19 Celebrity Couples You Never Knew Dated

Just when you thought you’d figured out the tangled web of Hollywood relationships, we’re here to confuse you all over again. Though there are moments we’ll never forget, like Gwyneth Paltrow and Chris Martin’s “conscious uncoupling” or Kim Kardashian’s 72-day marriage, there are others that have seemingly slipped right through the cracks. 

Did you know Nicole Kidman was once set to become the step mother to Zoë Kravitz? Or that Kate Hudson once dated the ex-fiancee of Jennifer Lopez? Nope, neither did we. Some relationships we simply forgot about over time, while others kept their flings so low-key we missed them altogether. At least until now, where our extensive internet sleuthing has brought them back to light.

Keep scrolling for 19 celebrity couples you most likely never even knew dated…

Chris Evans and Jessica Biel

Before her marriage to Justin Timberlake, Jessica Biel was once coupled up with Captain America, Chris Evans. 

Kate Hudson and Alex Rodriguez

Way, way back in 2006, Alex Rodriguez AKA A-Rod, AKA JLo’s ex-fiancee, was in a serious relationship with Kate Hudson. So serious that Kate took Goldie Hawn and Kurt Russell to watch his baseball games as a family.

Drew Barrymore and Christian Bale

It was a teenage romance that never made it past the first date. Speaking to GQ Australia, Christian said, “we went to see some bloody awful horror film, and that was the end of it. She never called again!” Drew’s response? “He was so nice, I wasn’t like super boy crazy. I had a lot of fish to fry,” she admitted on Watch What Happens Live. “Like I had big problems in my world for many years, like in good ways. Things you gotta overcome. Boys are like very secondary.” Amen sister.

Janet Jackson and Matthew McConaughey

Alright, alright, alright, here’s another celeb coupling we simply do not remember. After meeting at the 2002 Grammys, Matthew was spotted leaving Janet’s house the next morning (carrying his shoes). A few years later, Janet told The Telegraph, “I guess we did [date]. He is such a great guy and a sweetheart. It was just for a minute, that’s why I’m so hesitant to mention it.”

Cher and Tom Cruise

Yes, you read that correctly. Not only did the pair date in the ‘80s, but during an interview with Andy Cohen, Cher revealed that Tom Cruise was among her top five best lovers. We’d love to know the other four…

Helen Mirren and Liam Neeson 

Reuniting on The Graham Norton Show years after their relationship had come to an end, Liam and Helen spoke openly of their past romance. “We didn’t date, we lived together for four years – we were a serious item for awhile. Lucky me,” she said. Aw.

Nicole Kidman and Lenny Kravitz

You know how Nicole and Zoë Kravitz both starred alongside each other in Big Little Lies? Well, it turns out their close bond didn’t start on set. Nicole was once set to be Zoe’s step mum. Yep, that’s correct. Lenny Kravitz and Nicole Kidman were once engaged, but split in 2003. During a press conference for Big Little Lies, Nicole said, “I knew Zoë because I was engaged to her father,” squashing speculation of any awkward feelings. “It’s all in the family! I love Lenny. He’s a great guy,” she added. Wild!

Tyra Banks and Seal

Well, Seal does have a type – supermodels. Prior to marrying Heidi Klum, Seal was an item with Tyra in 1996.

Liv Tyler and Joaquin Phoenix 

These two cemented themselves as one of the ‘it’ couples of the ‘90s, dating from 1995 before calling it quits in 1998.

Alanis Morissette and Ryan Reynolds

After meeting at Drew Barrymore’s 2002 birthday celebration, the couple announced the news of their engagement two years later. However, three years later, they ended their engagement. Speaking of the breakup to the L.A Times back in 2008, Alanis said “I was a full blown love addict, so it was like, ‘I can’t keep doing this, my body can’t take it’. For someone who is a love addict, [breakups] are debilitating.”

Cindy Crawford and Richard Gere

A 22-year-old Cindy met 39-year-old Richard at a mutual friend’s BBQ in 1988. After getting married in a Las Vegas ceremony in 1991, the famous couple announced their divorce four years later.

Salma Hayek and Edward Norton

Salma and Edward dated from 1999 to 2003 after being set up by their chiropractor. Who knew they were so proficient with matters of the spine… and heart. Sorry, we had to.

Ryan Gosling and Sandra Bullock

Following their meeting on the set of Murder By Numbers in 2002, these two dated for a year. Though the relationship was short-lived, Ryan has since assured us that it’s only good vibes between the exes. 

Ashton Kutcher and January Jones

Do you remember your first boyfriend? Because January Jones sure can. Despite looking like the perfect couple, January revealed that Ashton didn’t support the Mad Men star’s career aspirations – awkward. “[He] was not supportive of my acting,” she told GQ in the November 2009 issue. “He was like, ‘I don’t think you’re going to be good at this’. So, f***k you!”

“He only has nice things to say now,” she continued. “If anything I should thank him, because the minute you tell me I can’t do something, that’s when I’m most motivated.” Okay, thanks Ashton?

Cameron Diaz and Jared Leto

What began as a secret fling, blossomed into a four year romance. We know Cameron and Benji Madden are happily married now, however, we can’t help but wonder what could’ve been between this pair. 

Jenna Dewan and Justin Timberlake

After Justin split with Britney and long before Jenna ever married Channing Tatum, Jenna and JT were an item. The Step Up star met Justin while working as a backup dancer on his tour, before briefly testing the waters as a couple. During an interview on Watch What Happens Live Jenna said, “we dated, not that long. We were like friends..that dated.”

Leonardo DiCaprio and Gisele Bundchen

Before Gisele married Tom and Leo went on to date a gorgeous line-up of ladies, these two were an item for five years. Which is two lifetimes in Hollywood years.

Natalie Portman and Jake Gyllenhaal

Though this brief coupling didn’t work out, the two remain friends. Years later in 2011, Jake presented Natalie with the Desert Palm Achievement Award and joked “she’s a vegan, which makes it really frustrating when you’re picking a place to eat.” Perhaps this strained the relationship…

Sarah Jessica Parker and Robert Downey Jr.

This was no minor fling; these two dated for almost seven years. However, it was Robert’s addiction that led the relationship to breakdown. Speaking to Parade, the Iron Man star revealed, “I liked to drink and I had a drug problem, and that didn’t jibe with Sarah Jessica because it is the furthest thing from what she is.” 

Which of these past celebrity couples were you must surprised about?