Some Hollywood couples look absolutely perfect together, like Jessica Biel and Justin Timberlake, Blake Lively and Ryan Reynolds, and Mila Kunis and Ashton Kutcher. But not all famous couples look like they belong together, like Hugh Hefner and his bevy of young and beautiful girlfriends. Prior to marrying Crystal Harris in 2012, Hef moved 18-year-old twins, Kristina and Karissa Shannon, into the Playboy Mansion. The ladies appeared alongside Hef on the E! show “The Girls Next Door,” and everyone was shocked and a little disgusted by the 63-year age difference between the Shannons and their elderly boyfriend.
Another odd couple that made us cringe was Michael Jackson and Lisa Marie Presley. These two had a really hard time convincing everyone that their romance was anything more than a publicity stunt. Michael Jackson and Lisa Marie Presley claimed they had a lot in common due to their musical backgrounds, but their chemistry was just off, and their interactions seemed forced. When they shared an awkward kiss at the 1994 MTV Video Music Awards, we couldn’t help but to cringe.
Probably the most famous skin crawling romance of all-time is the marriage between Woody Allen and his step-daughter, Soon-Yi Previn. During his relationship with actress Mia Farrow, Woody had an affair with Soon-Yi, who is Mia’s adopted daughter. Although Woody and Soon-Yi aren’t blood relatives, we can’t help but to feel extremely awkward whenever we see them together. Aside from the fact that there’s a 34-year age difference between the two of them, many people can’t get over the fact that Woody not only had an affair, but eventually ended up marrying Soon-Yi 1997.
We all couldn’t help but laugh and look in horror as supermodel Brigitte Nielsen hooked up with rapper Flavor Flav on the reality show “The Surreal Life.” Sparks flew right before our eyes despite their backgrounds and their drastic height difference. It seemed to really work for them for awhile, but it left us all scratching our heads in confusion.
Sandra Bullock is America’s sweetheart and the leading lady in some of the most memorable romance comedies. When she hooked up with motorcycle customizer Jesse James, we all asked, “What does she see in him?” The two couldn’t look anymore different, with Sandra looking glam and elegant at all times, and Jesse having a more rough and rugged appearance. We definitely thought she could do better, and we were right. Jesse was later exposed for cheating on Sandra with multiple women, and the couple later filed for divorce.