As Ben Affleck‘s ex-wife Jennifer Garner famously said about the actor/director, “bless his heart.” He has had so many ups and downs in every aspect of his life … from his career to romance to his ongoing battle against substance abuse. Now that Ben has reunited with former fiancée Jennifer Lopez 17 years after their engagement ended, we’re taking a look back at his highs and lows.
Ben and his childhood best friend from Boston Matt Damon were lauded as Hollywood’s brightest new kids on the block in 1998, when their film Good Will Hunting made them very young Oscar winners in 1998. The pair took home the Academy Award for Best Original Screenplay, and Ben already had a celebrity girlfriend in Gwyneth Paltrow.
The two met while filming Shakespeare in Love in 1997 and dated on and off for three years. She seemed to predict his future during a 2003 interview with ABC News’ Diane Sawyer, where Gwyneth said of her ex, “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.”
Gwyneth was apparently referring to Ben’s 2001 trip to rehab, where he was driven to the treatment facility Promises in Malibu by Charlie Sheen. “I went to rehab for being 29 and partying too much and not having a lot of boundaries and to clear my head and try to get some idea of who I wanted to be,” Affleck told The Hollywood Reporter in 2012. “It was more a ‘let me get myself straight,’ before it became a rite of passage.”
That was the same year that his relationship with J. Lo fell apart. The two met and fell hard for each other in 2001 while filming Gigli. He was so smitten that in April of 2002, he took out a gushing ad in Hollywood trade publications that read, “It has been nothing but an honor and a pleasure to work with you. I only wish I were lucky enough to be in all your movies.” It was signed, “With love, respect, and gratitude, Ben Affleck.” Four months later in July 2002, Jennifer filed for divorce from second husband Cris Judd.
The pair got engaged in November 2002, when Ben presented Jen with a custom 6.1-carat pink diamond ring from Harry Winston. He then infamously appeared in her “Jenny from the Block” music video, caressing her bikini-clad derriere aboard a yacht.
Days before their 2003 nuptials, the pair shockingly announced that they weren’t going to wed at that time, amid reports that Ben was unfaithful to Jennifer following his bachelor party at a Vancouver, B.C. strip club. While Ben never went on the record about it, actor Christian Slater‘s then-wife Ryan Haddon — who was at the bash — told Us Weekly, ”Ben did not cheat. He did not have sex with anyone. Ben was listening to music, hanging out, talking to people, that’s it.” Jennifer’s team told E! News that it was ”emphatically untrue” that she’s dumped him. Another member of J.Lo’s team told Reuters, ”They’re completely together. She knew he went to the strip club … and her attitude is: ‘What’s the big deal?’ Moving on.”
In a joint statement, the pair said, “Due to the excessive media attention surrounding our wedding, we have decided to postpone the date. When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realized that something was awry. We began to feel that the spirit of what should have been the happiest day of our lives could be compromised. We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends.” The couple never made it down the aisle, splitting up in January 2004.
Ben managed to find love again quickly, as in October 2004 he and his Daredevil costar Jennifer Garner went public with their romance, photographed putting on a PDA show at a Boston Red Sox World Series game.
The actor popped the question on Jen’s April 17, 2005, 33rd birthday, and she happily said “yes.” She was already pregnant with their daughter Violet by the time the pair wed in a Caribbean beachside ceremony on June 29, 2005. Violet arrived on December 1 of that year.
Ben and Jen went on to have two more children, welcoming daughter Seraphina in 2009 and son Samuel in 2012. The following year Ben won his second Oscar, as a producer on the film Argo. In his acceptance speech, the film’s director told the audience, “I adore you, I love you. You’re my everything” to Jen, who looked on adoringly from the front row.
Two years later, things went south when Ben made headlines for his alleged infidelity after he took the family’s nanny Christine Ouzounian to a charity poker tournament in Las Vegas on June 26, 2015, leaving Jen and their kids behind amid a family vacation in the Bahamas. Four days later, Ben and Jen announced they were splitting.
Ben denied cheating on Jennifer with the nanny, with his rep telling People, “The story is complete garbage and full of lies. It’s shameful. We are considering legal options.”
In a joint statement regarding their split, Ben and Jen said, “After much thought and careful consideration, we have made the difficult decision to divorce. We go forward with love and friendship for one another and a commitment to coparenting our children whose privacy we ask to be respected during this difficult time. This will be our only comment on this private, family matter. Thank you for understanding.”
In a candid March 2016 interview with Vanity Fair, Jen revealed, “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.” She also added about the “love” of her “life” Ben, “What am I going to do about that? He’s the most brilliant person in any room, the most charismatic, the most generous. He’s just a complicated guy.”
The pair pressed pause on their divorce in March 2017 when Ben went to rehab. In a Facebook post, he wrote, “I have completed treatment for alcohol addiction; something I’ve dealt with in the past and will continue to confront, I want to live life to the fullest and be the best father I can be.” He thanked “my co-parent, Jen, who has supported me and cared for our kids as I’ve done the work I set out to do.”
Jen helped Ben through another downward spiral in August 2018, when he was partying hard with Playboy model Shauna Sexton. She staged and intervention and personally drove him to a rehab facility in Malibu. The two finalized their divorce in October 2018.
Ben and J. Lo reignited their lost love in April 2021 and were photographed together just two weeks after her split from fiancé Alex Rodriguez. They were photographed making out on the patio of Nobu Malibu on June 13, 2021, showing that there’s always a second chance when it comes to romance.
Scroll through the photos below to see Ben’s highs and lows.
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