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They postponed their wedding in September 2003 and officially split in January 2004.
Lopez confirmed their rekindled relationship by posting a photo of them kissing in July 2021.
2001: Lopez and Affleck began filming the movie "Gigli."
Affleck starred as the titular character, a mobster named Larry Gigli, and Lopez portrayed a gangster named Ricki.
Predictably, their characters fell in love and ended up together by the conclusion of the critically-panned movie.
At the time, Lopez was married to Cris Judd, her second husband (she was briefly married to Ojani Noa prior to that). She and Judd met on the set of her music video for "Love Don't Cost a Thing" and wed in September 2001.
In an interview with Vanity Fair for a feature released in March 2003, Affleck denied speculation that he and Lopez acted romantic with each other while she was married.
"When I met her we became really, really, really good friends," Affleck said.
He continued: "But at first, because she was married, there was no thought of a romantic relationship, so that created the opportunity to get to know each other without any of the falseness that goes with courtship because you're trying to make a good impression."
Affleck said that neither of them changed aspects of themselves, and they "became really good friends in a way that was very comfortable."
"With Jen, I thought, Even though it can never happen, it was nice for me to know I was capable of feeling that way — that I could love somebody in a way where what I really wanted was for them to be happy, even more than I wanted what I wanted," he added. "That was a new experience for me."
April 2002: Ben Affleck took out ads in Variety and The Hollywood Reporter, in which he gushed about working with Lopez on "Gigli."
Affleck wrote: "You have shown kindness, dedication, diligence, humility, graciousness of spirit, beauty in courage, great empathy, astonishing talent, real poise and true grace...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.''
He also signed the ad: ''With love, respect and gratitude, Ben Affleck.''
Of the big gesture, Affleck later told Vanity Fair that Lopez "had developed this reputation as a diva and a pain in the a--," and he wanted to publicly voice his support of her and "counteract" that narrative.
"She works harder than anybody I've ever seen," he said. "I thought/was busy with movies and television and writing; I felt pretty maxed out until I met her. She was doing all that and recording albums on weekends!"
July 2002: Lopez filed for divorce from Judd, a month after breakup reports spread. She and Affleck went public with their relationship that summer.
Lopez cited irreconcilable differences as their reason for ending their marriage.
"Jennifer Lopez and Cris Judd have announced they have resolved all issues arising out of their marriage. The resolution was extremely amicable," their lawyer said in a statement shared by People.
Affleck told Vanity Fair that he wasn't aware of marital issues between Lopez and Judd because she never mentioned it during their conversations.
"We would hang out, but I talked about me all the time: 'Enough about you!' I was vaguely aware she had something going on, but I was too busy running off my mouth," he said.
"It changed when she told me she was getting separated," Affleck said about when things changed between them. "At that point, it became a possibility; doors were opened."
November 5, 2002: Lopez released her music video for "Jenny From the Block," starring her and Affleck.
The music video drew inspiration from the couple's real-life experience of being scrutinized by the public and being hounded by paparazzi.
It showed them making out on a yacht and holding up a tabloid that included chatter about them.
That month, Lopez and Affleck were spotted filming their second movie together, "Jersey Girl," in New York City and New Jersey.
The film was directed by Kevin Smith, who later said that he coined the term "Bennifer" — the couple's hybrid nickname. Smith said he gave Lopez and Affleck the moniker "during 'Jersey Girl' pre-production, before the world found out they were dating."
In the movie, Lopez portrayed Affleck's wife who died while giving birth to their daughter.
November 11, 2002: Their engagement was confirmed during the couple's interview with Diane Sawyer as part of ABC's "PrimeTime: Special Edition."
"It's just a blanket, a quilt of rose petals, all over the whole entire house," Lopez said of the unexpected proposal that took place in Boston. "So many candles, and vases, bouquets. And my song 'Glad' was playing ... I walk in and I was just overwhelmed. I wasn't expecting it, and I was just like 'Oh my God.'"
Lopez said that she began "sobbing" as he read a handwritten letter listing the reasons why he loved her and wanted to spend the rest of his life with her. She got even more emotional when she saw the pink diamond, which was her favorite stone.
"I had cried a lot over sadness over the years," she said during the interview. "And for the first time in my life, I cried incredible purging tears of happiness. It was the most cleansing feeling and the most wonderful feeling I had ever had."
The "On the Floor" singer also described Affleck as "brilliantly smart…. Loving. Charming. Affectionate. And I just admire him in every way. I respect him. I feel like he teaches me things." crazy life and needing a sense of security."
November 26, 2002: Lopez's third studio album was released, drawing inspiration from her relationship with Affleck.
"This Is Me... Then" featured tracks like "Jenny From the Block" and "All I Have." The album also included a song called "Dear Ben," which was a love letter to the actor.
February 9, 2003: The couple attended the LA premiere of Affleck's film "Daredevil."
The event took place at the Village Theatre in Los Angeles, California and the film was released on February 14.
Affleck also posed on the red carpet with costars Colin Farrell, Michael Clarke Duncan, and Jennifer Garner — who he'd go on to marry.
At the time, Garner was married to "Felicity" costar Scott Foley. Their nuptials took place in October 2000 and Garner filed for divorce in May 2003. Foley later told TV Guide that there was no infidelity involved.
March 2003: In his Vanity Fair feature, Affleck said that Lopez made him a better person and he was excited to marry her.
"Jennifer is a really wonderful, fabulous woman, smart and interesting," he told the publication. "Spending time with her makes me a better person and a happier person. She impresses me every day. It feels better to me to be with her than without her."
He added: "Jen and I want to get married for the reason everyone else does: we fell in love. I'm in love; I want to have a family; and she's the only person I've ever met who made me entertain the thought of doing that."
The "Gone Girl" star said that he didn't understand the public's obsession with the relationship, but had an idea why people were so interested.
"I think it has to do with race and class, the fact that I'm white and she's Puerto Rican," he said. "That's what's underneath, although nobody says it, because it's not politically correct."
Affleck also said that people made incorrect assumptions about Lopez's romantic life because she was "characterized as oversexed."
"Jen has had fewer boyfriends than your average high-school junior," he said. "In the physical sense, she's extremely chaste."
He added: "She's had a much simpler, more easily explainable, more clean romantic history than I have. She can tell the whole story in 15 minutes, whereas I always preface the whole story with 'It was complicated ...'"
Affleck also said that race was a factor, because "there's a kind of language that's used about her — the spicy Latina, the tempestuous diva. She's characterized as oversexed."
"She's a deeply misunderstood woman, in my opinion," he said.
July 2003: The couple participated in a joint interview as a couple to promote "Gigli," though much of the questions were about their romance.
During the hour-long "Dateline" NBC special hosted by Pat O'Brien of "Access Hollywood," the couple recalled not really knowing each other prior to working together on "Gigli."
"We met at a couple of the parties," Lopez said. "You know, we barely paid any attention to each other at all."
Lopez insisted that they were "really good friends" on the set of "Gigli."
"We talked a lot and that's the thing," she said. "There was no kind of idea that we would be together in the future, so it was one of those things where you kind of like say too much."
She added: "It felt like we had good chemistry. He likes to improv. I could improv back. He's the best person to improv in the whole entire business, he's so funny."
Lopez also said that there wasn't an exact moment when they fell in love.
"You can't pinpoint it. It was like we became friends first, that is the honest-to-god truth," she said.
Elsewhere in the interview, the singer said that she'd maintain her surname professionally, but would technically take Affleck's last name.
Affleck, a Boston native and vocal Red Sox fan, also said that he was opposed to their family being supporters of the New York Yankees — the team that originates in Lopez's hometown.
"The Mets is fine. I could put up with the Mets. The Mets I could live with," he said. "Pinstripes can't be in the house."
August 1, 2003: "Gigli" was released in theaters and famously flopped at the box office.
In the years that followed, Lopez spoke about the difficulties that followed.
"I think the worst, probably lowest point was the whole 'Gigli' era. It was pretty tough," she said in a 2015 interview with "HuffPost Live," according to E! News.
"It was a very badly reviewed film," she elaborated. "I was in a high-profile relationship at the time that fell apart in a really bad way, and so the kind of mix of those two things and the tabloid press had just come into existence at the time, so I was like a poster child for that moment."
She added: "I was in the tabloids every other week about how my life was falling apart. It was a tough time."
Despite the hardships, Lopez said that she had "no regrets."
"I would do it all over again, I think," she said. "I really would. Even the relationship part. "
In an interview with Vanity Fair in 2017, the star said that she was "eviscerated" by that period in her life.
"I lost my sense of self, questioned if I belonged in this business, thought maybe I did suck at everything," she said. "And my relationship [with Affleck] self-destructed in front of the entire world. It was a two-year thing for me until I picked myself up again."
September 2003: Lopez and Affleck's wedding was postponed because of public attention.
According to People, the couple was supposed to wed in Santa Barbara but pushed it back shortly before the planned date.
"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."
They continued: "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."
January 2004: Their split was officially announced.
The announcement wasn't entirely surprising to fans, who noticed that Affleck went solo to events and Lopez was spotted sans her engagement ring.
"Jennifer Lopez has ended her engagement to Ben Affleck," a rep for the singer said, per People. "At this difficult time, we ask that you respect her privacy."
March 26, 2004: Their film "Jersey Girl" was released in theaters.
While it wasn't as despised by critics as "Gigli," the film still received poor reviews.
June 5, 2004: Lopez married Marc Anthony in Los Angeles.
The ceremony took place in her Beverly Hills home and had a small guest list.
Lopez and Anthony welcomed twins named Max and Emme on February 22, 2008.
In July 2011, the pair revealed their split.
"This was a very difficult decision," they said in a joint statement. "We have come to an amicable conclusion on all matters. It is a painful time for all involved and we appreciate the respect of our privacy at this time."
June 2005: Affleck married Garner in a low-key wedding ceremony that took place in Turks and Caicos.
A few months later, in December 2005, the couple welcomed their first child, a daughter named Violet.
Garner gave birth to two more children: daughter Seraphina in January 2009 and son Samuel in February 2012.
In June 2015, the couple revealed their breakup after being married for a decade.
"After much thought and careful consideration, we have made the difficult decision to divorce," their statement to People read. "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."
May 3, 2010: During an appearance on "The Graham Norton Show," Lopez said that her relationship with Affleck "did suffer" because of the media's attention.
"I love Ben, he's a great guy, but it was a lot for both of us to be under that type of siege for two years straight," she said. "We were on the cover of every magazine, every week, it was just a weird thing."
Lopez continued: "Our relationship, I think, did suffer because of that. That's not the only reason. I would never blame the media for anything, but I think it definitely played a part in the dynamic of our relationship."
January 25, 2013: Lopez said that she and Affleck still communicated, mostly via email.
Appearing on Katie Couric's talk show titled "Katie," the singer said that it wasn't awkward running into exes Diddy and Affleck at the Golden Globes that year.
"We run in the same circles," she said. "I do see them. The world doesn't know that I see them. I don't go, 'Hey, I ran into Diddy today.' I don't tweet that kind of stuff. But I do run into them."
"We talk and we email, more email than anything," Lopez added of keeping in touch with Affleck.
Lopez said that she was "happy" for Affleck after his film "Argo," which he directed, produced, and starred in, won two awards at the event: best drama motion picture and best director.
The singer called the film "one of the best pictures of the year" and said that she gave him a standing ovation when he won.
November 4, 2014: Lopez opened up about her romantic history in her memoir titled "True Love."
"Ben and I split up at the moment when I thought we were committing to each other forever, it was my first real heartbreak, it felt like my heart had been torn out of my chest," she wrote, per Page Six.
Lopez said that she "sought out comfort in another person."
"Marc came back into my life three days after I should have been at the altar saying 'I do' to another man," she wrote.
March 2016: Lopez said that she and Affleck had "genuine love" for each other.
"We didn't try to have a public relationship," she said in an interview with Jess Cagle, the editorial director at People and Entertainment Weekly. "We just happened to be together at the birth of the tabloids, and it was like 'Oh my God.' It was just a lot of pressure."
She added: "I think different time different thing, who knows what could've happened, but there was a genuine love there."
January 2019: Lopez said that tabloid attention "absolutely" led to their breakup.
"When the tabloids were out and we were being hounded by paparazzi constantly, it was a really hard time," she said during part one of her documentary for MTV called "The Ride."
"I remember being on the cover of those tabloids for two years straight and it was brutal," she added. "I think it absolutely contributed to the demise of our relationship and the love that we had. There was so much judgment and pressure and scrutiny and opinions and it was just a really, really hard thing to deal with."
She shared similar thoughts months later during an interview with "CBS This Morning," in which she said that the media attention was "scary" and "overwhelming" for her and Affleck.
February 18, 2020: Affleck said that Lopez should have been nominated for an Oscar for her performance in "Hustlers."
He praised his ex during an interview with the New York Times, but the quotes never made it into the feature. The reporter, Brooks Barnes, shared the comment in a Twitter thread with other quotes that didn't make the cut.
"She should have been nominated," Affleck said. "She's the real thing. I keep in touch periodically with her and have a lot of respect for her. How awesome is it that she had her biggest hit movie at 50? That's f---ing baller."
January 4, 2021: Affleck said that people said sexist and racist things about Lopez that wouldn't be acceptable today.
"People were so f---ing mean about her — sexist, racist," he said during The Hollywood Reporter's "Awards Chatter" podcast. "Ugly, vicious shit was written about her in ways that if you wrote it now you would literally be fired for saying those things you said."
Affleck said that nowadays, Lopez is more respected for her achievements.
"I would say you have a better shot, coming from the Bronx, of ending up as [Justice Sonia] Sotomayor on the Supreme Court than you do of having Jennifer Lopez's career and being who she is at 50 years old today," he said.
January 18, 2021: Multiple outlets reported that Affleck and "Knives Out" star Ana de Armas broke up after dating for less than a year.
The two stars met while filming the upcoming psychological thriller "Deep Water" in New Orleans, Louisiana, in 2019.
Throughout the pandemic, they were frequently photographed while going on walks together in LA. The actress also spent time with Affleck's kids that he shares with Garner.
De Armas made their relationship Instagram official in April 2020 when she posted a photo of the "Justice League" star with his arms around her waist, celebrating her 32nd birthday.
After their breakup was revealed, paparazzi saw a life-size cutout of de Armas being thrown in Affleck's trash bin. The same one was previously seen on Affleck's lawn in June 2020, seemingly as part of a prank that his kids pulled on him.
April 5, 2021: Affleck spoke about Lopez's work ethic and agelessness in her May 2021 cover story for InStyle.
Affleck was one of several friends and costars of Lopez who spoke highly of the entertainer.
"I thought I had a good work ethic, but I was completely humbled and blown away by what she was committed to doing day in and day out, the seriousness in which she took her work, the quiet and dedicated way she went about accomplishing her goals, and then how she would go back and redouble her efforts," Affleck said.
The actor continued: "She remains, to this day, the hardest-working person I've come across in this business. She has great talent, but she has also worked very hard for her success, and I'm so happy for her that she seems, at long last, to be getting the credit she deserves."
Joking about the singer seemingly being ageless, Affleck said, "Where are you keeping the fountain of youth? Why do you look the same as you did in 2003 and it kind of looks like I'm in my 40s…at best?"
April 15, 2021: Lopez and Alex Rodriguez confirmed that they split up after four years together.
"We have realized we are better as friends and look forward to remaining so," they said. "We will continue to work together and support each other on our shared businesses and projects. We wish the best for each other and one another's children. Out of respect for them, the only other comment we have to say is thank you to everyone who has sent kind words and support."
April 30, 2021: Page Six reported that Lopez and Affleck were spending time together at her LA home.
According to the publication, Affleck was reportedly "picked up in a white Escalade SUV that allegedly belongs to Lopez and then taken to her nearby mansion."
"They have a great time hanging out," a source told People a few days after photos were first published of the two stars in separate vehicles. "It's been years since they caught up properly. They have lots to talk about."
Affleck and Lopez also participated in Global Citizen's "Vax Live: The Concert to Reunite the World," which aired on Saturday, May 2. Lopez performed, while Affleck spoke on stage with Jimmy Kimmel. The two weren't photographed together at the taping, which took place in California.
May 10, 2021: People reported that they "spent several days" together in Montana.
"They have a strong connection. It's all been quick and intense, but Jennifer is happy," an anonymous source told People.
Daily Mail published photographs of Lopez and Affleck in a car together in Montana, with the "Good Will Hunting" actor driving. The publication reported that Affleck owns a home in Big Sky.
According to a source that spoke to E! News, Lopez and Affleck spent about a week in Yellowstone Club in Montana, "just the two of them."
Another source also told the publication that Affleck reached out to Lopez "to see how she was doing and they had dinner together a few times within this last month."
"They picked up where they last left off and are enjoying each other's company right now," the source said.
People went on to report that Lopez was in contact with the actor prior to her breakup with Rodriguez, but "it was friendly conversations" and she didn't meet up with Affleck until her relationship ended.
The publication also said that it was Affleck's idea for them to go on a trip outside of LA.
Amid dating speculation, Matt Damon, Affleck's longtime best friend and collaborator, weighed in and told the "Today" show: "I hope it's true. I love them both. I hope it's true. That would be awesome."
May 23, 2021: The stars spent time together in Miami.
They were photographed descending a staircase together and a source told E! News that Affleck "took a red-eye to Miami and went straight to J.Lo's new house in the early morning hours. She looked very happy to see him and they walked around the property together so she could show him around."
A source later told Us Weekly that they were full-on dating, though neither star commented on the reports.
"Jen and Ben are both very happy with each [other] and are excited to see where the relationship goes," an anonymous source told the publication. "They are full-on dating and very happy together."
According to Page Six, Lopez and Affleck "planned to announce their reunion in a more tightly controlled" prior to the initial photos circulated showing him reportedly visiting her house.
A source told Page Six that Lopez was originally "planning to make an announcement that they are back together on Instagram."
June 1, 2021: They were photographed with their arms around each other in California.
Days later, Affleck was photographed smiling at the paparazzi as he left Lopez's home in a vehicle.
In early June, Affleck was also seen spending time at a casino in Nevada with Lopez's mom, Guadalupe Rodríguez.
"They enjoy gambling together and have done it in the past," a source told E! News. "Ben had the opportunity to work in Vegas this week and she came out."
June 14, 2021: Photos obtained by Page Six showed Lopez and Affleck kissing.
Photos and a video published by the publication showed the two stars kissing, leaning in close, and talking with each other at a table.
According to Page Six, Lopez and Affleck were having dinner at Nobu in Malibu on Sunday. They were reportedly at the restaurant with Lopez's twins to celebrate the birthday of the "Hustler" star's sister, Lynda Lopez.
They continued to be photographed in public together.
In photos published by Page Six, they were seen at Universal Studios Hollywood on July 2 with their kids from previous relationships.
Not long after, Lopez liked a photo posted by a fan account on Instagram called @lopezaffleck, which showed Affleck on the set of the 2010 movie "The Town."
The "Argo" star was also photographed spending time at Universal CityWalk in Universal City, California with his kids and Lopez's daughter named Emme.
July 22, 2021: Leah Remini posted a photo of the couple in attendance at her 51st birthday celebration days prior.
A video recap shared by Remini included a photo of herself and Lopez hugging Affleck. Lopez also had her hand placed on the actor's chest as he posed in the middle.
July 24, 2021: Lopez made their rekindled relationship Instagram-official on her 52nd birthday.
"5 2 … what it do …💗 📸: @lacarba," she captioned the post. The final photo in Lopez's Instagram post showed her and Affleck kissing.
In addition, the couple celebrated Lopez's birthday with a party at L'Opera in St. Tropez, France. A video from the festivities showed Lopez singing along to her track "Jenny From the Block," whose music video starred Affleck, as waiters danced on the tables.
They were also seen seemingly recreating a famous moment from the "Jenny From the Block" music video, in which Affleck put his hand on Lopez's butt while on a yacht. Some fans have even speculated that the stars are recreating scenes for the music video's upcoming 20th anniversary next year.
Paparazzi photos that were taken of Lopez shortly after her birthday showed the singer wearing a gold necklace that spelled out "BEN."
After spending time in St. Tropez, the stars were seen dining at a restaurant in Capri, Italy and walking hand-in-hand.
August 23, 2021: Affleck was photographed browsing at Tiffany's in Century City, California.
Photos published by Page Six showed the actor shopping with his mother and his son.
An anonymous source told E! News that Affleck wasn't in search of an engagement ring for Lopez. instead, he was reportedly making a stop at the jewelry store as part of a scavenger hunt with his kids.
September 10, 2021: The couple returned to the red carpet for the first time since getting back together.
Lopez accompanied Affleck to the premiere of his upcoming film "The Last Duel" at the Venice Film Festival. The stars laughed, smiled, held hands, and kissed during their first red carpet appearance in 18 years.
September 13, 2021: Affleck and Lopez attended the Met Gala together.
Lopez walked the carpet solo in a Western-themed outfit from Ralph Lauren, but Affleck posed beside her for photos later at the event. They also kissed while wearing masks.
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