Olivia Wilde and Harry Styles
When fans saw Olivia and Harry going hand in hand during a January 2021 wedding, they had to make a double take. The duo is still going strong; most recently, the Booksmart director was seen costumed as Dolly Parton and supporting the former One Direction member at his Harryween event.
Pink and Joey Fatone
According to the former member of NSYNC, "We left the house. We were as laid-back as they come. But I think I wasn't her kind of girl."
Ashley Olsen and Lance Armstrong
Lance's pals advised him to break up with Ashley due of their 15-year age difference back in 2007.
Michelle Rodriguez and Zac Efron
While their PDA-filled trip to Ibiza in 2014 made headlines, the Fast & Furious star only dated the Disney vet for two months.
Madonna and Dennis Rodman
Their high-profile 1994 affair lasted barely two months, but it was a roller coaster ride to say the least.
Fergie and Justin Timberlake
Fergie claims she had a relationship with a young JT when on tour with NSYNC in the late 1990s with her band Wild Orchid. Because Fergie revealed that Justin was 16 and she was 23, the connection was clearly inappropriate and potentially illegal.
Bella Thorne and Scott Disick
Let's be honest, most of Scott's dating history is shocking outside of Kourtney Kardashian, but his connection with Bella had me saying, "Wait, what?!" During the spring and summer of 2017, they had a brief romance.
Naya Rivera and David Spade
In 2017, the late Glee star and comedian had a spring romance. When they first saw the two making out at the Halekulani Hotel pool in Waikiki, Hawaii, onlookers were taken aback.
Nicole Kidman and Lenny Kravitz
Lenny was Nicole's landlord when they initially started dating in 2002, believe it or not. Later on, the two became engaged. Nicole explained why they never married, "I wasn't ready." We weren't prepared.... That's my thing: I get engaged and married. I'm not interested in dating.
There is 2Pca and Madonna on the left and Tom cruise and
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