From 2002 to 2022! All the Similarities Between Ben Affleck and Jennifer Lopez’s Two Engagements

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From 2002 to 2022! All the Similarities Between Ben Affleck and Jennifer Lopez’s Two Engagements

History repeats itself. Nearly two decades after Ben Affleck and Jennifer Lopez first got engaged, the Oscar winner proposed once more. “Saturday night while at my favorite place on earth (in the bubble bath), my beautiful love got on one knee and proposed,” the "Dance Again" singer wrote in an April 2022 edition of her “On the JLo” newsletter. “I was taken totally off guard and just looked in his eyes smiling and crying at the same time.” She continued: "[I was] trying hard to get my head around the fact that after 20 years this was happening all over again. I was quite literally speechless and he said, ‘Is that a yes?’ I said, ‘YES of course that’s a YES.'” The Wedding Planner star smiled as she showed off her green diamond engagement ring in several photos in the newsletter. "I was smiling so big and tears were coming down my face, feeling so incredibly happy and whole," she recalled. "It was nothing fancy at all, but it was the most romantic thing I could’ve ever imagined ... just a quiet Saturday night at home, two people promising to always be there for each other. Two very lucky people. Who got a second chance at true love." After meeting on the set of Gigli in 2002, the pair soon fell in love and the Good Will Hunting star first proposed in November of that year. Their relationship was in the spotlight from the beginning and the "excessive media attention" was one of the reasons Affleck and Lopez called off their wedding just days before they were set to marry in September 2003. They called it quits four months later. [jwplayer QfzUcjHj-zhNYySv2] "I think different time, different thing, who knows what could've happened, but there was a genuine love there," Lopez told Jess Cagle in March 2016. The Argo director echoed those sentiments in a January 2022 interview with Entertainment Weekly, explaining that focus on his relationship with Lopez completely overshadowed their work on Gigli. "It became a story in and of itself. The funny name, the Jennifer Lopez romance and overexposure of that, it was kind of a perfect storm," Affleck explained. Despite becoming one of the most memorable flops of their early 2000s, he doesn't regret making the crime film. "If the reaction to Gigli hadn't happened, I probably wouldn't have ultimately decided, 'I don't really have any other avenue but to direct movies,' which has turned out to be the real love of my professional life," the Justice League star recalled. "And I did get to meet Jennifer, the relationship with whom has been really meaningful to me in my life." He reconnected with the Marry Me star in the spring of 2021, just weeks after she ended her engagement to Alex Rodriguez. "[They have] always loved each other," a source exclusively told Us Weekly in April 2021. "People close to her won’t be surprised if they end up together." The twosome confirmed that they had rekindled their romance in July 2021 via an Instagram post that reminded fans of Lopez's 2002 music video for "Jenny From the Block." While there were plenty of similarities between the two engagements, the "Get Right" performer revealed that they were making one major change this time around. "I think what we learned from the last time is that love, when you are lucky enough to find it, is so sacred and special and you have to hold a little bit of that privately and that's what we've learned," she said during a February 2022 appearance on Today. "But we're very happy, if that's what you wondering about." Keep scrolling to see all of the similarities between Bennifer's 2002 engagement and their current one: [podcast_block]

Credit: Shutterstock (2)

From 2002 to 2022! All the Similarities Between Ben Affleck and Jennifer Lopez’s Two Engagements

History repeats itself. Nearly two decades after Ben Affleck and Jennifer Lopez first got engaged, the Oscar winner proposed once more. “Saturday night while at my favorite place on earth (in the bubble bath), my beautiful love got on one knee and proposed,” the "Dance Again" singer wrote in an April 2022 edition of her “On the JLo” newsletter. “I was taken totally off guard and just looked in his eyes smiling and crying at the same time.” She continued: "[I was] trying hard to get my head around the fact that after 20 years this was happening all over again. I was quite literally speechless and he said, ‘Is that a yes?’ I said, ‘YES of course that’s a YES.'” The Wedding Planner star smiled as she showed off her green diamond engagement ring in several photos in the newsletter. "I was smiling so big and tears were coming down my face, feeling so incredibly happy and whole," she recalled. "It was nothing fancy at all, but it was the most romantic thing I could’ve ever imagined ... just a quiet Saturday night at home, two people promising to always be there for each other. Two very lucky people. Who got a second chance at true love." After meeting on the set of Gigli in 2002, the pair soon fell in love and the Good Will Hunting star first proposed in November of that year. Their relationship was in the spotlight from the beginning and the "excessive media attention" was one of the reasons Affleck and Lopez called off their wedding just days before they were set to marry in September 2003. They called it quits four months later. [jwplayer QfzUcjHj-zhNYySv2] "I think different time, different thing, who knows what could've happened, but there was a genuine love there," Lopez told Jess Cagle in March 2016. The Argo director echoed those sentiments in a January 2022 interview with Entertainment Weekly, explaining that focus on his relationship with Lopez completely overshadowed their work on Gigli. "It became a story in and of itself. The funny name, the Jennifer Lopez romance and overexposure of that, it was kind of a perfect storm," Affleck explained. Despite becoming one of the most memorable flops of their early 2000s, he doesn't regret making the crime film. "If the reaction to Gigli hadn't happened, I probably wouldn't have ultimately decided, 'I don't really have any other avenue but to direct movies,' which has turned out to be the real love of my professional life," the Justice League star recalled. "And I did get to meet Jennifer, the relationship with whom has been really meaningful to me in my life." He reconnected with the Marry Me star in the spring of 2021, just weeks after she ended her engagement to Alex Rodriguez. "[They have] always loved each other," a source exclusively told Us Weekly in April 2021. "People close to her won’t be surprised if they end up together." The twosome confirmed that they had rekindled their romance in July 2021 via an Instagram post that reminded fans of Lopez's 2002 music video for "Jenny From the Block." While there were plenty of similarities between the two engagements, the "Get Right" performer revealed that they were making one major change this time around. "I think what we learned from the last time is that love, when you are lucky enough to find it, is so sacred and special and you have to hold a little bit of that privately and that's what we've learned," she said during a February 2022 appearance on Today. "But we're very happy, if that's what you wondering about." Keep scrolling to see all of the similarities between Bennifer's 2002 engagement and their current one: [podcast_block]

Credit: Dan Steinberg/BEI/Shutterstock; Courtesy of On The JLo

The Ring

Affleck famous proposed to Lopez with a 6.1 carat pink diamond ring, which was estimated to cost $2.5 million. "I met [Barbra Streisand] at an Oscar party, years ago, and I was at the time engaged to Ben Affleck, and she’s really into diamonds, which I didn’t know,” Lopez recalled during an April 2020 interview with Zane Lowe. “He had given me a pink diamond, which got a lot of press and was whatever. I loved getting it, don’t get me wrong. So, she came up to me, and like, she’s heard of it. I’m like, ‘Oh my God.’ And she’s like, ‘Can I see your ring?'"

In 2022, the Gone Girl actor gave her a ring with an 8.5-carat green diamond, a very rare stone, with two smaller diamonds on the side. "Green has always been my lucky color and now, for sure, it always will be," the Hustlers star wrote in her newsletter shortly after the proposal. The new ring is worth an estimated $10 million. 

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The Proposal

When Affleck first popped the question, he arranged for a sentimental, private moment between him and Lopez at his parents' house in Boston. "It's just a blanket, a quilt of rose petals, all over the whole entire house. So many candles, and vases, bouquets. And my song 'Glad' was playing ... I walk in and I was just like overwhelmed. I wasn't expecting it, and I was just like 'Oh my God,'" she recalled during a November 2002 interview with ABC News. After reading her a heartfelt letter, the Daredevil star asked Lopez to marry him."That was just too much for me to handle," she said, adding that he had to remind her that she hadn't said "yes" yet. "I was like, 'Oh! Yeah! Yeah! Yes! Yes!'"

His second proposal was equally private and sentimental, taking place while Lopez was in a bubble bath.“I was smiling so big and tears were coming down my face, feeling so incredibly happy and whole,” she wrote in an April 2022 newsletter. “It was nothing fancy at all, but it was the most romantic thing I could’ve ever imagined ... just a quiet Saturday night at home, two people promising to always be there for each other. Two very lucky people. Who got a second chance at true love.” (And just like the first time, the Selena star was so speechless, she needed to be reminded to give an answer.)

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The Yacht

In her music video for "Jenny From the Block," Lopez poked fun at all of the attention her relationship with Affleck received, featuring staged paparazzi videos of the couple out on dates and relaxing on a yacht. In that infamous scene, Affleck is seen caressing her back and behind before untying her bikini top.

The "Jenny From the Block" video was top of everyone's mind in July 2021, when Lopez shared photos from a trip they took to the South of France in honor of her 52nd birthday. "We were just on the boat! There was no recreation!" Lopez told People in February 2022 about the comparisons between the two boat outings. "I was lying down. ... It was a trip I like to take for my birthday, but no, we were not intentionally recreating it. I didn't know there were paparazzi out in the middle of the ocean either!"

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The Music Videos

After costarring in "Jenny From the Block" 20 years earlier, Affleck made another cameo in one of Lopez's music videos. However, for the "Marry Me" video, which was released in March 2022, the screenwriter had a much more subtle presence, with just his arm and neck visible in the final shot.

The Last Duel star also gifted Lopez with a remixed video for her single, "On My Way," for Valentine's Day. “I am going to share something very special and personal with you that normally that I would only share with my inner circle,” Lopez wrote via her OnTheJLo newsletter in February 2022. “It’s an early Valentine’s Day present from Ben. Watching it made me think about the journey of true love, it’s unexpected twists and turns, and that when it’s real, it actually can last forever. This seriously melted my heart."

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The Red Carpet Moments

The couple formerly known as "Bennifer" made their red carpet debut at the premiere of Maid in Manhattan back in 2002. For the event, Lopez wore a ruffled, cream dress with a white fur coat and she and Affleck gazed lovingly at one another on the red carpet.

In September 2021, they made their first red carpet outing together since 2003 at the Venice International Film Festival premiere of The Last Duel. Just like the first time, Lopez wore white and the pair only had eyes for one another as they posed for photographers.

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The Friendship

“You can’t pinpoint [the moment we fell in love]. We became friends first. That is the honest to God truth," Lopez told Dateline's Pat O'Brien about the origins of their romance in 2002. Nineteen years later, a source told Us that they have "always remained friends," and it was easy for them to reconnect in 2021. "[Ben and Jennifer] had a heart-to-heart and it reignited the spark between them," another source told Us, noting things have “progressed” into something more.

In both instances, Lopez was getting out of a serious relationship when she and Affleck fell in love. In June 2002, she filed for divorce from dancer Cris Judd and made her relationship with the Pearl Harbor actor public afterward. She and Affleck later reconnected in April 2021, just weeks after she and Rodriguez announced that they had ended their engagement.  

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The Gushing Interviews

"This is somebody who nobody ever said like, 'Hey kid, you’re going to be a star. You’ve got what it takes,'" Affleck gushed in a 2002 interview with NBC News. "She didn’t look like how people were supposed to look, she didn’t have the body shape that women were supposed to have, and rather than changing herself or trying to be something else, she said, 'This is who I am,' and she believed in herself."

The Massachusetts native was effusive about Lopez's success again in September 2021 when she was named Adweek's 2021 Brand Visionary. "I am in awe of what Jennifer's effect on the world is. At most, as an artist, I can make movies that move people," Affleck said at the time. "Jennifer has inspired a massive group of people to feel they have a seat at the table in this country. That is an effect few people throughout history have had, one I will never know and one I can only stand by and admire with respect."