. Matthew and Janet seem to have left it on good terms, with some very friendly red carpet conversations in 2006.

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