Ben Affleck’s love life has come full circle with his marriage to Jennifer Lopez.

The actor and director has had his fair share of high-profile romances throughout his career, from his relationship with his Shakespeare in Love costar Gwyneth Paltrow to his marriage to Jennifer Garner. However, when it comes to making headlines, Affleck’s longtime connection with his now-wife, Lopez, has captured the height of public attention.

When Affleck and Lopez began dating and got engaged in 2002, the media coverage was relentless. As they planned their wedding, the spotlight put pressure on their upcoming nuptials — and it got to be too much. The couple postponed their wedding less than a week before the big day; a few months later, they called off their engagement.

Affleck went on to marry Garner, with whom he welcomed three children, though the pair ultimately split in 2015. Six years later, Affleck and Lopez reconnected and decided to give their love a second chance — which turned into their long-awaited moment to say “I do” in 2022.

“I am very lucky in my life in that I have benefited from second chances, and I am aware that other people don’t even get first chances,” Affleck shared with WSJ. Magazine. “Life is difficult, and we are always failing and hopefully learning from those failures. … I haven’t always been successful, but in cases in which I have, they’ve turned out to be the defining aspects of my life.”

Fast forward to May 2024, sources told PEOPLE that Affleck and Lopez’s marriage “is not in the best place at the moment” and the two were living separately. The news comes after the actor and singer weren’t seen together in public for over a month. The two have subsequently attended different events on their own.

According to a music source, the way they share their lives differs. “She likes to open her heart to her fans and to the world,” they said. “He is more introspective and private. This has been difficult day-to-day.”

Here’s a look back at Ben Affleck’s dating history.

Cheyenne Rothman

Ben Affleck and Cheyenne Rothman at the premiere of ‘Chasing Amy’ on March 26, 1997 in Los Angeles, California. KATHY HUTCHINS/HUTCHINS PHOTO/NEWSCOM/MEGA

Before Affleck made it big, he met Cheyenne Rothman as a teenager in the early ’90s.

The pair first crossed paths while attending the same summer camp and dated for several years. Rothman even accompanied Affleck to the premiere of Chasing Amy in early 1997, but by that summer, their relationship was officially over.

Gwyneth Paltrow

Ben Afleck and Gwyneth Paltrow. KEVIN MAZUR ARCHIVE/WIREIMAGE

In 1997, Affleck was introduced to Paltrow at a dinner hosted by now-disgraced studio mogul Harvey Weinstein. They were both cast in Shakespeare in Love and by 1998, they were an item. The couple were first spotted on the red carpet at a Golden Globes afterparty hosted by Miramax Films.

Affleck and Paltrow dated while filming Shakespeare in Love, but their relationship was not without challenges. Looking back, Paltrow said the actor was not ready for a relationship.

“I think [my parents] appreciated how he’s super intelligent and he’s really, really talented and so funny, but he was not in a good place in his life to have a girlfriend. I think they were okay with the two of us not being together,” she told Howard Stern in 2018.

Affleck and Paltrow called it quits at the end of 1998 — but it wasn’t the end. Just a few months later, they were both cast in Bounce and soon sparked reconciliation rumors. While doing press for the film in June 1999, Affleck maintained that he was single; in October, the pair were spotted kissing in Paris. They continued dating for another year before breaking up in October 2000.

Affleck and Paltrow have remained friendly throughout the years — and she congratulated Affleck on his marriage to Lopez in 2022.

Jennifer Lopez

Ben Affleck and Jennifer Lopez at the premiere of ‘DareDevil’ in Westwood, California. GREGG DEGUIRE/WIREIMAGE

Affleck first met Lopez on the set of the movie Gigli in 2002, and at the time, she was married to choreographer Cris Judd. After less than a year as husband and wife, Lopez filed for divorce in July 2002 amid rumors that she had been getting close to Affleck.

It wasn’t long before things got serious between the pair, and they took their romance public. “I really felt like when I met Ben, ‘Okay, this is it,’ ” Lopez told PEOPLE in 2016.

The duo, known as “Bennifer,” quickly became one of the most famous couples in the world as paparazzi followed their every move. While Affleck and Lopez didn’t intend to have a public relationship, Lopez recalled that they “just happened to be together at the birth of the tabloids.”

Cameras captured the couple’s blossoming romance leading to their engagement in November 2002. Affleck surprised Lopez with a pink diamond in a proposal that his new fiancée called “very, very beautiful.”

The following year, Affleck and Lopez began to plan their wedding while working on their second movie together, Jersey Girl. That summer, their film Gigli premiered in theaters, and despite the media attention around the couple, it only earned $7 million off a $75 million production budget, per IndieWire.

In September 2003, the pair announced that they were postponing the wedding — just four days ahead of the ceremony.

“Due to the excessive media attention surrounding our wedding, we have decided to postpone the date,” they said in a statement. “When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realized that something was awry. We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends.”

The couple officially called off their engagement in January 2004. Reflecting on their split years later, Lopez said the coverage surrounding their relationship played a major role in their breakup.

“We were so in love,” she told Rolling Stone in 2022. “But also, there was this other thing happening where we were being criticized, and it really destroyed our relationship from the inside out because we were just too young to understand at that time what were really the most important things in life.”

Ben Affleck and Jennifer Lopez attend ‘The Last Duel’ New York premiere on October 09, 2021 in New York City. ASTRID STAWIARZ/GETTY

They remained on good terms, often complimenting each other in the media. Affleck and Lopez pursued other relationships, got married and welcomed children — but it wasn’t the end of their history together.

In April 2021, Affleck sent an email to Lopez, and soon the former couple were spending time together in Los Angeles and on vacation in Montana, sparking rumors that they had rekindled their romance.

Later that same July, the couple confirmed their romance when Lopez shared a photo of the pair kissing on her 52nd birthday. Their relationship quickly heated up, and in September, they walked their first red carpet together since reuniting.

“I feel so lucky and happy and proud to be with him,” Lopez told PEOPLE in February 2022 for the Love Issue. “It’s a beautiful love story that we got a second chance.”

Just two months later, the couple were engaged, with Lopez confirming that Affleck popped the question for the second time in her newsletter. In July, Affleck and Lopez officially tied the knot in a small, private ceremony in Las Vegas; Lopez called it the “best night ever.”

That August, they celebrated their marriage with a larger ceremony at Affleck’s estate in Georgia. The celeb-studded event included friends like Matt Damon, Kevin Smith and Jason Mewes. “Some old wounds were healed that day and the weight of the past finally lifted off our shoulders,” Lopez wrote in her newsletter. “Full-circle — and not at all the way we planned it. Better.”

After the wedding, they jetted off for an Italian honeymoon, where they were spotted shopping and dining. Lopez later shared that she took Affleck’s last name.

Looking back at where they started and how it worked out, Lopez expressed gratitude during an interview with Apple Music 1’s Zane Lowe in 2022.

“Once we called off that wedding 20 years ago, it was the biggest heartbreak of my life,” she said. “Now, 20 years later, it does have a happy ending. It has the most would-never-happen-in-Hollywood ending.”

Ben Affleck and Jennifer Lopez attend the Los Angeles premiere of Amazon MGM Studios ‘This Is Me…Now: A Love Story’ on February 13, 2024 in Hollywood, California.JON KOPALOFF/WIREIMAGE

However, in May 2024, sources told PEOPLE that their marriage “is not in the best place at the moment” as they navigate living under the public eye. After not being spotted together for over a month, multiple sources confirmed that they were living separately. But afterward, the two were spotted attending an event in L.A. and walking around West Hollywood.

Another source elaborated on how the actor and singer’s views on publicity had affected them.

“They just have very different approaches when it comes to media attention,” the source said. “Ben hates all attention and it makes him very uncomfortable. Jennifer has always had a different approach.”

Jennifer Garner

Jennifer Garner and Ben Affleck at an event on February 13, 2003.SYLVAIN GABOURY/FILMMAGIC

Affleck and Garner met for the first time while they were filming Pearl Harbor in 2000, but they remained professional as Garner was married to her Felicity costar Scott Foley. She and Affleck didn’t truly connect until 2003 when they became close friends working on Daredevil.

After Affleck and Garner had both split from their partners, the pair began corresponding over email — Garner later told Parade that Affleck was a “very persuasive writer.” In October 2004, the duo went public with their relationship at a World Series game. Their relationship moved quickly, and on Garner’s birthday in April 2005, Affleck popped the question.

Two months later, the couple wed in a private ceremony in Turks and Caicos on June 29, 2005, and confirmed that they were expecting their first child. Affleck and Garner welcomed their daughter, Violet Anne Affleck, on Dec. 1, 2005, followed by their second child, Seraphina Rose Elizabeth Affleck, on Jan. 6, 2009. Their son Samuel Garner Affleck completed the family of five with his birth on Feb. 27, 2012.

“There’s nothing more emotional than seeing your partner — the man you love — with your baby at any time: the first time, the second, yesterday, today. There’s nothing more beautiful,” Garner told PEOPLE in 2007.

The private pair kept a low profile while raising their young children and often shared sweet sentiments about each other in interviews. But behind the scenes, there were challenges. In June 2015, they announced they were divorcing.

“After much thought and careful consideration, we have made the difficult decision to divorce,” the couple said in a joint statement. “We go forward with love and friendship for one another and a commitment to co-parenting our children whose privacy we ask to be respected during this difficult time.”

Ben Affleck and Jennifer Garner attend the 2014 Vanity Fair Oscar Party on March 2, 2014 in West Hollywood, California. JEFF VESPA/VF14/WIREIMAGE

Following the split, Affleck and Garner showed a united front, vacationing in the Bahamas and celebrating Affleck’s 43rd birthday with their kids.

In February 2016, Garner opened up about their split for the first time, despite previously taking a personal “oath” to avoid the media. In a Vanity Fair interview, Garner said, “He’s the love of my life. … He’s just a complicated guy.”

The following year, in March 2017, Garner supported Affleck as he entered treatment for alcohol addiction. (He previously sought help in 2001). In an emotional statement posted on Facebook, he thanked Garner, who had “supported” him and looked after their children while he cared for himself. Shortly after Affleck’s rehab stay, the former couple officially filed for divorce.

In August 2018, when Affleck entered rehab, Garner was by his side and even dropped him off at the facility. After completing his 40-day stay, the pair finalized their divorce.

Less than two years later, the Good Will Hunting star reflected on their split, calling their divorce “the biggest regret” of his life and noted that his drinking played a role in his “marital problems” with Garner. In a separate interview, Affleck shared that he didn’t think he would ever divorce or have a “split family.”

Affleck later told PEOPLE that he and Garner would always be in each other’s lives because of their children. “When you have children with somebody you’re connected to them forever,” he said. “And I’m very lucky she is the mother of my children. I’m very grateful and respectful of her.”

In 2021, Affleck opened up about his divorce from Garner on The Howard Stern Show. The actor told Stern that part of the reason he started drinking was that he felt “trapped” in an unhappy marriage — and would “probably still be drinking” if they stayed together. Days later, Affleck clarified his comments, saying that his words had been taken out of context.

“I would never want my kids to think I would ever say a bad word about their mom,” he said. “I had gone on and said how much we respect each other and cared about each other and cared about our kids and put them first.”

Today, Affleck and Garner are often seen grabbing coffee and spending time with their children. According to The Hollywood Reporter, the actress is in talks to star in Affleck’s upcoming crime thriller Animals for Netflix.

Lindsay Shookus

Ben Affleck and Lindsay Shookus attend the 2017 U.S. Open Tennis Championships on September 10, 2017 in New York City. JACKSON LEE/WIREIMAGE

In 2017, Affleck went public with his relationship with Saturday Night Live producer Lindsay Shookus — but the pair had reportedly known each other for years.

Sources told PEOPLE that after meeting on the set of SNL, Affleck and Shookus became close, although they were both still married. After Affleck hosted the show in May 2013, the pair were spotted acting flirty at a movie premiere afterparty. In the following years, Affleck often visited Shookus at SNL whenever he was appearing on The Tonight Show.

Affleck and Shookus were spotted in London in June 2017, after which they jetted back to L.A., where Shookus reportedly stayed at Affleck’s home.

The two continued to date throughout the year; they were spotted on numerous outings in L.A. and New York City. They also vacationed in Maine, and Affleck even accompanied Shookus to the Emmy Awards. Early in 2018, Affleck and Shookus took a trip to Hawaii, and shortly after, she made her first comment about their romance.

“It’s strange to me,” Shookus told Elle of having a high-profile relationship. “My entire career has been behind the camera, and that’s definitely where I’m most comfortable. I’m a producer, I’m a mom, a friend. Being considered a public figure honestly makes me laugh.”

By the summer of 2018, Affleck had met Shookus’ parents, and sources told PEOPLE that he was “very happy” to have her in L.A. between SNL seasons. Still, dating long-distance was tough, and the pair broke up in August. Sources shared that Affleck’s addiction played a role in the split.

“It was very hard for her to break up with Ben, but she knew he wasn’t getting better and that it was time for her to step aside,” a source told PEOPLE. “All she wanted was for him to be happy and healthy. It was a difficult choice but the right one.”

Just a week later, amid rumors that Affleck was dating Playboy model Shauna Sexton, he entered rehab and leaned on Garner for support.

A few months after he completed treatment and stopped seeing Sexton, Affleck and Shookus started “spending time together” and were officially back together by March 2019. Their rekindled romance didn’t last long, though, and they split for the second time that same April.

“She has a kid and an ex-husband and a job in New York and Ben has his family and a job in L.A. and while they love and respect each other they just realized it wasn’t going to work,” a source told PEOPLE. “They really gave it another solid try.”

Shauna Sexton

Ben Affleck and Shauna Sexton getting food. LASTARPIX/BACKGRID

In the weeks after Affleck’s split from Shookus, Affleck and Playboy model Shauna Sexton were spotted leaving Nobu restaurant together. In the days that followed, Affleck and Sexton were seen on several occasions, including a trip to fast-food joint Jack in the Box and spending time at Affleck’s home.

But only days after the pair were first spotted together, Affleck entered rehab for alcohol addiction — amid accusations that Sexton had gotten him “thrown in rehab” after drinking with the actor. Sexton denied the claims, sharing that she would never “disrespect someone’s hard-earned sobriety by drinking with them or in front of them.”

Throughout Affleck’s stay in rehab, the duo continued to get to know each other: Sexton visited him at his treatment facility in Malibu, Calif., and spent time at his house when he went home to work out with his trainers. When Affleck completed treatment in October, they continued to date and even took a trip to Montana before calling it quits two days later.

“He enjoyed being with her but is working on himself, and being together with her at this time is not something that works,” a source told PEOPLE. “He will date in the future, but for now his focus is on his sobriety, family and his next project.”

Ana de Armas

Ben Affleck and Ana de Armas walking together on April 12, 2020 in Los Angeles, California. BG004/BAUER-GRIFFIN/GC IMAGES

In November 2019, Affleck met costar Ana de Armas while working on the movie Deep Water. Sources told PEOPLE the pair had “great chemistry right from the start,” and after filming wrapped, things took a romantic turn.

Fast forward to March 2020, they spent time together in de Armas’ hometown of Havana, Cuba and the pair later jetted to Costa Rica where they were seen taking a sunset stroll on the beach.

“Ana was his tour guide and took him to all her favorite places. Ben seemed to love the trip. He was in a great mood and very friendly,” a source told PEOPLE. “They are definitely dating.”

The COVID-19 pandemic lockdown began shortly after the pair returned to L.A. and the couple quarantined together at Affleck’s home. They were often spotted on walks around the neighborhood.

“They seem to have a great time together,” a source said of the duo. “They order delivery food and groceries and only leave the house for walks around the neighborhood with their dogs. Ben looks incredibly happy. They are flirty and goofy. Ana always has a huge smile around him.”

In April 2020, the couple made their relationship Instagram official with photos of a socially distanced desert getaway for de Armas’ birthday. By May, they were “very serious,” and Affleck reportedly wanted de Armas to get to know his children. Shortly after, photos surfaced of the couple spending time with his kids, who later played a prank on their dad by leaving a cardboard cutout of de Armas on his lawn. A source told PEOPLE that they were “enjoying their time together.”

Later that summer, de Armas joined Affleck, his mom and his kids on a vacation to Georgia, and she gifted him a motorcycle for his 48th birthday. In August, de Armas reportedly moved into Affleck’s home; that November, they spent Thanksgiving with Affleck’s children, with sources saying they “seemed very happy.”

Despite the couple’s holiday plans, Affleck and de Armas decided to go their separate ways in the new year. Sources told PEOPLE that they decided to amicably split after almost a year together because they were at “different points in their lives.”

“She broke it off. Their relationship was complicated. Ana doesn’t want to be Los Angeles based and Ben obviously has to since his kids live in Los Angeles,” a source told PEOPLE. Another source added, “This is something that was mutual and something that is completely amicable.”