Celebrity Couples That Didn’t Make Sense

Most celebrities want to be known for their talent and accomplishments. Unfortunately, most people remember them for who they dated and how the relationship ended. When two big stars get together, it is usually a media frenzy. The world wants to know everything about them, but publicity drives them apart.

Ryan Gosling (co-star of film) and Sandra Bullock
Photo by Jody Cortes/Sygma/Sygma via Getty Images

Some celebrities hope people will forget about their past romances, but they are mistaken. With just a few strokes on the keyboard, anyone can pull up a star’s dating history. You might have forgotten about these odd celebrity couples, but we are here to refresh your memory. Take a look back at famous couples that didn’t make sense.

Nicole Kidman and Lenny Kravitz

Nicole Kidman is not one to be afraid of PDA with her husband, Keith Urban, whenever they are in public or on a red carpet. However, before she married the country singer, Kidman was once engaged to Lenny Kravitz. She must have a thing for musicians because Urban and Kravitz are music legends.

Recording artist Lenny Kravitz (L) and actress Nicole Kidman
Photo by Charley Gallay/Getty Images for dcp

Most people forget about their relationship because it is such an odd match. After her highly publicized split from Tom Cruise in 2001, Kidman began dating Kravitz, who was her landlord at the time. Kravitz proposed to Kidman in 2003, but she ended it because she wasn’t ready for marriage.

Sandra Bullock and Matthew McConaughey

After co-starring in A Time to Kill, Sandra Bullock thought Matthew McConaughey was “alright, alright, alright.” The two started dating shortly after filming, which people often forget because it’s hard to remember a time before he was with Camilla Alves. We can’t picture him with anyone else.

American actress Sandra Bullock and American actor Matthew McConaughey
Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images

However, McConaughey and Bullock dated for two years. When they split, the two were on good terms and spoke highly of each other to the press. In a 2003 interview, Bullock said, “No matter where he is in life or where I am in mine – he could be married – I know we would stay close.”

Ryan Reynolds and Alanis Morissette

Like McConaughey and Alves, Ryan Reynolds and Blake Lively are one of those couples that seem like they have been together forever. We can’t picture Reynolds with anyone but Lively. However, Reynolds and Alanis Morissette dated before he met the Gossip Girl star. It’s a very odd pairing, but they are both Canadian.

Ryan Reynolds and Alanis Morissette
Photo by Kevin Mazur/WireImage

Morissette and Reynolds met in 2002 and dated for a whopping four years. Reynolds even proposed to her, but the pair didn’t make it down the aisle. They realized they weren’t the right match and parted ways in 2006. Reynolds eventually moved on with Lively, and Morissette married Souleye in 2010.

Reese Witherspoon and Jake Gyllenhaal

In 2008, Reese Witherspoon and her first husband, Ryan Phillippe, divorced, leaving fans devastated for the Legally Blonde actress. But everyone rejoiced when Witherspoon reportedly started dating Jake Gyllenhaal. The two met on the set of 2007’s Rendition, and sparks began to fly as her marriage fell apart.

Reese Witherspoon and Jake Gyllenhaal
Photo by Chris Polk/FilmMagic

The two officially became a couple soon after her divorce. Witherspoon and Gyllenhaal made a cute couple and looked great in pictures. Unfortunately, the pair went their separate ways two years later. They would have had beautiful children, but it wasn’t meant to be. Witherspoon eventually married Jim Toth in 2011.

Mila Kunis and Macaulay Culkin

We couldn’t think of a more bizarre pairing than Mila Kunis and Macaulay Culkin. Considering how private Culkin is about his love life, it’s no wonder people didn’t know these two dated for eight years. The pair met in 2002 when Culkin wasn’t in the spotlight much.

Mila Kunis and Macaulay Culkin
Photo by Dimitrios Kambouris/WireImage

Kunis and Culkin tried to keep their relationship as private as possible, but fans would stop them on the rare occasions they were seen in public. Kunis said, “He was huge. You couldn’t walk down the street with him.” The pair parted ways in 2011 and found love elsewhere.

Leonardo DiCaprio and Gisele Bundchen

While Leonardo DiCaprio is known for dating models, Gisele Bundchen is out of his 25 and lower age range. Before she married Tom Brady, the model and DiCaprio dated on and off for six years. She wanted to settle down, but he wasn’t ready to give up his bachelor phase.

Actor Leonardo DiCaprio and girlfriend, model Gisele Bundchen
Photo by Vince Bucci/Getty Images

Bundchen and DiCaprio parted ways, but they made a beautiful couple. Maybe he will give it another shot now that Bundchen and Brady are divorced. DiCaprio is approaching 50, so he may be like George Clooney and finally settle down.

Blake Lively and Penn Badgley

Just like her now-husband, Blake Lively has also had other relationships. While other relationships on this list didn’t make much sense, we once rooted for Lively and Penn Badgley. The two Gossip Girl stars had an on-and-off on-screen romance that everyone wanted to succeed.

Actress Blake Lively and actor Penn Badgley
Source: Photo by Getty Images

When the two took their on-screen relationship to the real world, fans were ecstatic about the news. However, after three years together, the two broke up in 2010. Although they didn’t make it, their characters ended up together on Gossip Girl.

Bradley Cooper and Renee Zellweger

Bradley Cooper may be a Hollywood hunk, but he has been off the market since 2015, when he started dating Irina Shayk. Although the two broke up in 2019, fans have speculated that they might work things out. Regardless of their relationship, he was once involved with Renee Zellweger.

Renée Zellweger and Bradley Cooper
Photo by Kevin Winter/Getty Images

Cooper and Zellweger met on the set of 2006’s Case 39 but didn’t begin dating till 2009. There was plenty of media speculation about their relationship, but they refused to comment on it. They made several appearances together but broke up in 2011.

Lindsay Lohan and Samantha Ronson

After ending things with Wilmer Valderrama from That ‘70s Show, Lindsay Lohan started dating Hard Rock Café heir Harry Morton in 2006. Their romance was short-lived, and Lohan moved on with British DJ Samantha Ronson. Everyone was shocked to see Lohan with a woman because she never spoke about her sexuality.

DJ Samantha Ronson and Lindsay Lohan
Photo by Chris Polk/FilmMagic

Their high-profile romance lasted for about a year before they split in 2009. Lohan later commented on the relationship, saying, “Two toxic people cannot be together. End of story.” Their breakup was messy, involving changing locks and hurt feelings.

Angelina Jolie and Johnny Lee Miller

Angelina Jolie has made headlines several times for her relationship choices and scandals. But before she married Brad Pitt and Billy Bob Thornton, Jolie had a whirlwind romance with Johnny Lee Miller. The two met on the set of 1995’s Hackers and fell head over heels.

Jonny Lee Miller and Angelina Jolie
Photo by Gregory Pace/FilmMagic

After a year of dating, Jolie and Miller married in March 1996. The two were married for three years before divorcing in 1999. Within a year, Jolie had moved on to marry Billy Bob Thornton. Meanwhile, Miller married Michele Hicks in 2008.

Michael Keaton and Courteney Cox

Courteney Cox is best known for playing Monica Gellar on Friends and being married to David Arquette. Before she was one of the highest-paid actresses, she dated Michael Keaton. The two were an odd pairing because of their 13-year age difference.

Michael Keaton and Courteney Cox
Photo by Barry King/WireImage

Keaton and Cox started dating before she got her big break, and lasted for six years. The two ended things in 1995 as her career took off. She later went on to marry Arquette, and they had a daughter together. Unfortunately, the couple divorced in 2013.

Sarah Jessica Parker and Robert Downey Jr.

Sarah Jessica Parker is notoriously private about her marriage to Matthew Broderick but has nothing but nice things to say about her husband. However, before the two actors got together, SJP dated Hollywood’s former bad boy, Robert Downey Jr. The two were pretty serious.

American actress Sarah Jessica Parker, her partner American actor Robert Downey Jr,
Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images

Downey Jr. and SJP dated for seven years before ending their relationship. Downey Jr.’s struggles with addiction put a strain on their relationship, and she couldn’t handle the constant worries. He eventually got sober, but they could have lasted if he had sobered up sooner.

Kim Kardashian and Nick Cannon

Before Kris Humphries, Kanye West, and Pete Davidson came into her life, Kim Kardashian had several other famous boyfriends. The two never confirmed a romantic relationship, but Kardashian and Nick Cannon reportedly dated before she was famous. The two started dating in September 2006.

Kim Kardashian and Nick Cannon
Photo by SGranitz/WireImage

The two only lasted for four months before ending their relationship. Kardashian and Cannon moved on with other people, but if she played her cards right, she could have been one of his many baby mamas. However, she got out before that could happen.

Michelle Rodriguez and Zac Efron

Michelle Rodriguez has dated several famous celebrities, including Cara Delevingne and Zac Efron. She and Efron were an unlikely pair because she was ten years older than him. Rodriguez doesn’t like her relationships to be in the spotlight, which was hard while dating Efron.

Michelle Rodriguez and Zac Efron
Source: Facebook

Efron and Rodriguez only lasted for two months because they were too different to stay together. It was a mutual split, and they had nothing bad to say about each other. It was a short-lived summer fling. Rodriguez moved on with Delevingne a few months later.

Orlando Bloom and Kate Bosworth

Orlando Bloom is one of those actors that is low-key but can make anyone swoon. Some Hollywood starlets have been lucky enough to date the Lord of the Rings star, including Kate Bosworth. He and the beautiful actress started dating in 2003 after meeting on the set of a Gap commercial.

Orlando Bloom and Kate Bosworth
Photo by Niki Nikolova/FilmMagic

Bosworth said, “I knew Orlando before he was famous, so we started dating way back in the day.” They kept their romance quiet, but after a year, Bloom wanted the world to know he was in love with Bosworth. The two later broke up in 2005.

Ben Affleck and Gwyneth Paltrow

In between her engagement to Brad Pitt and her marriage to Chris Martin, Gwyneth Paltrow secretly dated Ben Affleck. The two met in 1997 and dated for two years. Paltrow and Affleck met on the set of Shakespeare in Love.

American actor Ben Affleck and American actress Gwyneth Paltrow
Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images

When they broke up in 1999, the two worked together on a film and briefly rekindled their romance in 2000. However, Affleck “wasn’t in a good place to have a girlfriend.” Paltrow later married Chris Martin, and Affleck moved on with Jennifer Lopez before marrying Jennifer Garner.

Mark Ronson and Rashida Jones

Rashida Jones is famous for starring on Parks and Recreation and The Office, but before she was a big name, she dated Mark Ronson. The music producer became famous for making hits like “Uptown Funk” by Bruno Mars and “Valerie” by Amy Winehouse.

Mark Ronson and Rashida Jones
Photo by Jerritt Clark/Getty Images for TAO Group

Ronson and Jones dated between 2002 and 2004 and were even engaged after a year. Ronson created a crossword puzzle with the message “Will you marry me.” It was sweet and romantic, but they split a year later. It just wasn’t meant to be.

Usher and Rozonda “Chilli” Thomas

In the early 2000s, Usher and Rozonda “Chilli” Thomas were big names in the music industry. People thought of them as a power duo when they started dating in 2001. The two collaborated when Thomas starred in Usher’s music video for “U Got It Bad.”

Usher and
Photo by Frazer Harrison/Getty Images

Unfortunately, Usher and Thomas broke up in 2003 after he cheated on her. Although she was heartbroken, the TLC singer said, “We broke up because I guess it was that time.” She didn’t want to bash him in the press.

Justin Timberlake and Jenna Dewan-Tatum

Both Justin Timberlake and Jenna Dewan-Tatum have had high-profile romances, but everyone forgets that these two dated. They met when she became one of his backup dancers, and he was on the rebound. Timberlake’s relationship with Britney Spears had ended around the same time.

N'Sync (Justin Timberlake) with dancer Jenna Dewan performing
Photo by Frank Micelotta/ImageDirect

Dewan-Tatum played down her relationship with Timberlake by telling Andy Cohen, “We were like friends that then dated. I was not the rebound.” Their relationship didn’t last long, and both moved on with other Hollywood stars. Timberlake married Jessica Biel, and Dewan-Tatum married Channing Tatum.

Brad Pitt and Shalane McCall

Brad Pitt has had high-profile romances with Gwyneth Paltrow, Jennifer Anniston, and Angelina Jolie, but everyone glazes over his relationship with Shalane McCall. He and the former child actress met on the set of Dallas in 1987 when he was 24.

Actress Shalane McCall and actor Brad Pitt
Photo by Getty Images

Pitt landed a four-episode stint on the soap opera when McCall was only 15. Despite their nine-year age gap and her being underaged, the two started dating. Their eyebrow-raising relationship was judged by many, but it didn’t last. They were too far apart in age.

Seal and Tyra Banks

Although Seal’s relationship with Heidi Klum was the talk of the town, he had previously dated one of her close friends. Before Klum, Seal was linked to former America’s Next Top Model host Tyra Banks. Their relationship was brief, but it showed he had a thing for models.

Model Tyra Banks and singer Seal
Photo by Stephane Cardinale/Sygma via Getty Images

The pair had a short romance in 1996 but went their separate ways. Sadly, Banks has not been so lucky in love since their romance nearly 27 years ago. Seal went on to marry Klum in 2005, and they divorced in 2014, while Banks dated Erik Asia for four years.

Scarlett Johansson and Jack Antonoff

Long before Scarlett Johansson was the highest-paid actress in Hollywood and Jack Antonoff became a well-known musician, the two had a sweet high school romance. Johansson and Antonoff were together when they were 17 and attended prom in 2002.

Actress Scarlett Johansson with boyfriend Jack Antonoff
Photo by Evan Agostini/ImageDirect

By the time Johansson was in high school, she had already starred in a few films, and her career was taking off. The two grew apart due to her busy schedule, but there were no hard feelings. Antonoff went on to date Lena Dunham, and Johansson was briefly married to Ryan Reynolds.

Aubrey Plaza and Michael Cera

After meeting on the set of Scott Pilgrim vs. the World, Michael Cera and Aubrey Plaza began dating in 2010. The young actors were deeply in love even though their relationship lasted only a year. The two were young but wanted to take their relationship to the next level.

Actor Jason Schwartzman, actress Ellen Wong
Photo by John Shearer/WireImage

Plaza said, “We drove across the country after we shot that movie and almost got married in Vegas.” She said Cera was the love of her life, and they would always be friends. She has since moved on with Jeff Baena, and the two recently got married in 2021.

Ryan Gosling and Sandra Bullock

We are surprised to see Sandra Bullock on this list twice. She has had some unique romances, and in 2011, she was rumored to be dating Ryan Reynolds. However, that wasn’t the first famous Ryan she dated. A decade prior, Bullock and Ryan Gosling had a year-long romance.

Sandra Bullock, Ryan Gosling
Photo by Sylvain Gaboury/FilmMagic

In 2002, Bullock and Gosling made headlines when they became a couple after meeting on the set of Murder By Numbers. They were big names in the industry, but their 16-year age difference is what really caught the media’s attention.

Madonna and Dennis Rodman

When it comes to eccentric people, Madonna and Dennis Rodman would be at the top of that list. Therefore, their romance was bizarre and surprising for many reasons. Before her marriage to Guy Richie, she and Rodman had a brief fling in 1994.

Madonna and Dennis Rodman
Photo by Getty Images

Shortly after divorcing Annie Bakes, Rodman and Madonna got together. She reportedly offered him $20 million to impregnate her. He didn’t take her up on the offer, which ended their brief two-month relationship. Rodman went on to marry and divorce twice more.

Cameron Diaz and Jared Leto

Since Cameron Diaz retired from acting eight years ago, her life has been fairly private. But there was a time when she was in a high-profile romance with Jared Leto. The two dated between 1999 and 2003, with rumors about an engagement.

Jared Leto & Cameron Diaz
Photo by Jeff Kravitz/FilmMagic

The engagement rumors started when Diaz wore a $15,000 diamond ring to the 2003 Golden Globes. Leto and Diaz never confirmed or denied their engagement, but it didn’t end with wedding bells. She and the actor went broke up and never talked about it again.

Kate Hudson and Alex Rodriguez

Former New York Yankees all-star Alex Rodriguez has been linked to several Hollywood stars like Cameron Diaz, Jennifer Lopez, and Madonna. However, there was a time when the baseball legend dated Kate Hudson. Who would have guessed that she was a Yankees fan?

Alex Rodriguez and actress Kate Hudson kiss
Photo by NYDailyNews/Getty Images

Hudson and Rodriguez had a whirlwind seven-month romance in 2009, just a year after his divorce from Cynthia Scurtis. He and Scurtis were married for six years and had two children together. It seemed that Hudson was just a rebound after his divorce.

Lamar Odom and Taraji P. Henson

The only relationship we associated with Lamar Odom was his marriage to Khloe Kardashian. The two married after only a month of knowing each other and divorced a few years later. While that marriage was a mess, it made all of his other relationships forgetful.

Lamar Odom and Taraji P. Henson
Source: the-sun.com

Before Khloe, Odom was linked to Taraji P. Henson. The two were pictured attending a Golden Globes party in 2009, and it was rumored that he proposed to her. Oddly, this happened just weeks before he proposed to Khloe. Was Odom a serial proposer and cheater?

Wilmer Valderrama and Mandy Moore

The That ‘70s Show star has been linked to Lindsay Lohan and Demi Lovato, but Wilmer Valderrama was linked to Mandy Moore before he dated those ladies. He and Moore dated between 2001 and 2002 while they were still trying to make it in the business.

Wilmer Valderrama and Mandy Moore
Photo by Lester Cohen/WireImage

Their relationship seems like a lifetime ago because Moore and Valderrama have moved on with other people. Moore went on to date Zach Braff in 2004 before settling down with Ryan Adams in 2009. The pair later divorced, and Valderrama got engaged to Amanda Pacheco in 2020.

Tom Cruise and Cher

We would like to “turn back time” to see Tom Cruise and Cher as a couple. The two unlikely lovers briefly dated in 1985, but it didn’t turn into anything more than a fling. Cruise and Cher are a couple no one remembers, but he was apparently in her “top five.”

Tom Cruise & Cher backstage after her performance.
Photo by MCaulfield/WireImage

Cher’s marriage to Sonny Bono in the ‘70s has overshadowed any of her other romances. Additionally, Cruise’s marriages to Nicole Kidman and Katie Holmes were much more publicized because he was a well-known actor when he met those women.

Nick Jonas and Selena Gomez

Back in the day, Nick Jonas was an innocent teenage heartthrob, and Selena Gomez was an adorable Disney Star. It has been hard to keep up with her love life after her on-again-off-again rocky romance with Justin Bieber, but she had other boyfriends before him.

Nick Jonas, Selena Gomez and Joe Jonas
Photo by Rachel Murray/Getty Images for Republic Records

In fact, Gomez and Jonas dated around 2008 when the Jonas Brothers released “Burnin’ Up.” They were just two kids in love, and Gomez appeared in the band’s music video. Although he is married to Priyanka Chopra now, we wish he and Gomez would have lasted.

Alyssa Milano and Justin Timberlake

Considering how many women he dated before Jessica Biel, it’s no surprise that Justin Timberlake is on this list twice. Jenna Dewan-Tatum claimed she wasn’t a rebound after his breakup with Britney Spears, but Alyssa Milano doesn’t deny her rebound status.

Alyssa Milano and Justin Timberlake
Source: gala.de

The two dated in the early 2000s, but Milano didn’t reveal their relationship until years after it ended. She confessed, “Right after Britney broke his heart, I swooped in for the kill.” Milano and Timberlake’s relationship wasn’t serious, but it was surprising. The actress later married David Bugliari.

David Spade and Julie Bowen

We might not understand it, but E! News once described David Spade as “a bachelor-era George Clooney of the comedy world.” He is not a silver fox like Clooney, but he had a string of flings with Hollywood starlets. At the height of his Saturday Night Live success, Spade dated Julie Bowen.

Julie Bowen & David Spade
Photo by Jim Spellman/WireImage

The Modern Family star and Spade were an item in 2002 when Spade starred on Just Shoot Me. Bowen was in Ed at the time, and they were an unlikely duo. However, their relationship was short-lived, like his other flings at the time.

Rosario Dawson and Danny Boyle

About a decade ago, Rosario Dawson and Danny Boyle were spotted out and about looking cozier than friends. The two were rumored to be dating, but the breakup rumors took over just as soon as the dating rumors began. Rosario later spoke about the breakup.

Rosario Dawson and Danny Boyle
Photo by Jared Siskin/Patrick McMullan via Getty Images

Rosario told Net-a-Porter, “It’s not like we announced our relationship, so it’s not like we’re going to announce our breakup.” Regardless of what they said, the pictures were worth a thousand words. They were definitely an item at some point before parting ways.

Jamie Dornan and Keira Knightly

He made a name for himself playing Christian Grey in Fifty Shades of Grey, but before that, Jamie Dornan was just a regular actor. He was still a hunk before starring in the racy film, which is probably why he was able to win over British actress Keira Knightly.

Keira Knightley & Jamie Dornan
Photo by Antony Jones/UK Press via Getty Images

Dornan and Knightly began dating in 2003 after meeting on the set of an ad campaign. The two stunning actors were in a relationship for two years before breaking up in 2005. They kept their romance low-key because no one knew their names at that point.

50 Cent and Chelsea Handler

If you ever wondered what an unlikely pairing looked like, here it is. Back in 2010, talk-show host Chelsea Handler had a brief romance with rapper 50 Cent. Despite telling Oprah that she wouldn’t date somebody “whose name is a number,” Handler dated 50 Cent anyway.

50 Cent and Chelsea Handler
Source: thejasminebrand.com

The rapper, whose stage name is a number, swept the comedian off her feet. Handler and 50 Cent’s romance was short-lived, but she had some interesting things to say about their time together. Handler let everyone know she was “satiated” during their romance.

Seth MacFarlane and Emilia Clarke

Seth MacFarlane is the genius behind Family Guy, and Emilia Clarke famously played Khaleesi in HBO’s Game of Thrones. You would never think their paths would cross, but they somehow found each other in 2012. The unlikely couple only dated for six months before ending things in 2013.

Producer Seth MacFarlane and actress Emilia Clarke
Photo by FilmMagic/FilmMagic

A year after their relationship, Clarke was voted “The Most Desirable Woman in the World” by AskMen readers and Esquire’s “Sexiest Woman Alive” in 2015. It seems MacFarlane missed out, but they weren’t the right match. She went on to date many other Hollywood Hunks, like Charlie McDowell.

Scarlett Johansson and Sean Penn

When Scarlett Johansson was just 26, she started dating 50-year-old Sean Penn. Their 2011 romance made headlines because of their age gap, and many felt the relationship was wrong. Whether it was the age gap, or her blossoming career, Johansson and Penn broke up after five months.

Sean Penn (L) and actress Scarlett Johansson
Photo by Dimitrios Kambouris/VF11/WireImage

Reports swirled that Penn didn’t want to be tied down to Johansson. She was stunning and young, but for some reason, she tried to rekindle their romance. Her attempts were unsuccessful, and it was probably for the best. Johansson did much better without him.

Simon Cowell and Carmen Electra

Simon Cowell is known for being the harsh judge on the X Factor and America’s Got Talent, but not much is known about his past love life. In 2012, he started dating former Playboy model Carmen Electra, but it only lasted about three months.

Simon Cowell, judge and Carmen Electra
Photo by Ray Mickshaw/WireImage for Fox Television Network

Although they broke up, Electra said Cowell was “awesome and very charming.” She might have changed her mind when she discovered that he had not been faithful during their time together. Still, she thought he was “fun,” “smart,” and “really interesting.”

Christina Applegate and Brad Pitt

When Christina Applegate and Brad Pitt showed up together at the 1989 MTV Video Music Awards, everyone assumed they were dating. He was already considered one of the most attractive men in the world, so no one could have blamed Applegate for falling for him.

Brad Pitt & Christina Applegate
Photo by Jeff Kravitz/FilmMagic, Inc

Unfortunately, halfway through the night, Applegate ditched Pitt for another man. Rocker Sebastian Bach insists he was the guy who stole Applegate from Pitt, but she has never confirmed this. This is probably the shortest relationship on the list because it only lasted a few hours.

Jake Gyllenhaal and Kirsten Dunst

After starring in Spiderman in 2002, Kirsten Dunst shot to fame and became the “It Girl” of the moment. Many Hollywood actors had their sights set on her, including Jake Gyllenhaal. He was lucky enough to woo her, and they began dating in 2002.

Kirsten Dunst and Jake Gyllenhaal
Photo by Jon Kopaloff/FilmMagic

After two years together, Gyllenhaal and Dunst went their separate ways. It was a heartbreaking time because fans were rooting for them. In 2009, Dunst said, “It would be nice to see him, but we’re not good friends.” They could have made a cute family.

Ashton Kutcher and January Jones

Ashton Kutcher is better known for his marriages to Demi Moore and Mila Kunis. However, he had a love life before those two ladies. In 1998, Kutcher and blonde bombshell January Jones were an item. The two appeared on red carpets together and looked loved up.

Ashton Kutcher and January Jones during
Photo by J. Vespa/WireImage

Although they seemed happy, Kutcher and Jones broke up in 2001. It didn’t take long for her to move on, and she started dating Josh Groban two years later. That relationship didn’t last, and Jones never got married. Meanwhile, Kutcher is now happily married to Kunis.

Sheryl Crow and Owen Wilson

In 1999, before she was famously engaged to Lance Armstrong, Sheryl Crow dated Owen Wilson. The goofy actor and Crow dated for two years before calling it quits in 2001. Wilson and Crow had a sweet relationship, but she said it didn’t last for a specific reason.

Owen Wilson and Cheryl Crow attend the world premiere of
Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images

Crow revealed, “I have always gone out with guys who were highly successful, which would seem like it would put me at an equal level. But what ends up happening is that one of you becomes smaller – and it was always me.”

Jessica Biel and Chris Evans

Jessica Biel is now married to Justin Timberlake, but there was a time when she dated Captain America. Before her marriage, she had many high-profile romances, including the one with Chris Evans. The two started dating during her final years on 7th Heaven.

Jessica Biel & Chris Evans at PlayStation 2 Anniversary Party in Los Angeles
Photo by Gregg DeGuire/WireImage

Biel and Evans began their relationship in 2001 and surprisingly dated on and off until 2006. During the fallout from her relationship with Evans, Biel met Timberlake. While Biel and Timberlake are adorable, we would love to see what she and Evans’ children would have looked like.