7 Most Shocking Alleged Celebrity HookupsPublished on January 30, 2015. Updated April 3, 2017
Celebrities hookups make headlines all the time. When a relationship ends, at least one of the parties will be on the rebound, hunting around the city for their next prey. A lot of the time they end up hooking up with other celebrities and we usually hear about it. The only problem is that we never really get any confirmation – everything is shrouded in mystery. Because of this, we can only assume what happened, which can still be a lot of fun. We have tracked down 7 of the most shocking alleged celebrity hookups in Hollywood history. Some have said that it never happened, but there is enough evidence there to suggest something probably did!
7. Ashley Olsen and Jared Leto
Ashley Olsen and Jared Leto were rumored to have dated back in 2005. She was still a teenager at the time while he was in his mid-30s. It didn’t last, which was to be expected. In 2008, however, they were spotted out together, acting very much like a couple. There was reportedly hand holding and kissing. Insiders squashed claims that these two were anything more than friends though; however, the same thing ended up happening again in 2012. Olsen and Leto were acting like they were together. They were spotted out enjoying a romantic meal, which again included physical affection and lip locking. Again, it didn’t last.
Leto seems to be quite the player. Since breaking up with Cameron Diaz in 2003, he has not settled down again. He’s been linked to a number of different of different high profile women though, including Lindsay Lohan, Paris Hilton, Miley Cyrus and Katy Perry.Featureflash / Shutterstock.com Helga Esteb / Shutterstock.com
6. James Franco and Lindsay Lohan
Last year, a list of men Lindsay Lohan had reportedly bedded was leaked to In Touch Weekly. She later confirmed that it was in fact real and that someone had stolen it and sold it to the magazine. One of the names on the list was James Franco. He has denied that he ever slept with her and has gone so far as to say that she is delusional. For years now, many of us have questioned whether or not Lohan is actually with it psychologically; however, we don’t really see why she would lie about this particular hookup. Franco isn’t even that hot.
The “Pineapple Express” star had admitted to kissing the troubled starlet. According to him, she would practically stalk him when they were both staying at the Chateau Marmont and, on one occasion, she actually broke into his room while he was sleeping. We’re guessing that these two did hook up and it wasn’t especially memorable – at least for him.Joe Seer / Shutterstock.com Everett Collection / Shutterstock.com
5. Britney Spears and Fred Durst
Back in 2003, Britney Spears and Fred Durst allegedly had a hot affair. While he had no problem sharing his feelings for her with the world, she denied ever having hooked up with him. In 2009, he told MTV News that he had been honest about their relationship. “It just became a fiasco of madness,” he said. “[But] I always stay true to my heart and true to everything I did and my intentions, and I am in no way a liar.”
According to Spears, the relationship was one-sided. “I think him for me, but not me for him,” she told Glamour magazine. “He’s said some pretty amazing things about me. But, um, I think he leaped in too deep, too quick.” She was probably still missing Justin Timberlake at that point and we’re pretty sure that whatever she had with Durst was nothing but a rebound. Around that same time, she was also caught smooching Colin Farrell.Helga Esteb / Shutterstock.com s_bukley / Shutterstock.com
4. Topher Grace and Vanessa Minnillo
Topher Grace and Vanessa Minnillo were reportedly spotted dancing and making out at a party at Seth MacFarlane’s house back in the summer of 2009. Reports say the two left the party together at the end of night too. She had just broken up with Nick Lachey and it looked like she was on the rebound. We’re guessing that it was probably just a little fling that lasted for just one night because, within two months, she was back in Lachey’s arms, telling people that she had only been single for a minute.
At the end of the summer, Minnillo and Lachey were spotted hanging out, making out and acting very much like a couple at the Dime bar in Los Angeles. A few months later, he announced that they had patched things up and that the relationship was back on. A year later, he popped the question and now they are married with two children, a boy and a girl.Helga Esteb / Shutterstock.com Jaguar PS / Shutterstock.com
3. Rihanna and Ashton Kutcher
Rihanna and Ashton Kutcher were rumored to be hooking up back in 2012. This wasn’t long after his marriage to Demi Moore imploded. The fling lasted for a reported eight weeks. There wasn’t much evidence for the relationship except for the one night that she was spotted visiting his house from midnight until 4 A.M. Shortly after this, Kutcher hooked up with Mila Kunis and the rest is history.
When it comes to men, Rihanna has certainly made a number of questionable choices. She has reportedly been hooking up with Leonardo DiCaprio for years. They were both spotted ringing in the New Year in St. Barts on P. Diddy’s yacht this year. When they got back to Los Angles, they attended the same party at the Playboy mansion. Sources say that these two aren’t looking for any kind of commitment and are just having fun. The only thing we know for sure is that Rihanna obviously has bad taste in men.Joe Seer / Shutterstock.com Helga Esteb / Shutterstock.com
2. Sienna Miller and P. Diddy
Back in 2007, everyone was talking about Sienna Miller and P. Diddy. These two claimed that they were just friends, but it looked like they were a little more than that. They were spotted getting cozy at a Sundance party and then a couple weeks later he was seen dropping her off at her hotel in New York City in the early morning after a night of partying together. Diddy was still with Kim Porter at the time. She had recently given birth to his twins and rumor has it that they had more of an open relationship. He cheated on her regularly and she turned a blind eye to it.
Miller wasn’t the only A-list actress Diddy allegedly hooked up with. Back in 2008, he reportedly had a secret affair with Cameron Diaz, which continued on an on-again, off-again basis for another few years. He’s a pretty lucky guy – all of his ladies are super hot and desirable. How does he swing this?Everett Collection / Shutterstock.com Everett Collection / Shutterstock.com
1. Justin Timberlake and Jenna Dewan
After he split from Britney Spears, Justin Timberlake reportedly jumped into a hot rebound relationship with Jenna Dewan. Rumor has it that Timberlake and Dewan were at a club one night when Spears walked in. They were dancing together and she got pretty jealous. When he went to go get drinks, she confronted him, accusing him of using Dewan and other women to get media attention. This all led to a dance off between Spears and Timberlake. Poor Dewan. She probably was nothing more than a rebound.
The two pop stars had a pretty messy breakup. She reportedly cheated on him with Wade Robson, her choreographer for her Dream Within a Dream Tour. This led him to record a song and video about their breakup, which featured a Spears lookalike cheating on him. Timberlake obviously didn’t take the breakup especially well, which is why we think he used Dewan.s_bukley / Shutterstock.com Helga Esteb / Shutterstock.com