24 Celebrities Who Were Rumored to Have Hooked Up: From John Stamos and Demi Moore to Will Smith and Jennifer Lopez

Ben Stiller and Brandi Glanville was the couple Hollywood almost had.

The former Real Housewives of Beverly Hills star detailed her hookup with Stiller during her appearance on Danny Pellegrino's podcast, praising the Night at the Museum star's big load.

"As far as the Denise [Richards] stuff, because I was given a cease and desist, I'm gonna just not talk about it until I have to," she said of their fling.

Brian Austin Green told his side of the story about his rumored fling with his former costar Tori Spelling when talking to Andy Cohen during an episode of Watch What Happens Live.

"We hooked up. We did. We were young, and so, that's what young people do," he admitted.

In Elliot Page's memoir, Pageboy, the Umbrella Academy star revealed the secret romance he and Kate Mara shared in the past. He wrote that they met at a small dinner party before coming out as a trans.

"The first person I fell for after my heart was broken was Kate Mara. She had a boyfriend at the time, the lovely and talented Max Minghella," Page continued. "I never thought I could be in love with two people and now I know I can."

The pair's connection did not last long, though Page considered it as a part of "a difficult pattern" he experienced.

Before marrying the Prince of Darkness Ozzy Osbourne, Sharon Osbourne exposed in an episode of The Talk that she had a fling with Jay Leno.

"I come down to this club and it is full of men performing and this one person I think, said, 'Oh he's very nice, very funny.' So I said to my friend, 'I like him,'" she said.

Sharon eventually met the 73-year-old TV host and had a short-lived connection with him. Months after their "flingy wingy," Leno introduced her to the real love of his life.

Decades after they appeared in the 1980s hit General Hospital, John Stamos detailed his relationship with Demi Moore in his memoir.

Titled If You Would Have Told Me, the book shared that the pair reconnected at a party in honor of Jamie Lee Curtis' 2023 Oscar nomination for Everything Everywhere All at Once. Ali Adler reportedly gushed about them at the event.

"We both look at each other, wondering what the other will say. Demi pauses to think about it. 'I don't know if we slept together. I think we fooled around though,'" Stamos recalled.

In her interview with Cosmopolitan, Fergie talked about her romance with Justin Timberlake in 2016 while reiterating that she never had a one-night stand with anyone.

"One of my good friends was dating J.C. Chasez, and so we'd all hang out with *NSYNC. Justin and I would go out together and have fun and make out," she said. "We went to Hawaii together, but we were never serious. He was Mr. Right Now."

The "Just Can't Get Enough" singer previously said she did not want to make a big deal out of their fling because it was not anything serious.

After Lance Bass came out in 2006, the *NSYNC member was linked to different men, including Cohen. The LGBTQ advocates reportedly hooked up and only spoke about it in 2012.

"Now it's getting into who did who? I can just tell you right now, there was no Andy D going in my B," Bass said. "I'm not going to tell you what went down… but it's not what people are thinking."

Before Leonardo DiCaprio started his streak of dating younger women, he sparked dating rumors with Naomi Campbell when they attended events before the release of Titanic. Their brief fling made them realize they were better off as friends.

During an appearance on The Kelly Clarkson Show in 2019, Mario Lopez gushed about hooking up with his Saved by the Bell costar — particularly Tiffani Thiessen.

The America's Best Dance Crew host, who wed Courtney Mazza in 2012, said he enjoyed a "real romance" with his former castmate.

"It's funny, 'cause I went to regular high school and she used to wear my letterman's jacket from my real high school and stuff," he shared. "But now, she's my dear friend and it's funny 'cause our kids actually play together. So, we'll get together, our kids play together and stuff."

Matthew McConaughey and Janet Jackson had an almost love story when they hit it off at the Grammy Awards in 2002 and dated afterward. Although they eventually dismissed the dating rumors, the "Escapade" singer seemingly confirmed their hookup in 2006 in her interview with Upscale Magazine.

In 1987, Nicolas Cage and Brooke Shields had a brief hookup after her relationship with Dodi Fayed, Princess Diana's love interest until their deaths in August 1997.

Jennifer Lopez would have had her own entanglement when Will Smith and Jada Pinkett Smith tried to hook up with her in the past.

Diddy's former bodyguard told The Art of Dialogue that the event happened at a birthday party for Ben Affleck at the Four Seasons.

"Matt Damon, Ben Affleck, Jennifer Lopez, Puff, Will Smith and Jada were sitting on [one] side of the room," bodyguard Gene Deal said. [Puff] stood up. And when he stood up, he walked and did his arms a certain kind of way like [crossing them]. I go over towards him and he said to me, 'Yo, I think Will and Jada are trying to scoop up Jennifer. I want you to stay close 'cause I'm a snuff him.'"