By April Littleton

Everyone has heard the saying “opposites attract,” but we still can’t help but wonder how certain celebrities end up with some of the people they date. Is it their personality? Or maybe it’s because of their outlandish style. Whatever the case may be, some of the most average-looking celebrities end up with the most stunning beauties in America. Here’s a list of celebrities Cupid thinks date out of their league:

Jermaine Dupri and Janet Jackson: Everyone was stunned when the producer, rapper and songwriter confirmed to the public that he was dating Janet Jackson. The duo dated for eight years until they finally called it quits in 2009.

Related: 5 Celebrity Couples that Waited for Marriage

Jamie Kennedy and Jennifer Love Hewitt: Kennedy dated his Ghost Whisperer co-star from March 2009 to March 2010. However, the relationship wasn’t smooth sailing when harsh criticisms about their love affair hit the newsstands. In an interview for People, Kennedy said dating Jennifer Love Hewitt wasn’t easy when no one wanted them together in the first place.

Marilyn Manson and Dita Von Teese: This isn’t the first time the musician, actor and painter landed such a hottie. Manson was engaged to Rose McGowan from February 1998 to January 19, 2001 before he met Dita Von Teese on the set of one of his music videos. They became a couple on his 32nd birthday. They married in 2005 only for Von Teese to file for divorce a year later due to irreconcilable differences.  In an interview with the Sunday Telegraph, she said, “I get the impression he thinks I was unsupportive, but the truth is I wasn’t supportive of his lifestyle, and someone else came alone who was.”

Macaulay Culkin and Mila Kunis: The world never understood the relationship between these two celebrities. Culkin began dating the That ‘70s show actress in May 2002. The couple stayed together for nearly 9 years -  longer than anyone would have guessed. On January 3, 2011, Kunis’ publicist confirmed their breakup. The duo remain friends while Kunis has moved on to Ashton Kutcher.

Kris Humphries and Kim Kardashian: Even though the Keeping Up with the Kardashians star is in a happy relationship with Kanye West and is a new mom to baby North, we can’t forget about her brief marriage to Kris Humphries. The basketball player began dating Kardashian in October 2010. They became engaged in May 2011 and married that same year in August. The wedding was highly publicized and even had its on two-part TV special. However, the marriage didn’t end in bliss. Just 72 days later, Kardashian filed for divorce.

Related: Celebrity Couples Who Met on Set 

Russell Brand and Katy Perry: To this day, we still don’t know what the Teenage Dream singer saw in Russell Brand.  The couple began dating after meeting for the second time at the 2009 MTV VMAs. The pair became engaged in December of that year and married in a traditional Hindu ceremony in October 2010.  Just 14 months into the marriage, Brand filed for divorce via text message and never spoke to Perry again.

What other celebrities do you think date out of their league? Comment below.