2020 has offered us its fair share of unexpected Hollywood romances — Bill Hader and Rachel Bilson? Ben Affleck and Ana de Armas (pictured)? Machine Gun Kelly and Megan Fox? But, all of these seem perfectly normal compared to some other couples that have rocked Hollywood with just how bizarre they are.
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Zac Efron was 26 and Michelle Rodriguez was 36 when they dated back in 2014. The age difference alone raised a few eyebrows, though the couple seemed unbothered by people’s opinions, packing on the PDA whenever they could. But, the whirlwind relationship only lasted two months.
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Macaulay Culkin and Mila Kunis dated for a whopping eight years. The couple were pretty private about their relationship, which lasted from 2002 until 2011. In 2018, Kunis opened up about the end of the relationship on Dax Shepard’s podcast, saying it was a “horrible, horrible break-up”: “I [expletive] up.” Kunis is now married to Ashton Kutcher while Culkin is dating Brenda Song.
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It’s probably the least likely couple on the planet, but it’s true — Tom Cruise and Cher dated in the ‘80s, despite their 22 year age gap They met at Sean Penn and Madonna’s wedding in 1985, and again at a White House event where there was “definitely a connection”, though they began dating “way later,” according to Cher. “A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic,” she said. Apparently they’re still friends, but Cher admits she doesn’t “get” the whole Scientology thing.
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Lovebirds Ryan Reynolds and Alanis Morisette hit it off back in 2002 and were engaged by 2004, holding the potential to be one of Canada’s biggest power couples. They met the way we all dream of meeting — at Drew Barrymore’s birthday party. But the passionate duo lost their spark after nearly three years of being engaged.
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He was a TV star, she was a pop rock icon — can I make it any more obvious? From 2010 until 2012, Brody Jenner (Kendall and Kylie’s half-brother) dated singer Avril Lavigne, and according to paparazzi images featuring their unfortunate style choices back in the day (no judgement, we weren’t any better), they were inseparable for quite some time.
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One of the most long-lasting unexpected relationships in the history of Hollywood, Benji Madden and Cameron Diaz are still going strong today. The Good Charlotte singer and ‘Charlie’s Angels’ actress met in 2014 through Madden’s sister-in-law, Nicole Richie. They were married the next year. In January of 2020, they announced the birth of their daughter.
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Ryan Gosling and Sandra Bullock dated in the early 2000s. Two of the greatest actors of our time, the pair met on the set of their 2002 film ‘Murder By Numbers’ and apparently they were a romantic item for two whole years. They kept everything private, but later Gosling confirmed the rumour and called Bullock one of his “greatest girlfriends.” Miss congeniality, indeed!
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TV host Chelsea Handler met rapper 50 Cent on her show back in 2009, which spurred on a PDA-packed romantic relationship. Apparently, 50 Cent was so late to the show that Handler — who’s known not to mince her words — had a go at him. So, 50 Cent sent her a bouquet of flowers to her office everyday, until she finally started dating him.
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Dave Coulier, best known as Uncle Joey from ‘Full House’, dated singer Alanis Morissette in 1992. After they broke up, Morissette released her powerful Grammy Award-winning break-up song, ‘You Oughta Know’, which many believe was about her rough split from Coulier. However, Morisette keeps mum about it until this day!
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Before his redemption arc, John Mayer left a trail of devastation in his romantic life — and Jessica Simpson wasn’t exempt. Simpson made many damning claims about Mayer in her memoir — that he gave her Xanax because he felt she drank too much, made her feel like she wasn’t smart enough for him, and broke up with her nine times, including once by email. He also infamously described her by the derogatory term “sexual napalm” in an interview with Playboy. This is one relationship better left in the past.
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Iron Man and Carrie Bradshaw — who would’ve thunk it? Robert Downey Jr and Sarah Jessica Parker met in 1984 on the set of ‘Firstborn’, when they were 18 years old, and it took them only eight weeks to move in together. They stayed together for nearly eight years before calling it quits in 1991. According to RDJ, his substance abuse problems “didn’t jibe with Sarah Jessica, because it is the furthest thing from what she is … I was in love with Sarah Jessica … and love clearly was not enough”.
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Nick Lachey and Kim Kardashian weren’t exactly boyfriend and girlfriend — but they did go out on a date. The 98 Degrees singer and reality TV star wouldn’t call her his “ex”, but they did go on a single date together to see ‘The Da Vinci Code’ in 2006. In Hollywood, some might even consider that a long-term relationship.
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Brad Pitt and Christina Applegate were set to go on a date to the 1989 MTV Movie Awards, but Applegate was the one who got away. She ditched Pitt for another man, who she says wasn’t an actor but was publicly know. However, Skid Row singer Sebastian Bach claims to be the mystery beau.
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Both Jessica Biel and Chris Evans are cagey about their private lives, so it comes as no surprise that there’s little known about how they met. The two actors dated on-and-off between 2001 and 2006. They once went skydiving together and on Biel’s 21st birthday, Evans scattered rose petals on her bed. Biel, of course, is now married to Justin Timberlake.
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Eclectic basketball player Dennis Rodman and pop diva Madonna were both bold, brazen and bizarre, so it makes perfect sense that they dated for two months back in 1994. Their story is as strange as it gets; apparently, when they met, Madonna locked Rodman in a hotel room and told him she wouldn’t let him out. The five-time NBA champion also claimed that Madonna offered him $20 million (Dh73.44 million) to impregnate her, which Madonna denies.
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Actress Lisa Kudrow, best known as Phoebe Buffay, and late night host Conan O’Brien briefly dated. Apparently, they met at an improv class before she broke out on the 1994 hit sitcom ‘Friends’. “He was really smart, really funny, and he thought I was funny,” Kudrow said. But, the pair found they were better off as friends.
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