Ben Affleck definitely has a pattern when it comes to his love life. He falls hard for famous actresses and their romances become so high profile due to the nature of two A-listers coming together. But sadly his personal demons have also got in the way of his relationships throughout the years. As the 49-year-old celebrates his marriage to Jennifer Lopez, 52, look back at his past loves here!

Gwyneth Paltrow

Gwyneth Paltrow was Ben’s first major love upon breaking big in Hollywood in the late 90s.

Ben and his bestie Matt Damon became young Hollywood royalty when the then-27-year-olds won an Oscar for Best Original Screenplay in 1998 for Good Will Hunting. It was their first effort in Hollywood and made the talented young actor-writers the hottest commodity in Tinseltown. It also landed Ben a gorgeous girlfriend in actress Gwyneth Paltrow, 48. The two were darlings of Miramax Studios Chief Harvey Weinstein and met at one of his parties in 1997, and began dating later that year.

Ben and Gwyneth co-starred in 1998’s Shakespeare in Love while very much in love themselves. Sadly, they had broken up by the time she won the Oscar for Best Actress for the film in 1999, though she thanked her “friend” Ben in her acceptance speech. The pair rekindled their romance as they starred in the 2000 drama Bounce, but ended things for good in late 2000. Over the years, the GOOP founder hinted he had issues that caused their breakup.

In 2003, Gwyneth told Diane Sawyer, “Ben makes life tough for himself. He’s got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out.” She went even further during a 2015 appearance on The Howard Stern Show, where Gwyneth put their demise on Ben, saying, “He was not in a good place in his life to have a girlfriend,” though she added that he was “super intelligent and really, really talented.”

Jennifer Lopez

Ah the romance that started one name combos. “Bennifer” became a thing during the 2002 filming of their disastrous movie bomb Gigli, while Jennifer was still married to backup dancer Cris Judd. But she and Ben could not fight their passion and fell madly in love. She divorced Cris, and Jen and Ben got engaged in late 2002. He presented her with a 6.1 carat pink diamond ring worth $2.5 million.

In 2002 Ben famously appeared in JLo’s “Jenny From the Block” music video, caressing her bikini-clad derriere while on a yacht. Between cheesy moments like that, and the high profile bomb that Gigli was, their relationship took some hits in the press and among fans. The couple became victims of overexposure, and their relationship drama came to a head when the pair called off their September 2003 wedding just a few days before it was supposed to go down. While they ended up staying together, their nuptials never happened and they called off their engagement and split for good in late Jan. 2004. Five months later, Jennifer married singer Marc Anthony on June 5, 2004, dashing any Bennifer reunion hopes.

Jennifer Garner

Like JLo, Ben didn’t stay single for long after their breakup. He admitted in a 2017 Playboy interview that he fell in love with actress Jennifer Garner, while they were filming the 2003 film Daredevil…while he was still in a relationship with Lopez! Though he didn’t act on his feelings until he and JLo had split. Ben and Garner made their relationship public on Oct. 23, 2004, kissing and cuddling in the stands at a Boston Red Sox game.

Ben proposed to Alias star Jennifer on April, 17, 2005, her 33rd birthday. They wed two months later on June 29, 2005 in a four person ceremony on the beach in the Turks and Caicos, with just the officiant and Jen’s Alias co-star and close friend Victor Garber serving as their witness. By then, Jennifer was already pregnant, and the couple welcomed daughter Violet on Dec. 1, 2005. Ben and Jen would go on to have two more children, daughter Seraphina in 2009 and son Samuel, in 2012.

Ben raised eyebrows when he left a family vacation in the Bahamas to fly to a charity poker tournament in Las Vegas on June 26, 2015 with the family’s nanny Christine Ouzounian. Though his rep strongly denied he was cheating, several days later Ben and Jen announced, “After much thought and careful consideration, we have made the difficult decision to divorce.” In a candid March 2016 interview with Vanity Fair, Jennifer said, “We had been separated for months before I ever heard about the nanny. She had nothing to do with our decision to divorce. She was not a part of the equation. Bad judgment? Yes,” on Ben’s part, but added he was still the “love of her life.” The former couple’s divorce was finalized in Oct. 2018. In a Feb. 2020 interview with the New York Times, Ben revealed, “The biggest regret of my life is this divorce.”

Lindsay Shookus

Ben stepped out with Saturday Night Live producer Lindsay in April 2017, even though he was still legally married to Jennifer. They were open about their dating as she accompanied him on a trip to London in early July 2017, and once they returned to L.A. were regularly photographed going to dinner, holding hands on outings and looking very much in love. But Ben was caught in the company of former Playboy model Shauna Sexton, taking her to dinner at Nobu Malibu on August 16, 2018, and she was photographed over the next few days coming and going from his house.

That was enough for Lindsay. On August 20, 2018, reports swirled that Lindsay had split with Ben. Two days later, estranged wife Jennifer staged an intervention and personally drove Ben to rehab in Malibu to deal with his alcoholism. Lindsay and a now-sober Ben got back together briefly in Feb. 2019 to give things another try, but broke up a few months later in April 2019.

Shauna Sexton

Ben was snapped with former Playboy model Shauna grabbing fast foot at a Jack in the Box on Aug. 19, 2018. Four days earlier, they had dinner at Nobu Malibu, even though he and Lindsay hadn’t officially split yet (though she did delete her Instagram when the photos of Ben and Shauna emerged). Apparently Ben had fallen off the wagon and was partying hard with Shauna, who was photographed arriving at his house with several bottles of alcohol.

Jennifer Garner saw Ben spiraling and staged and intervention on Aug. 22, 2018, where she personally drove a bleary eyed Ben to rehab. He spent 40 days getting clean and sober, and reunited with Shauna once he got out. The two took a romantic getaway to Montana in Oct. 2018, but they split later that month so Ben could focus on his sobriety and reconnecting with his children.

Ana de Armas

Ben and Ana met in 2019 while while filming the thriller Deep Water, and began a relationship after shooting wrapped. They were first spotted out as a couple, visiting Havana, Cuba together in early March 2020. Fans snapped photos of them shopping and looking adorable together on March 6. The jet setting couple then headed to another vacation in Costa Rica, photographed there on March 10 kissing while walking down the beach. Eight days later Ana shared photos from their getaway to Instagram. The couple then returned to L.A. just as it was entering the COVID-19 lockdown, and spent quarantine together at his house.

The couple took a local getaway to Joshua Tree, CA for Ana’s 32nd birthday on April 30, 2020. She shared IG photos of the couple cuddling, and he gave her a gorgeous diamond tennis bracelet as a birthday gift. By June, Ana had already met Ben’s three kids with Jen, as well as his mother. The actress as seemed to be a steady force in Ben’ life throughout 2020. They even had a double date to the beach in Malibu with Ben’s on-again BFF Matt and his wife Luciana on Aug. 4, 2020. Ana bought Ben a custom BMW motorcycle for his 48th birthday that month, and the couple were still on until the end of the year before calling things quits.

Jennifer Lopez 2.0

Following Jennifer and then-fiance Alex Rodriguez’s Apr. 15 2021 announcement that they were splitting up for good and better off as “friends,” Jennifer was photographed hanging out with Ben in Los Angeles on Apr. 30. While he was photographed getting out of her white SUV, at the time reports claimed that the two were just catching up on their longtime friendship. But the pair seemed to confirm that the intense chemistry they had in there initial go at romance 17 years prior was still alive and well, with a getaway to Montana together.

After J.Lo performed and Ben participated in the taping of the May 2 Vax Live event in L.A., they reportedly hopped a plane and headed to the exclusive Yellowstone Club in Montana, where they spent the week. Ben and Jen seemed very much like a “couple” a source told TMZ, which first reported the getaway. They rode in the same SUV with Ben driving and Jennifer riding shotgun in photos published by the Daily Mail. showing the pair cruising around Montana.

Things continued to heat up for Bennifer heading into the summer, which included an epic PDA-filled yacht vacation around Europe! The couple didn’t hold back their love from the world as they toured around Italy, France and Monaco, even hosting a bash for her 52nd birthday. The couple quickly began blending their families, including his three kids with ex-wife Jennifer Garner, Violet, 16, Seraphina, 13, and Samuel, 12, and her twins Max and Emme, 14.

Ben and J.Lo took a major step in April 2022 when they announced, after a year of being back together, that they were engaged! Jennifer teased the “special” news in a video via her Instagram, revealing the gorgeous green diamond engagement ring in a video shared with her OnTheJLo newsletter subscribers. The very rare diamond is estimated to be about five or six carats, and worth about $5 million.

According to the license obtained by HollywoodLife, the iconic couple made it official in Clark County, NV on Saturday, July 16. The duo wedded in Las Vegas after receiving the marriage license — but left the friends and family celebration until August 20, where they put on a fabulous fete at Ben’s estate in Georgia. Jennifer glowed in a stunning white wedding dress with a feather skirt and dramatic veil, while Ben kept it dapper in a white tuxedo suit. Their special guests included Matt Damon, Kevin Smith and a slew of family members like Ben’s mom and Jennifer’s sisters. Ben’s kids Violet, Seraphina and Sam were also in attendance, as well as Jennifer’s cute twins Emme and Max!