Diane Lane has had her share of romantic trials, but one in particular continues to follow her.

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Academy Award-nominated actress Diane Lane has been a Hollywood fixture since the age of 14. However, while her career has undoubtedly thrived, her romantic life has often been in a state of turbulence. And there’s one relationship in particular that appears to have caused her more pain and public attention than any other.

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That’s right, the star dated Josh Brolin – a fellow A-lister who’d popped in and out of Lane’s professional circle throughout the years. The couple first got together in 2002, after they’d ran into each other at a party. By the following year they were engaged, and within another year or so they’d become husband and wife. But it seems that even from the start, all was not well between the couple, and the extent of their troubles would ultimately reach the public eye.

Yes, despite the fact that Lane and Brolin stayed married for nine years and that their split was supposedly amicable, one troubling incident in 2004 left Lane with no choice other than to call the cops. And since then, Brolin has voiced his fair share of comments about what really went on that night, and Lane, too, has made a particularly poignant confession when it comes to her rocky love life.

Lane, you see, had exposure to difficult marriages from a very young age. Just 13 days after she’d been born, her acting instructor father split with her Playboy centerfold mother. And the future star therefore spent her first six years with her mom in Mexico, before her dad gained custody. Then, when Lane turned 15, her life suddenly got even more complex.

In 1980 Lane decided she wanted to spread her wings, and so she fled to Los Angeles with her actor pal Christopher Atkins. On her return to New York, she moved in with the family of another friend. But soon after this she was seized by her mother and taken to Georgia. After managing to break free from her mom’s clutches after just six weeks, however, she headed back to New York – refusing to talk to the Playboy star for three years.

Of course, Lane was already an experienced actress by this point. Inspired by her Pentecostal preacher grandma’s theatrical sermons, she took to the stage aged just six. And as she entered her teens, she appeared in A Little Romance alongside Laurence Olivier. The acting great was seemingly impressed by Lane’s performance, even going so far as to hail her as the “new Grace Kelly.”

Unlike many child stars, then, Lane made the shift to adult success look effortless. She earned rave reviews for her performances in Rumble Fish and The Outsiders, both of which featured a Brat Pack cast. However, Lane’s career took a blow when she turned down box office successes Risky Business and Splash to appear in flops such as The Cotton Club and Streets of Fire.

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Lane subsequently took a break from the film industry to rebuild a connection with her mother – something that was very important to the star. But she eventually returned to the fold with roles in Lady Beware and The Big Town. Then, in 1989 she delivered an Emmy-nominated performance in popular drama series Lonesome Dove. And after narrowly missing out on the lead role in Pretty Woman, Lane added to her filmography with parts in Chaplin and My New Gun.

Lane remained a regular face on the big screen throughout the 1990s thanks to films such as Judge Dredd and Jack. But she ultimately struggled to find a movie worthy of her talents. That is, until she appeared alongside Anna Paquin and Viggo Mortensen in 1999’s A Walk on the Moon. And after showing up in disaster movie A Perfect Storm, Lane landed the role of her career.

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That’s right, in 2002 Lane starred as an adulterous housewife in the drama Unfaithful. And her performance was recognized with nominations at both the Golden Globes and the Oscars. Owen Glieberman of Entertainment Weekly described Lane as a revelation, adding, “The play of lust, romance, degradation and guilt on her face is the movie’s real story.”

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Lane then picked up a second Golden Globe nod for her leading role in 2004’s Under the Tuscan Sun. And following parts in Must Love Dogs, Fierce People and Hollywoodland, she teamed up with Richard Gere again on 2008’s Nights in Rodanthe. Her prolific streak then continued with key roles in action-adventure Jumper and horror Untraceable.

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After publicly expressing her worries about becoming typecast, Lane starred in Disney movie Secretaria. She then received yet more awards recognition for her turn in the HBO film Cinema Verite. Lane subsequently went on to play Superman’s mother in Man of Steel, lend her voice to Pixar’s smash Inside Out and appear alongside Helen Mirren and Bryan Cranston in Trumbo.

Lane returned to the stage for the first time since 1989 in a production of Tennessee Williams’ Sweet Bird of Youth. In 2018 she appeared on the small screen in Amazon drama The Romanoffs and in House of Cards’ final season. A year later she played a love interest of Matthew McConaughey in the much-maligned Serenity.

And Lane shows no signs of slowing down, either. She will reportedly reunite with her Wild Bill co-star Jeff Bridges in an as-yet-unnamed movie directed by Reed Morano. Lane is also set to appear in the thriller Let Him Go opposite Kevin Costner. And she’ll return to television with a role in FX’s comic book adaptation Y: The Last Man. Now, with all of these acting stints to her name, you may be wondering how Lane has ever had the time to hold down a relationship. She does seem to have had quite a few, though – yet they haven’t all been rosy.

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Lane’s first fling was with fellow actor Chris Lambert, whom she met during a promotional trip to Paris for The Cotton Club in 1984. The pair enjoyed a brief dalliance before going their separate ways. But two years later they found themselves sharing the screen together in Priceless Beauty. And this time things got a lot more serious.

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In 1988 Lane and Lambert walked down the aisle together at a ceremony in the New Mexico city of Santa Fe. And five years later they welcomed their first and only child into the world – a girl named Eleanor. Sadly, things went awry soon after, and by 1995 the once-happy couple had officially divorced.

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After this, Lane was regularly spotted with her one-time co-star Richard Gere. In the early ’00s, however, she forged a romantic relationship with another A-lister, Josh Brolin. Ironically, the pair had first crossed paths when Brolin starred alongside Lane’s first husband Lambert on The Road Killers. But they only struck up a connection nearly a decade later.

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Recalling the two meetings during a 2005 interview with People, Lane said, “It was like ‘Hello’ at the craft-service table. Flash forward nine years and we met at this restaurant after a premiere. He was like, ‘Hi. Remember me?’ We started talking about our kids, because it turned out that he had a daughter who was the same age as my daughter. Now they go to school together.”

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Brolin, though, had previously been engaged to another actress, Minnie Driver. But in 2003 he added Lane to his list of fiancees, having popped the question on the Fourth of July. The pair said ‘I do’ at the 97-acre Los Angeles ranch owned by Brolin in front of several other famous faces. These included the likes of Barbra Streisand and James Brolin – the groom’s stepmother and father – and Lane’s maid of honor, Elizabeth Perkins.

As a result, Lane also became a stepmother herself to Brolin’s children Eden and Trevor. And in a 2008 interview with Redbook, the actress admitted that her parenting style differs from her husband’s. She said, “Sometimes I’m grateful when he’s strict with my daughter. Sometimes I’m like, ‘Ooh. Wow. I bet she’s gonna come talk to me later and be like… [her lower lip quivers].’”

Lane was also happy to discuss her relationship with Brolin in a 2010 interview with Ladies’ Home Journal. She told the magazine, “At my own peril I will quote Mae West, who said, ‘Getting married is like trading in the adoration of many for the sarcasm of one.’ I embrace that. Bring it on. Because that’s what intimacy is.”

“It’s a willingness to be vulnerable, a willingness to bite my tongue and a willingness to set an example of what I believe in,” Lane continued. “And it’s hard. But worth it. I recently said to Josh, ‘Being in a relationship makes it impossible to avoid yourself.’ It may not always make me comfortable, but it sure has made me a better person. And I’ll take that any day.”

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But tongues started wagging at the end of 2012 when a visibly upset Lane was pictured ignoring Brolin as she walked away from a West Hollywood restaurant. A few months later, a spokesperson verified that the pair had gone their separate ways. According to Us Weekly, however, the split had in fact been amicable and there hadn’t been a villain of the piece.

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Soon after, Lane was grappling with being a single woman again. And in a candid chat with More magazine in 2016, the actress admitted that “relationships with the opposite sex are the most challenging things I’ve done.” She went on to add, “You lose your compass, gravity changes, you don’t know what’s up or down, you’re trying to figure it out. You’re trying to make everybody happy, including yourself, and it’s just… it’s humbled me.”

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Lane then listed the benefits of living a single life. She said, “Every room [in my house] is my room. I’ve been traveling more this year than I ever have, because I can. Suddenly filming a movie in South Africa is no biggie. Sure, I’d like a relationship again, but I’m loving the solitude as well.”

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Unlike most of her Hollywood peers, Lane claimed that she’s not too concerned about getting older, either. She told More, “I rehearsed 50. I kind of stared at it a long time. I wasn’t going to let it terrify me. My relationship with aging is cozy. I’m not trying to play 29 and holding on with white knuckles, you know? I’m done saying, ‘I’m sorry I wasn’t who you needed or wanted me to be’ to everybody in my life.”

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But Lane did admit that she has plenty of insecurities, many of which were brought on by the beauty industry. She complained to More, “Remember those ‘Don’t hate me because I’m beautiful’ ads? We grew up with that s***. It was the start of that psychoanalytical thing in our culture where we market to women by making women compete with each other. I found it very discordant.”

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As a result, Lane confessed that she has just as many body issues as the next woman. She added, “The largest room in the world is room for improvement. You know, some mornings my thighs are fat. Some days my hair looks great. That’s the human condition. Things hurt me just as much as anyone else. My insecurities, failures. I’m vulnerable to comparisons.”

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Of course, there’s still one particular part of Lane’s married life that has followed the star around since it occurred. In 2004 the actress reportedly called the police, alleging that she had been physically struck by her then-husband. Brolin was subsequently arrested and charged with the offense of spousal battery.

However, things took a confusing turn when Lane reportedly didn’t want Brolin to be arrested or to press any charges. Speaking to the New York Daily News, a spokesperson for the pair claimed, “There was a misunderstanding at their home… [The arrest was] for the lowest-end misdemeanor charge of domestic battery.”

The spokesperson continued, “In cases involving the possibility of any physical contact, the police have to arrest first, ask questions later.” Brolin was allowed to return home after being bailed out. And the pair were reportedly “embarrassed the matter went this far.” But inevitably, rumors about just what exactly happened on that day continued to persist.

Lane has never spoken publicly about the incident. However, in 2010 Brolin decided to address the issue head on in a candid interview with Playboy magazine. Referring to his arrest, Brolin said, “I feel rage about that. I feel I’ve gotten to a point where I can’t explain it, defend it or compensate for it. I can’t say, ‘No, I’m actually a really good guy and that didn’t happen.’”

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An increasingly emotional Brolin continued to protest his relative innocence, adding, “Everybody knows what happened because it’s all out there. I talked big, she said ‘F*** you’ and called the cops, and somebody had to go to jail. This will be there for the rest of my life. That f***ing sucks. It’s been so disruptive to our lives.”

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“It’s also post-O.J., and that horrifies us both,” Brolin then added. “It kills me, man. It kills me.” The actor also firmly stated that he would never cheat on Lane. “I don’t f*** around on my wife. I mean, check her out, man. My relationship with my wife is fantastic.”

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Brolin then remained relatively quiet about the incident. That is, until it was brought up in a 2018 interview with the New York Times. He said, “God, I’ve never been so careful with my words. Ever. Maybe in all 50 years. And there’s no reason for me to be other than there’s no explaining it. Do you know what I mean?”

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“The only person who can explain that would be Diane, and she’s chosen not to,” Brolin continued. “So I’m okay with that.” The actor also acknowledged that he’d previously attempted to offer an explanation for Lane’s call to the police. However, he now understands that it’s perhaps best if he says nothing at all.

“I was more reactive, I was more, ‘People need to know the truth,’” admitted Brolin. “Whatever I say is going to sound like compensation for a perpetrator. I’ve gotten to a place where all that matters is that I have control over my behavior, and at that time, it was a little more chaotic.”

Brolin wasted little time in moving on from Lane. You see, just two years after divorcing the actress he got engaged to his ex-assistant Kathryn Boyd. The pair tied the knot a year later and in May 2018 revealed that they were expecting a baby. Westlyn Reign Brolin was born six months later.

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Lane, on the other hand, hasn’t been publicly linked with anyone since the divorce. But in 2019 her Serenity co-star Matthew McConaughey revealed that she’s been his celebrity crush since the late 1980s. The Oscar winner told Entertainment Tonight that he became enamored with Lane after watching her in Lonesome Dove. He said, “So then I get to work with her. She looks about the same as she did back then, and she’s one of our great actresses.”

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A slightly flustered Lane revealed that she initially didn’t know how to take the news. She told Entertainment Tonight, “I couldn’t cope. I said, ‘Thank you for the compliment. I’m dying, and… love you too babe.’” Lane also expressed hope that she’d lived up to McConaughey’s picture-perfect idea of her.

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Yet Lane has not been the only celebrity to open up about her love life. “The Way of Love,” “Don’t Hide Your Love,” “Love and Understanding.” Cher has sung about The Big L throughout her glittering and enduring career. And as Cher has a list of ex-husbands and ex-boyfriends as long as her discography, it’s a subject that she seemingly knows all about. But in 2018 the legendary diva revealed the fascinating story behind perhaps her unlikeliest conquest.

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So Cher’s eventful love life evidently began in her mid-teens when she left high school for the bright lights of Los Angeles. The youngster then began performing on stage with Sonny Bono – a singer 11 years her senior – whom Cher admits she was instantly smitten with. In 2010 she told Parade magazine, “I swear to God, the moment I saw Sonny, everyone else in the room disappeared. He was the coolest guy.”

Sonny didn’t exactly feel the same way, though; the singer apparently told Cher that he wasn’t attracted to her at all in their early stages. But that all changed when the pair enjoyed a movie night in which he leaned in for a kiss. And the talented couple obviously made their professional relationship a highly personal one when they walked down the aisle together in 1964. Five years later, they welcomed son Chaz into the world as well.

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Sadly, though, the Sonny-and-Cher love story didn’t get a happy ending. The pair in fact went their separate ways in 1974 – and at times their divorce got pretty ugly. But the former spouses eventually managed to rebuild their friendship, and Cher even helped Sonny with his successful mayoral campaign in Palm Springs. Tragically, however, Sonny lost his life while skiing in early 1998.

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Back in the early 1970s, Cher wasted little time in moving on from Sonny. In fact, she was still going through divorce proceedings when she began dating David Geffen. The pair had first met the previous decade when Cher had collaborated with another successful record producer: Phil Spector. Geffen also helped the star with the negotiation side of her messy split from Sonny Bono.

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In the early 1990s, though, Geffen revealed that he was gay. But Cher insists that her relationship with the producer was entirely genuine. “I was the first person to share his bed and to share his life,” the star is quoted as saying in The Operator, a Geffen biography published in 2001. “People don’t believe that, or they don’t want to believe it, or they don’t understand how it could be. But we were really crazy about each other.”

But the pair’s plans for marriage were apparently derailed when Cher fell in love with another music industry name. This time around, then, it was Gregg Allman who became the object of her affections after the pair met at one of the rock star’s shows. And within just five days of her divorce from Sonny Bono being concluded, Cher said “I do” to Allman at a ceremony in Las Vegas.

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Yet the ink on that marriage certificate was still drying when Cher decided to file for divorce. Yes, just nine days after walking down the aisle, the singer allegedly felt that she could no longer put up with her new husband’s substance abuse problems. But the pair briefly managed to get things back on track, and in 1976 Cher gave birth to their son, Elijah Blue.

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The couple even ventured into the studio together to record the duets collection Two the Hard Way. But the album failed to connect with audiences, and shortly after Cher and Allman also realized that they were better off apart. And perhaps unsurprisingly, Cher once again moved on with another musician soon after.

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In 1979, in fact, Cher settled down with one of the rock scene’s wildest names: Gene Simmons. But their relationship wasn’t a particularly conventional one. In 1979, for instance, Cher told People, “I’m going through a very liberated phase right now. I think I have a very masculine attitude to dating. Gene might spend time with another woman and stay the night, but he wants her to leave in the morning, so he can get on with his day.”

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Unfortunately for Cher, Simmons seemingly took advantage of her relaxed attitude to dating. In fact, after Cher informed Simmons that her friend Diana Ross was the ideal person to give advice about possible Christmas presents, the rocker and the Motown legend went shopping together. But Simmons evidently got more than he bargained for, and shortly after he dumped Cher for her BFF.

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But Cher didn’t spend much time crying over this betrayal. In 1980, in fact, she began stepping out with Les Dudek – a session guitarist six years her junior – who also performed in her short-lived backing band, Black Rose. In 1982, however, both their personal and professional relationship came to an end.

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Cher then moved on to a playboy dubbed the Romeo of the Rink. Yes, in 1982 the diva began seeing Ron Duguay, an ice hockey player with the New York Rangers. But despite singing his praises while speaking to Andy Warhol for Interview magazine, Cher only managed to tame the sportsman for a month.

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Then in 1984 People magazine reported that Cher had started dating Eric Stoltz, the actor who portrayed her son in acclaimed drama Mask. However, the singer furiously denied these claims in a letter published in the national magazine. People later acknowledged that it had gotten it wrong and offered a sincere apology.

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Despite this beef with People, though, Cher was still more than happy to open up to the magazine about her next celebrity lover: Val Kilmer. In 1984 she said, “Val is terrific, but sometimes it’s just too intense and hot. It’s come the closest to working.” Cher also complimented the Top Gun star on his kissing abilities as well as his sensitivity, artistic streak and sense of humor.

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But after splitting with Kilmer, Cher then made things a little more awkward by entering into a relationship with the actor’s agent, Josh Donen. It wasn’t exactly love at first sight, though. In fact, the pair found each other difficult to get on with while Cher was dating Kilmer. They eventually found a kinship, however, and the singer later claimed to People that Donen had “the best strengths of all the men [she’s] been with.”

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But despite all this gushing, Cher and Donen were done and dusted two years later. The former then made headlines when she began stepping out with a man 18 years younger than herself: Rob Camilletti. And Camilletti, dubbed the Bagel Boy due to his bakery profession, managed to do what very few of Cher’s previous lovers had achieved.

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Yes, against all the odds, Cher and her previously unknown boyfriend managed to stay together for an impressive three years. The singer later admitted to Parade that media intrusion had had a negative impact on their relationship – but that they had stayed very good friends. She even cited Camilletti as the true love of her life during an appearance on The Marc and Myra Show.

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But there’s more. Having previously been less than discreet about her past loves, Cher chose to stay schtum about her relationship with Richie Sambora. The diva even refused to discuss life with the Bon Jovi guitarist in a 1991 interview with People. Yet she did imply that things weren’t hunky dory, admitting, “It would be very difficult to be Mr. Cher. For the last couple of years, I haven’t had much time for a private life.”

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And shortly after, Cher and Sambora parted company – reportedly over the latter’s wild rock star lifestyle. But the guitarist later told Arsenio Hall on his hit talk show that the pair’s busy work commitments were to blame. He also claimed, “We still have fun together… We still always have a good relationship, although it didn’t work out in that particular aspect.”

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News about Cher’s love life then became surprisingly scarce until 2008 – when she began dating a surprise new beau. It seems that Tim Medvetz, a member of notorious motorcycle gang Hells Angels, had captured the singer’s heart as the pair developed a bond over their passion for Harley Davidsons. And after several years of Cher and Medvetz reportedly being on/off, rumors surfaced that the unlikely couple were about to get hitched.

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But such gossip proved to be untrue, and the pair separated for good in 2013. In an interview with Notebook that same year, Cher revealed, “I just broke up with someone, but I need a little bit of a break. I don’t believe in going from one [relationship] to another. I have girlfriends that won’t leave someone they’re with until they have someone to move on to, and you just can’t do that.”

Cher also stepped out with Ron Zimmerman during one of her several breaks with Medvetz. And the screenwriter appeared to be the polar opposite of her on/off beau. She told Parade in 2010, “Ron is short, a bit scraggly, like an absent-minded professor. He’s the funniest person I have ever met, and the most eccentric – so bizarre and kind and very special.”

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In the same interview, Cher denied that she had any regrets about her eventful love life. She said, “I never felt I chose badly, and I was always happy when the next man came along. I can usually last about two years with a man, and that’s it. The moment the relationship goes into the phase of more commitment, it changes.”

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Cher has also happily discussed several one-night stands with high-profile names she’s had over the years. At the age of 16, she’s said, she hooked up with Warren Beatty – but was left disappointed. Cher told Playboy, “Not that he wasn’t technically good, or could be good, but I didn’t feel anything. So, for me, I felt, there’s no reason for you to do that again.”

And in 2010 Cher told talk show legend David Letterman about another celebrity notch on her bedpost. This time around, it was guitar legend Eric Clapton whose ears were no doubt left burning. According to the report in the Daily Mail, the pair hooked up after working together on “Love Can Build a Bridge” – a charity single released in 1995.

And then there were the ones who got away. In the same David Letterman interview, Cher confessed that she had become too nervous when Elvis Presley had asked her out and subsequently had turned the King down. She also said no to Marlon Brando when he propositioned her – a decision that she also regrets.

Of course, there’s one name in Cher’s long list of past loves that sticks out like a sore thumb. And that’s Hollywood’s ultimate sofa-jumping Scientologist Tom Cruise. Yes, Cher and the diminutive box office star briefly dated in the mid-1980s after meeting at the Malibu wedding of Madonna and Sean Penn.

A 22-year-old Cruise and a 38-year-old Cher didn’t hook up straight away, though. The pair simply got to know each other first as they continued to rub shoulders at various high-profile and star-studded events. And one such occasion was at the epicenter of American politics: the White House.

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There was a very specific reason why both Cher and Tom Cruise were in attendance. In 2018 the former told the Daily Mail, “A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic.” That same year, in fact, Cher was honored by The Lab School of Washington as an “outstanding learning disabled achiever.”

Cher told the Associated Press in 1985, “I’m a terrible reader. I don’t write letters. Numbers and I have absolutely no relationship. I can dial a phone okay, as long as it’s not long distance. I write the first letter of the word, and my mind races to the last letter. I see words and jumble them together. I see great billboards, billboards no one has ever invented.”

So it’s fair to say that Cher probably wasn’t afraid of drawing attention to herself at the White House event. A report in The Washington Post noted that the star was even “draped in black and gray gabardine with a sculpted hairstyle best described as haute punk goddess.” The same newspaper also described Cruise as sporting a “1920s-chic gangster suit” with his “hair glooped in grease.”

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Unusually, though, Cher kept quiet about her romance with Cruise until a couple of decades later. Then in a 2008 chat with Entertainment Tonight, she said, “It was a long, long time ago and neither one of us ever talked about it, and I don’t know why. When we were together, he was such a private person. He always has been until lately.”

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So it seemed that Cher felt she was able to speak about their dalliance after witnessing Cruise’s change in personality. She continued, “He didn’t mention it, and I didn’t mention it. I loved him though; he was amazing. Now it’s hard for me to look at this person and this press. How many times can I watch him jumping up and down on Oprah’s couch?”

Cher also noted, while speaking to Oprah Winfrey, just how much Cruise’s character had changed since they dated in the mid-1980s. In 2008 she told the talk show icon, “I was so crazy about him. He was so wonderful… And he was so, like, different. He was a shy boy.” Cher then revealed that she’d actually lived with Cruise in his apartment during their short-lived romance.

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So why did the unlikely pair call it a day? Well, Cher told Entertainment Tonight in 2008 that their hectic work schedules played a major part. She said, “It was after Risky Business and right before The Color of Money. I couldn’t go to Chicago and that was kind of the straw that broke the camel’s back.”

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And that wasn’t the last that we heard about the Cher/Cruise relationship. In 2013, in fact, the singer named the Mission Impossible star as one of her top five lovers during an appearance on Watch What Happens Live. She told Andy Cohen, “It was pretty hot and heavy for a little minute. The person that I knew was a great, lovable guy.”

Cher also revealed, in a 2018 interview with the Daily Mail, that the pair were still on good terms. However, the singer was keen to distance herself from Cruise’s religious beliefs. She said, “I don’t get what he does, that whole Scientology thing. I can’t understand it so I just… don’t.”

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In the same interview, Cher claimed that she now finds it harder to maintain a relationship than ever before. She said, “I’m still on the lookout. The problem I have with all the boyfriends lately is that I don’t want to go any place with them because you can’t keep a relationship going in this kind of goldfish bowl, where everything you do and every picture you have taken will be on Instagram.”

“There’s no way to keep something… special,” Cher added. The star also explained how the likes of Instagram and Twitter have made her think twice about being so candid with her relationships. She said, “I think I’m much more guarded now because of social media and because everyone has a camera. You can’t get any privacy now.”