11. Janet Jackson & Jermaine Dupri
Janet Jackson and Jermaine Dupri were together from 2002 to 2009. It’s kind of hard to find anything about their relationship, as the pair kept kind of private while they were together. Now, Dupri has been quoted in several interviews and in several articles for admitting that he messed things up with Jackson.
In recent interviews, Jackson has also opened up positively about her and Dupri’s past relationship. Over the course of her life, Jackson recalls being made fun of for her body or just not feeling comfortable in her skin. Dupri was one of the only people that made her feel beautiful in her body.
Jackson, 50, is now pregnant with her current husband, whom she married in 2012. Jackson and Dupri are another couple that are just a tad bit apart in the height department. Jackson is 5’5″ while Dupri is 5’4″. While the pair was together, they collaborated on a few music projects as well.
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