MomSkoop
Hollywood romances are often short-lived, and some fade from memory faster than others. Over the years, A-list celebrities have dated each other in surprising combinations that now seem almost unbelievable.
Many of these relationships happened before social media made every celebrity move public knowledge. Get ready to take a trip down memory lane and rediscover some of the most forgotten celebrity pairings that once made headlines.
1. Jennifer Aniston & Vince Vaughn
After one of Hollywood’s most publicized divorces from Brad Pitt, Jennifer Aniston found comfort with an unexpected co-star.
She and Vince Vaughn met while filming The Break-Up in 2005, and their on-screen chemistry quickly translated into real life.
The relationship offered Aniston a much-needed distraction during a difficult time.
Paparazzi followed them everywhere, capturing their dates and getaways throughout 2006.
Despite appearing happy together, the romance fizzled out by the end of that year.
Vaughn later married a real estate agent, while Aniston continued her journey through Hollywood relationships.
Their brief time together now feels like a minor footnote in both of their romantic histories.
2. Ryan Reynolds & Alanis Morissette
Long before Blake Lively and his Deadpool fame, Ryan Reynolds had a completely different life partner in mind.
He was actually engaged to the Grammy-winning Canadian singer Alanis Morissette during the mid-2000s.
Their relationship lasted several years, and they seemed quite serious about their future together.
When things ended in 2007, Morissette channeled her heartbreak into music.
Her album Flavors of Entanglement became a therapeutic outlet for processing the breakup.
Reynolds moved on to marry Scarlett Johansson shortly after, while Morissette eventually found happiness with rapper Souleye.
Most fans today associate Reynolds only with Lively, making this earlier engagement a true forgotten chapter.
3. Justin Timberlake & Cameron Diaz
Picture this: a former boy band heartthrob dating one of Hollywood’s most beloved comedic actresses.
Justin Timberlake and Cameron Diaz made quite the power couple during their nearly four-year relationship in the early 2000s.
They attended award shows together and seemed genuinely smitten with each other at every public appearance.
Their relationship spanned from 2003 to 2007, a period when both were at career peaks. Timberlake was transitioning from *NSYNC to solo superstardom, while Diaz was ruling the box office.
After their split, Timberlake eventually married Jessica Biel, and Diaz later wed rocker Benji Madden.
Today, most people forget these two ever shared red carpets and romantic vacations together.
4. Bradley Cooper & Renée Zellweger
Before Bradley Cooper became People’s Sexiest Man Alive, he dated an Oscar-winning actress most people completely forgot about.
Cooper and Renée Zellweger met on the set of the horror film Case 39 and began dating around 2009.
Their relationship lasted approximately two years, during which they kept things relatively private.
They did make appearances together at various award shows and industry events.
Both seemed happy, but the relationship ended amicably in 2011 without much public drama.
Zellweger later stepped back from the spotlight for several years, while Cooper’s career skyrocketed with films like Silver Linings Playbook and A Star Is Born.
Their romance now seems like ancient history to most fans.
5. Madonna & Tupac Shakur
This pairing sounds almost too wild to be true, yet it absolutely happened.
Madonna and Tupac Shakur had a secret relationship in the early 1990s that only became widely known years later.
Tupac revealed details in a prison letter to Madonna, which was later auctioned and made public.
According to Tupac’s letter, he ended things because he worried about how their interracial relationship would affect his image and career.
Madonna confirmed the relationship in interviews years after his tragic death.
Their romance represents one of pop culture’s most unexpected crossovers between the music worlds of pop and hip-hop.
Had social media existed then, this relationship would have broken the internet daily.
6. Ashton Kutcher & January Jones
Way back before either became household names, these two struggling actors dated in Hollywood.
Ashton Kutcher and January Jones were together in the late 1990s when both were trying to break into the entertainment industry.
They were young, broke, and chasing their dreams together in Los Angeles.
The relationship ended before Kutcher landed his breakthrough role on That ’70s Show.
Jones later found fame as Betty Draper on Mad Men, becoming a television icon.
In later interviews, Jones has been less than flattering about their time together, suggesting Kutcher wasn’t particularly supportive.
Meanwhile, Kutcher went on to date and marry several famous women, making this early relationship easy to overlook.
7. Rihanna & Leonardo DiCaprio
Did these two actually date, or were they just really good friends who partied together?
Rihanna and Leonardo DiCaprio were spotted together multiple times throughout 2015, sparking intense dating rumors.
They were photographed leaving the same clubs, attending the same parties, and looking very cozy.
Neither star ever officially confirmed a romantic relationship, keeping fans guessing the entire time.
DiCaprio is famously private about his personal life, while Rihanna enjoys keeping people on their toes.
The speculation eventually died down, and both moved on without ever addressing what really happened between them.
Whether it was romance or friendship, their connection remains one of Hollywood’s most intriguing mysteries from that year.
8. Scarlett Johansson & Jared Leto
In the early 2000s, two rising stars briefly connected in a relationship that barely registered on the public radar.
Scarlett Johansson and Jared Leto dated for a short period when both were establishing themselves as serious actors.
They managed to keep things extremely low-key despite their growing fame.
The relationship happened before Johansson became a Marvel superhero and before Leto won his Oscar.
Both were young, attractive, and talented, making them a natural pairing at the time.
Their romance ended quietly without any public drama or tabloid coverage.
Today, with both having had numerous other high-profile relationships, this brief coupling has been completely overshadowed and forgotten by most entertainment fans.
9. Ben Affleck & Gwyneth Paltrow
Before Bennifer became a cultural phenomenon, Ben Affleck had another high-profile Hollywood romance.
He dated Gwyneth Paltrow seriously in the late 1990s, during the height of her Shakespeare in Love success.
They were both young, beautiful, and on the verge of major stardom.
Paltrow has spoken about the relationship in interviews over the years, describing Affleck as her first real love.
She’s also mentioned that the relationship was intense and sometimes complicated.
After they split in 2000, Affleck went on to his famous relationship with Jennifer Lopez, while Paltrow married Coldplay’s Chris Martin.
Their late-90s romance now feels like it happened in a completely different Hollywood era.
10. Katy Perry & Russell Brand
Some marriages burn bright and fast, and this one definitely fits that description.
Katy Perry and British comedian Russell Brand had a whirlwind romance that led to marriage in late 2010.
Their wedding was an elaborate ceremony in India, complete with elephants and traditional celebrations.
Just fourteen months later, Brand filed for divorce, citing irreconcilable differences.
The split shocked fans who thought the quirky couple was perfect together.
Perry later revealed in interviews that their different lifestyles and career demands made the marriage unsustainable.
Brand wanted a quieter life, while Perry was at the peak of her pop stardom.
Their brief union now seems like a fever dream that many fans have completely forgotten about.
11. Sarah Jessica Parker & Robert Downey Jr.
Long before Carrie Bradshaw and Iron Man, these two actors shared a significant relationship.
Sarah Jessica Parker and Robert Downey Jr. dated for nearly seven years in the late 1980s and early 1990s.
They lived together and were quite serious about their future.
Unfortunately, the relationship coincided with Downey’s most severe struggles with substance abuse.
Parker later described the emotional toll of loving someone battling addiction.
They eventually split in 1991, with Parker moving on to marry Matthew Broderick.
Downey overcame his demons, became one of Hollywood’s highest-paid actors, and married producer Susan Downey.
Their lengthy relationship is now a distant memory for most fans of either star.
12. Mila Kunis & Macaulay Culkin
For nearly a decade, Mila Kunis was in a serious relationship with a former child star.
She and Macaulay Culkin dated from 2002 to 2011, making it one of Hollywood’s longest relationships.
Despite its duration, they managed to keep things remarkably private.
Culkin had stepped away from acting after his childhood fame, while Kunis was building her career beyond That ’70s Show.
They seemed to provide each other with stability away from the Hollywood spotlight.
After their split, Kunis reconnected with former co-star Ashton Kutcher, whom she eventually married.
The Culkin chapter of her life now seems almost unbelievable to fans who only know her with Kutcher.
13. Nicole Kidman & Lenny Kravitz
Here’s a surprising fact: Nicole Kidman was once engaged to rock legend Lenny Kravitz.
This happened in the early 2000s, shortly after Kidman’s divorce from Tom Cruise.
The engagement remained secret at the time and only became public knowledge years later when Kidman casually mentioned it.
Kravitz and Kidman reportedly connected over their shared experiences with high-profile divorces and the pressures of fame.
Their relationship was serious enough for an engagement ring.
The engagement ended quietly before any wedding plans materialized.
Kidman went on to marry country singer Keith Urban, while Kravitz remained famously single.
Most fans had no idea this engagement even existed until Kidman revealed it in a later interview.
14. Drew Barrymore & Tom Green
Drew Barrymore’s romantic history includes one particularly quirky and short-lived marriage.
She married comedian Tom Green in 2001 after they met during the filming of Charlie’s Angels.
Their relationship was playful and unconventional, matching both of their eccentric personalities.
Unfortunately, the marriage lasted less than a year before ending in divorce in 2002.
The split was relatively amicable, with both citing the usual irreconcilable differences.
Green later battled testicular cancer, which added strain to their already struggling marriage.
Barrymore has since been married twice more and is now focused on her talk show and business ventures.
This brief marriage to Green feels like a distant, almost forgotten blip in her colorful romantic history.