Matthew McConaughey & Janet Jackson – 2002
One celebrity pairing you would never expect to happen is Matthew McConaughey and Janet Jackson. Sources say they ended up liking each other after meeting at the 2002 Grammy Awards. The two decided to go on a date, but it looks like the date didn’t go so well.
They never called each other back for a second date and moved on with their lives. Jackson hasn’t been lucky with her love life because all three marriages she had didn’t work out. McConaughey was more fortunate, for he has been married to Camila Alves since 2012. He published a memoir called Greenlights in 2020.
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