15 Celebrity Couples You Won't Believe Used to Date

Many of you might have been shocked by the recent reminder that Mila Kunis and Macaulay Culkin dated for eight years. He was a huge star back in the 90s compared to Kunis whose fame began to rise after appearing in That '70s Show and voicing the character “Meg” on Family Guy. They managed to keep a very low profile since media outlets failed to make a big fuss about their relationship back then. Granted, this was in the days before hot social media tools such as Twitter existed. These days, if someone so much as bats an eye at someone (I’m looking at you, Hiddleswift), Twitter goes into overdrive. Besides the shock of their long lasting relationship, they seemed a little mismatched, very different from one another. As fans on the outside looking in, we just don’t get some couples because they appear to be polar opposites (due to age, celebrity status, etc.) while others make more sense at the time.

For various reasons celebrity relationships inevitably come to an end and it becomes a distant memory, fading from our collective consciousness. Until now that is. This is a reminder of celebs who you likely forgot (or didn’t even know) dated. Many dated before they became mega superstars and for the most part they’ve all matured since their ill-fated romances. They can look back on their past relationships with fondness (in some cases) and in others they can see the lessons they’ve learned since then.

15 Brad Pitt and Thandie Newton


Many of you might be surprised to know that these two dated back in 1994. They met on the set of their movie Interview with a Vampire (you’ll notice a popular trend throughout this list, co-stars who date). Dating at the time (whether after filming is complete or during it) makes sense since actors spend so many months working together, you get to know someone really well. While their relationship only lasted a year (their split is said to have been an amicable one), their friendship has endured the test of time. This is great because they both seem like genuine, down to earth people (this observation is based purely on tabloid fodder and could be wrong, but let’s ignore that and say it’s true). Pitt is now a father of six and married to Angelina Jolie while Newton is a married mother of three. Both have done really well for themselves since they were co-stars in Interview with a Vampire. They’ve each become A-listers, appearing in many hit movies over the years.

14 Jon Cryer and Demi Moore


In a weird twist of fate, before Aston Kutcher met Demi Moore and before he starred in Two and a Half Men with Jon Cryer, Cryer actually dated Moore. Cryer and Moore appeared together in 1984’s No Small Affair. This was long before the age of social media so it didn’t become public knowledge until Cryer discussed it in his memoir So That Happened, released in 2015. When Kutcher went to a “chemistry meeting” (aka deciding whether actors can play nice together) with Cryer back in 2010, it wasn’t clear if Kutcher knew about this little bit of history. He was married to Moore by then. While the two actors obviously hit it off (Kutcher later joined the cast), Cryer couldn’t help feeling a little awkward about the whole situation initially. Cryer and Moore have moved forward since then, Cryer is married to Lisa Joyner (you might have seen her in TLC’s Long Lost Family) and Moore and Kutcher officially divorced in 2011.

13 Jared Leto and Cameron Diaz


Before she dated Justin Timberlake (aka JT) and married Benji Madden, Diaz was head over heels for Leto. The couple dated for four years and were even engaged in 2000. So, what happened? It seems that by 2003 they were both in a place where they wanted to focus more on their respective careers than the relationship. This makes sense because that same year Diaz starred in Charlie's Angels: Full Throttle and her star has only continued to shine since then.

Let’s face it, celebrities have to juggle a lot when it comes to their careers and their relationships can suffer as a result. Look at Lady Gaga and Taylor Kinney. Both were highly committed to each other but are just as committed to their careers. Anyway, Leto has gone on to enjoy his own success and most recently donned “The Joker” mantel for the highly anticipated Suicide Squad movie.

12 Brad Pitt and Gwyneth Paltrow


They were the “It” couple back in the '90s. They even became known for their penchant for wearing matching hairstyles. Paltrow and Pitt dated for two and a half years after they met on the set of their movie Seven in 1995. They were engaged the following year but ultimately called off the wedding in 1997. Paltrow didn’t feel she was mature enough for the relationship at that time. After all, she was only 22 when they started dating so she felt as though she was much too young to be in such a serious relationship. She’s even gone as far as to say that he’s the one that got away. She’s even said that her late father, Bruce Paltrow, was also close to Pitt and was sad to see the relationship end.

While they haven’t kept in touch over the years, they’re still friendly if they run into each other. They both moved on to other relationships (Paltrow’s divorce…sorry, uncoupling from Chris Martin is now final) and they’ve become super successful actors.

11 Matt Damon and Minnie Driver


Before his wife Luciana Barroso stole the show with her style sense at a recent Jason Bourne screening, Damon was romantically linked to Driver. They both starred in the hit movie Good Will Hunting in 1998 and started dating soon afterwards. The relationship ended when Damon publicly denied having a girlfriend while making an appearance on The Oprah Winfrey Show (ouch!). This very public breakup was no doubt a surprise to Driver. She’s gone on to say that it was highly inappropriate on his part and very hurtful for her. Whatever caused the breakup is a mystery to us all but she wishes that they could have remained friends.

Damon (aka The Martian) is now a happily married father of four and Driver is working hard to re-establish herself as an A-lister. She’s also mom to a 7-year-old son.

10 Chris Evans and Jessica Biel


Before she became Mrs. Timberlake, Jessica Biel dated Chris Evans (aka Captain America) for five years (from 2001 to 2006). Like many of the couples on this list they’ve also worked together. They both starred in 2004’s Cellular and 2005’s London where they played couples who ultimately experienced bad breakups. While Evans has gone on to date a long list of leading ladies (he’s rumored to have dated Naomie Harris from the recent James Bond movie franchise in 2008 and Sandra Bullock briefly back in 2014), he’s now in a relationship with Jenny Slate. They met on the set of Gifted (coming out in 2017). Side note, she’s the voice of “Gidget” in the 2016 movie The Secret Life of Pets. Biel and Timberlake have a son and are still enjoying wedded bliss. They’re currently gearing up to start planning for their second child.

9 Nick Lachey and Kim Kardashian


These two dated very briefly back in 2006 after Lachey’s very public breakup with Jessica Simpson. Kardashian was relatively unknown at the time so he was a little freaked out that the paparazzi showed up after their movie date. His guess is she tipped them off during their date so they’d have pictures to take showing her out and about with a high profile celebrity. Who knows if that’s true but what we do know is that at the time he was still at the height of his career as a member of the group 98 Degrees. He understandably he felt that she’d used him for his fame. Whether or not that’s true she was able to catapult herself into super stardom not long afterwards. This is supposedly the reason her five-month romance with Nick Cannon ended. She lied about the existence of a certain tape. Lachey is now married to Vanessa Lachey with whom he shares two kids. We all know how things turned out for Kardashian.

8 Joseph Gordon-Levitt and Meagan Good


This one may come as a shocker because these two are so different from one another, based on their dating history up to this point. Regardless of this, these two dated very briefly (I’m talking six months) back in 2005. They, like most other celebrity couples, met while working together on the independent film Brick. Unfortunately, the relationship ended very badly with Gordon-Levitt calling her fake and Good hurling just as insulting accusations his way. Fortunately for Good, she’s moved on and is now happily married (since 2012) to film producer and motivational speaker DeVon Franklin. He’s also an author and together with Good they recently wrote and published The Wait which is an inspirational book that in part chronicles their relationship. Like Ciara and Russell Wilson, they chose to abstain before their marriage. Gordon-Levitt is also happily married and is enjoying his new role as dad.

7 Ben Affleck and Gwyneth Paltrow


Unlike her relationship with Brad Pitt, Paltrow has confessed that her relationship with Affleck suffered from the many low points they experienced. Their relationship started after they co-starred in the 2000 movie Bounce. She’s confessed that he wasn’t in a particularly good place in his life back then. He’s dealt with alcoholism and gambling and has come out on top. It’s no doubt difficult to commit successfully to a relationship when there are other options (albeit very unhealthy ones) competing for attention. The addictions won out and the relationship suffered. It’s no surprise that they haven’t stayed in touch much since their breakup. But what may be considered surprising is that Paltrow and Jennifer Garner have spent time together in the past. Paltrow has said that they get along very well and that she admires Garner.

6 Robert Downey Jr. and Sarah Jessica Parker


Another surprise union, these two dated for seven years (after starring together in the 1984 film Firstborn) before they called it quits. His drug and alcohol addiction played a part in the split because he’s admitted that while she was the conservative down to earth one, he was too much to handle at the time. Like any good girlfriend she hung in there and tried to help as best he could. Eventually his addictions took over and he spent some time in rehab and in jail. However, he’s been drug free since 2003 and they’ve both moved onto healthy, successful marriages. Both have three children each and as you know, he’s now Iron Man!

Last year they were able to meet up and bury the hatchet and bring closure to that time in their lives. Even when a relationship ends very badly it’s so refreshing to see that individuals can come together and move on as friends and let the past stay in the past.

5 Ryan Gosling and Sandra Bullock


These two met on the set of their 2002 movie Murder by Numbers. Despite their 16-year age gap they hit it off and dated for a year. They were both well known actors at the time but Bullock was without a doubt the most famous of the two at the time. Alas, it wasn’t meant to be so when the relationship ended he moved on to date Rachel McAdams and starred in The Notebook where he gained his heartthrob status. Since he and Bullock dated, he’s stated that she was one of his greatest girlfriends. It’s so good to hear when exes have positive things to say about one another instead of cutting each other down.

Gosling is now in a committed relationship with Eva Mendes and they have two kids together. Bullock may have found “the one” since her divorce from Jesse James. She’s dating photographer Bryan Randall and has two children of her own.

4 Jake Gyllenhaal and Kirsten Dunst


While his relationship with Reese Witherspoon might be more familiar with most folks, Gyllenhaal also dated Kirsten Dunst for two years after meeting her in 2002. They were both very sought after actors during their time together (Gyllenhaal more so now) so work kept them apart and their relationship ended in 2004. Like a few other couples on this list they both look back fondly on their time spent together. Although Dunst confirmed in a 2009 magazine interview that while it would be nice to see him again they’re not friends. They haven’t kept in touch since they broke up. While Gyllenhaal has had his fair share of relationships over the years (he’s even dated Taylor Swift who’s rumored to have penned a few songs about their relationship on her Red album); he’s still searching for “the one”. Dunst is rumored to be dating her Fargo co-star Jesse Plemons.

3 John Mayer and Taylor Swift


These musicians dated for a year after working together on a track called "Half of My Heart," for Mayer’s 2009 album Battle Studies. After they broke up she returned the favor and he’s said to be the inspiration behind her song “Dear John.” Needless to day, Mayer wasn’t too pleased with how it portrayed him. The lyrics took him by surprise because Swift had previously not revealed her true feelings about the end of their relationship to him. Mayer and on-again, off-again girlfriend Katy Perry have finally called it quits and after a string of failed relationships, Swift has settled in comfortably with Tom Hiddleston. Here’s hoping her new guy is ready to stand by her side as she contemplates whether or not to take on Kimye in her latest round of drama. Fighting words have been issued so let’s sit back and see where this goes.

2 Tom Cruise and Sofia Vergara


OK, pick your jaw up from the floor with this one. Yes, it’s true, Cruise and Vergara dated briefly back in 2005 after being introduced by Will Smith. Scientology was the rumored reason for the downfall of their relationship. After visiting the church’s Celebrity Centre and being introduced to church leader David Miscavige, Vergara realized that she would have had to give up her Catholic beliefs and officially convert to Scientology. Being a strict Catholic this option didn’t appeal to her and the relationship ultimately fizzled.

Since starring in Modern Family, Vergara has gone on to become a mega celebrity in her own right. Cruise was linked to a few other ladies after this short lived romance but it was Katie Holmes who eventually won his heart. They were married for five years before she moved to end the marriage. Vergara is now happily married to Joe Manganiello.

1 Wilmer Valderrama and Mandy Moore


Before his long-term relationship with Demi Lovato, Valderrama dated Moore for a year (from 2001 to 2002) after she appeared on his hit TV show That '70s Show. When the relationship ended, he boasted about “stealing her virtue” which she adamantly denied and referred to as tacky on his part. They’ve since mended their friendship and even recently posed together for a selfie while at Paramount Studios. Again, kudos to exes who can remain friendly. They both shoot TV shows at Paramount Studios which is why they’re likely to continue encountering each other in the future. Mandy is starring in This Is Us while Valderrama is now a season regular appearing in the upcoming 14th season of NCIS.

Moore finalized her divorce from Ryan Adams in June 2015 and has since moved on to date Taylor Goldsmith. Valerrama is currently single after he and Lovato suddenly ended their six-year relationship.

Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

15 Celebrity Couples You Won't Believe Used to Date