1. Carrie Fisher & Dan Aykroyd
Carrie Fisher and Dan Aykroyd’s romance was as unexpected as it was brief. The two met while filming The Blues Brothers in 1980 and quickly hit it off. Dan even proposed in the middle of a choking incident—he saved her life with the Heimlich maneuver and then popped the question. Though she said yes, their engagement didn’t last long. Carrie later said she felt more like his wife than his fiancée, but ultimately, she reunited with her on-again, off-again love, Paul Simon shares WBBH.
Dan, for his part, recalled their time together fondly and joked that he would have been a good husband because he loved to clean. While they may not have been meant to be, their short-lived engagement is a fun piece of Hollywood history. It’s hard to imagine Princess Leia and one of the Ghostbusters tying the knot, but for a brief moment, it almost happened.
2. Cher & Gene Simmons
Cher has been linked to plenty of famous faces, but one of her most surprising romances was with Gene Simmons. The KISS bassist and the pop icon dated in the late ’70s, and Cher even called him one of her greatest loves. Their relationship was unusual, as Gene wasn’t known for his monogamy, but Cher didn’t seem to mind. She even introduced him to her kids, and he got along well with them explains PEOPLE.
However, their love story ended when Gene moved on with another music icon—Diana Ross shares ReMIND Magazine. He later admitted that Cher was the one who set them up, thinking they’d hit it off. That must have stung a little, but Cher handled it with grace. Looking back, it’s wild to think that the “I Got You Babe” singer and the KISS rocker were once an item.
3. Madonna & Sean Penn
Madonna and Sean Penn’s marriage was as passionate as it was volatile. They tied the knot in 1985 on her birthday, with helicopters full of paparazzi hovering overhead. From the start, their relationship was a whirlwind of love and chaos. They fought just as fiercely as they loved, and their union was plagued by tabloid headlines and public outbursts says Yahoo.
By 1989, they had called it quits, with Madonna filing for divorce. There were allegations of domestic issues, though both have remained tight-lipped about the details over the years. Despite their turbulent past, they’ve been spotted together on occasion and seem to have buried the hatchet. It’s hard to believe they were once Hollywood’s most talked-about couple, but for a few years, they were.
4. Sally Field & Burt Reynolds
Sally Field and Burt Reynolds had one of the most talked-about relationships of the late ’70s and early ’80s. They met while filming Smokey and the Bandit in 1977, and their chemistry was undeniable. Off-screen, their relationship was just as intense, lasting nearly five years. Burt often called Sally the love of his life, but their relationship wasn’t always smooth sailing.
Sally later admitted that she felt overwhelmed by Burt’s larger-than-life personality and the pressure he put on their romance. When they finally split in 1982, it was heartbreaking for both of them. Years later, Burt expressed regret over how things ended, but Sally had already moved on. It was a classic case of love that burned bright but couldn’t last.
5. Farrah Fawcett & Ryan O’Neal
Farrah Fawcett and Ryan O’Neal had a love story that spanned decades, but their early years together were full of drama. They first got together in the late ’70s, while Farrah was still riding high on her Charlie’s Angels fame. Their relationship was passionate but rocky, with breakups and reconciliations sprinkled throughout. Though they never married, they had a son together, Redmond, in 1985.
Even when they split in the ’90s, they never truly let go of each other. When Farrah was diagnosed with cancer in the 2000s, Ryan was by her side until her final days. Their love story wasn’t perfect, but it was enduring. It’s hard to forget the image of them together, even if their romance was anything but smooth.
6. Marie Osmond & Andy Gibb
Marie Osmond and Andy Gibb’s relationship was short-lived but left a lasting impression on fans. The teen idols were both at the height of their fame in the late ’70s when they started dating. They were picture-perfect together, but behind the scenes, things weren’t so ideal. Andy was struggling with substance issues, and Marie wasn’t ready for a serious commitment.
Marie later admitted that Andy was charming and sweet, but his personal demons made a relationship difficult. They remained friends, even after breaking up, but Andy’s struggles continued. Sadly, he passed away in 1988 at just 30 years old. Looking back, their romance feels like a fleeting moment of youthful love that was never meant to last.
7. Jane Fonda & Donald Sutherland
Jane Fonda and Donald Sutherland’s romance began in the early ’70s, during the making of Klute. Their chemistry was electric both on and off the screen. Beyond their love affair, they were politically active together, speaking out against the Vietnam War. They seemed like the ultimate power couple—smart, passionate, and unafraid to shake things up.
But by 1972, their relationship had run its course. Jane later moved on to a string of high-profile marriages, while Donald continued his impressive acting career. Though their time together was brief, it was undeniably impactful. They weren’t just lovers; they were partners in activism, which made their breakup all the more surprising.
8. Goldie Hawn & Bruno Wintzell
Before Goldie Hawn settled into her longtime relationship with Kurt Russell, she was involved with Swedish singer Bruno Wintzell. Their romance in the mid-’70s was a whirlwind, though it didn’t last long. Goldie was fresh off her divorce from Gus Trikonis and still figuring out what she wanted.
Bruno was charming, but their relationship faded quickly, and Goldie eventually moved on. Few people remember this brief love affair because it was overshadowed by her later relationships. Still, for a moment in time, Goldie and Bruno were an item. It’s a fun little footnote in her romantic history.
9. Barbra Streisand & Don Johnson
Barbra Streisand and Don Johnson’s romance in the late ’80s was unexpected, to say the least. The Broadway diva and the Miami Vice star seemed like an odd pairing, but they had undeniable chemistry. They even recorded a duet together, “Till I Loved You.”
Their relationship didn’t last long, but it certainly got people talking. Barbra was known for dating high-profile men, but Don was a bit of a wild card. After their split, they both moved on—Don rekindled things with Melanie Griffith, while Barbra later married James Brolin. Still, their brief romance remains a fascinating Hollywood tidbit.
10. Susan Dey & David Cassidy
Fans of The Partridge Family loved the idea of Laurie and Keith Partridge together in real life. Susan Dey certainly had a major crush on David Cassidy while they were filming the show in the early ’70s. However, David didn’t reciprocate her feelings at first, which left Susan heartbroken. They eventually did date for a short time after the show ended, but it didn’t work out.
David later admitted in his autobiography that he regretted how he treated Susan. He said he never took their relationship seriously, even though she genuinely cared for him. Susan, on the other hand, was reportedly so hurt by their breakup that she refused to attend the Partridge Family reunion years later. It’s a bittersweet love story that many fans didn’t even realize happened.
11. Cybill Shepherd & Peter Bogdanovich
Cybill Shepherd and director Peter Bogdanovich had a romance that was straight out of a Hollywood movie. He cast her in The Last Picture Show in 1971, and they fell for each other almost immediately. Their relationship was intense, but it wasn’t easy—Peter was married at the time, and their affair made headlines. Eventually, he left his wife, and he and Cybill became a full-fledged couple.
However, their love story didn’t last. The pressures of Hollywood and their own personal struggles pulled them apart. Cybill moved on to other relationships, while Peter continued his career in filmmaking. They remained friends over the years, but their romance is one that many people have forgotten.
12. Tatum O’Neal & John McEnroe
Tatum O’Neal and John McEnroe were an unlikely pairing, but their romance in the ’80s was serious. They got married in 1986 and had three children together. Both were young, successful, and a little rebellious, which made for a fiery relationship. But their marriage was filled with ups and downs, and their arguments often made headlines.
By 1994, they had divorced, and things turned bitter between them. John later claimed that Tatum’s struggles with substance issues contributed to their split, while she accused him of being controlling. They eventually found a way to co-parent their children, but their relationship never fully recovered. It was a love story that started with passion but ended in heartbreak.
13. Diane Keaton & Warren Beatty
Diane Keaton and Warren Beatty had a brief but intense relationship in the late ’70s. They met while working on Reds, a film Warren directed and starred in. Their romance blossomed quickly, and Diane was completely smitten. However, Warren’s reputation as a Hollywood ladies’ man made things complicated.
Diane later said she adored Warren but knew he wasn’t the settling-down type. Their relationship fizzled out, but they remained friends over the years. She even joked that he was one of the most fascinating men she had ever dated. While it didn’t last, their time together was certainly memorable.
14. Brooke Shields & Dean Cain
Before Dean Cain became Superman on Lois & Clark, he was in a serious relationship with Brooke Shields. The two dated while they were students at Princeton in the early ’80s. Brooke later admitted that she was deeply in love with Dean, but she struggled with intimacy due to her strict upbringing. She revealed in her memoir that he was incredibly patient with her, but it eventually put a strain on their relationship.
After college, they went their separate ways, with Dean pursuing acting and Brooke continuing her modeling and film career. Despite their breakup, Brooke has only spoken positively about their time together. She even called him a “beautiful person” who treated her with kindness. It was a college romance that could have been something more, but life took them in different directions.
15. Linda Ronstadt & Jerry Brown
In the late ’70s, Linda Ronstadt and California Governor Jerry Brown were one of the most talked-about couples in the country. The rock singer and the politician seemed like an odd match, but they made it work for a few years. Linda was at the peak of her music career, while Jerry was making waves in politics. Their relationship was often in the spotlight, with rumors even suggesting she might become the First Lady one day.
However, Linda wasn’t interested in the political lifestyle, and they eventually drifted apart. She later said she had no regrets about their relationship, and they remained friends long after their split. Jerry went on to serve multiple terms as governor, while Linda continued making music. It was a unique pairing that had people buzzing at the time but has since faded into history.