Bennifer was the It couple of the early aughts. Though the two ultimately went their separate ways in 2004, a recent vacation to Montana might indicate the resurrection of one of Hollywood’s favorite romances.
Ahead, we take a stroll down memory lane and track Ben and Jen’s relationship history, from how they met to the stunning pink diamond that Affleck proposed with and beyond.
2001: They meet.
The then rising Hollywood actors first met on the set of Gigli, a rom-com that released in 2003. The movie ultimately flopped, but sparks flew between the leading costars.
At the time, J.Lo was still married to her second husband, dancer Cris Judd; she and Affleck went public with their relationship soon after her divorce from Judd. (Their divorce was finalized in 2003.)
In 2016, the actress reflected on the beginning of their relationship in an interview with People. “We didn’t try to have a public relationship,” she said. “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 also revealed her first impression of Affleck. “I felt like … ‘Okay, this is it,'” she said. “[But] sometimes I feel like what you think people are and how you see them when you love them is different than when they reveal later.”
Related article: J.Lo Goes Instagram-Official With Ben Affleck On Her 52nd Birthday
2002: Ben makes a cameo in “Jenny from the Block.”
The now iconic music video features a steamy moment from Bennifer. With J.Lo in a hot-pink bikini and Affleck in a white tank, the lovebirds sunbathe on a boat while the Good Will Hunting actor lovingly displays some PDA with J.Lo’s bottom. The video also had a tongue-in-cheek reference to the tabloids’ obsession with their relationship, including surveillance camera footage and pap photos of the two.
In 2010, J.Lo spoke of the pressures that the media put on their relationship during a guest appearance on The Graham Norton Show. “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. … Our relationship, I think, did suffer because of that. That’s not the only reason … but I think it definitely played a part in the dynamic of our relationship.”
November 2002: They get engaged.
J.Lo confirmed the happy news in an interview with Diane Sawyer. “It’s the most magnificent thing I’ve ever seen,” she said of the 6.1-carat pink diamond from Harry Winston that Affleck gave her. The rock reportedly cost Affleck $2.5 million.
Related article: A Bennifer Reunion Is the Love Story We Deserve
2003: They star in another movie together.
J.Lo played the dead wife of Affleck’s character in Jersey Girl, a dramedy that was slated for a 2003 release, but got pushed to the following year. Also starring Liv Tyler, the film ultimately underperformed at the box office, grossing only $36 million.
September 2003: They postpone their wedding.
Days before the two were set to officially tie the knot, they released a joint statement announcing the ceremony’s postponement.
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.
January 2004: Bennifer is over.
On January 22, 2004, the two ended their engagement. J.Lo confirmed the sad news through her spokesperson.
“I am confirming the report that Jennifer Lopez has ended her engagement to Ben Affleck,” the statement said at the time, per MTV. “At this difficult time, we ask that you respect her privacy.”
June 2004: J.Lo moves on.
In June of 2004, the “Let’s Get Loud” singer married singer-songwriter and longtime friend Marc Anthony. The two welcomed twins, daughter Emme Muñiz and son Max Muñiz, in 2008. They separated in 2014.
In her 2014 book, True Love, J.Lo reflected on the turbulent period between announcing her split from Affleck and marrying Anthony. “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. “I sought out comfort in another person, tried to find someone who could make me feel loved and wanted in my loneliest hour. … Marc came back into my life three days after I should have been at the altar saying ‘I do’ to another man.”
Related article: Both Ben Affleck And Marc Anthony Still Have Major Love For J.Lo
She added that their romance may have been her attempt at a quick fix for her heartbreak. “Thinking back, maybe deep down I knew that this was a Band-Aid on the cut, that my wound hadn’t been stitched or healed,” she wrote. “But I pushed all that to the back of my mind. Because life takes unpredictable twists and turns, right? And you’ve just got to go with what you feel is best in the moment.”
2005: Ben marries Jennifer Garner.
Affleck, too, soon moved on. He married Garner in 2005, and the new Hollywood couple welcomed three children together over the years: daughters Violet and Seraphina Affleck, and son Samuel Affleck. The couple divorced in 2018.
April 2021: Bennifer reunites.
After J.Lo ended her engagement to Alex Rodriguez and Affleck split from Ana de Armas, the two were spotted hanging out again. Page Six reported on April 30 that the actor was photographed visiting her Los Angeles home multiple times.
“Security picks him up at a nearby location and drops him off after spending a few hours at her house,” said a source, who insisted on the platonic nature of Affleck’s visits. “They are friends,” the insider continued, “they’ve never not been.”
May 2021: J.Lo and Ben jet off to Montana together.
Nearly two decades after they called it quits, Lopez and Affleck departed for a weeklong vacation to Montana. This is reportedly following their appearances together at Lopez’s L.A. mansion the day of their departure in addition to Global Citizen’s Vax Live benefit concert, per People.
An insider confirmed the getaway to E! News.
“They really care for each other and they picked up right where they left off,” a source told E!
“[Jennifer] spent several days with Ben out of town,” another source added. “They have a strong connection. It’s all been quick and intense, but Jennifer is happy.”
“They have been in touch here and there throughout the years,” said an additional insider close to the singer. “Ben reached out to her to see how she was doing and they had dinner together a few times within this last month. It’s natural between them and the chemistry is unreal. They picked up where they last left off and are enjoying each other’s company right now.”
May 2021: Both Lopez and Affleck “seem committed” to each other.
People reported that Lopez and Affleck are determined not to let distance affect their reunion and that Lopez seems to be in a good place following her recent split from Alex Rodriguez. “Jennifer is doing well. She seems very happy and excited about her future,” a source told the outlet.
According to People, the singer flew out to Los Angeles to spend more time with her former fiancé. “Jennifer was just in Los Angeles for a couple of days,” said the source. “She spent time with Ben. They have kept in touch every day since their Montana trip… It’s a tricky situation since they live so far from each other, but they both seem committed to making things work.”
Weeks later, Affleck also reportedly took a flight to J.Lo’s residence in Miami to spend more cozy, quality time with the actress. A separate source told E! that Affleck’s demonstrated investment toward their rekindling romance amid both stars’ work obligations and coastal commutes has been nothing short of impressive to Lopez, even adding that such efforts by Affleck have made her feel “giddy.”
“It’s comforting to her and she is smitten,” said the insider. “They are giddy together and you can tell she’s really happy.”
“Ben has been making the effort to make it work with their schedules. He’s really making a huge effort,” the source also added. “J.Lo thinks Ben has really stepped up and loves this version of him.”
Related article: Jennifer Lopez and Ben Affleck Reportedly Are “Madly in Love”
June 2021: The pair are reportedly already thinking about their future.
Lopez and Affleck are reportedly in it for the long haul. Per People, Bennifer are “slowly starting to talk about the future.”
“This is not a casual relationship,” a source said. “They are taking it seriously and want it to be long-lasting.”
The pair are also determined to make the long distance work. Affleck is currently based in Los Angeles, while Lopez often works out of Miami.
“They will continue to travel back and forth between Los Angeles and Miami,” the source shared. “They are very happy together.
June 2021: The pair are “hopeful” their relationship will work this time around.
According to Entertainment Tonight, Lopez and Affleck are feeling positive about their choice to romantically reunite.
“J.Lo and Ben are very much a couple and have been telling friends that they’re together,” a source told the outlet. “When they first reconnected, they had to see if the spark was still there because it had been a while. It was, so now they are both fully in it.”
Apparently, the two have also talked through their past.
“[They] talked about the past and why things didn’t work out,” the sourced said. “They are both hopeful about their relationship this time around and putting the effort in. They have both matured and are on the same page and it has been easy.”
Unlike Lopez’s previous relationship with Rodriguez, this time around, the superstar is opting to keep her professional and personal life separate.
“J.Lo and A-Rod were always investing together and mixing business with their relationship and Ben is less into that,” the source added. “They are just genuinely enjoying each other’s company and having a great time. Jen is very supportive of Ben and his career, but she is also connected, successful and has her own life.”
July 2021: Their families are getting along “great.”
Lopez’s and Affleck’s families are beginning to bond more, according to E! News. Following weeks of rendezvouses between the pair, Affleck finally joined Lopez and her children at a family birthday party and the two brought their kids together for a trip to Universal Studios. Over the July 4 weekend, Affleck also joined Lopez and her teenaged twins for some “low-key” time at her Hamptons home.
“J.Lo and Ben seemed to enjoy being on the east coast and spending time at her beautiful home,” a source told E! News. “It was a nice change of scene for them and a great time with friends and family.”
Related article: J.Lo And Ben Affleck Are Already House Hunting Together
July 2021: Ben and Jennifer may be moving in together soon.
Bennifer are moving full speed ahead in their romance. According to Entertainment Tonight, close friends of the pair said that they “wouldn’t be surprised” if the rekindled power couple “move in together and ultimately end up together.”
“They’re spending all of their free time together and making each other a priority. J.Lo falls hard and has certainly done the same with Ben again this time around,” a source told ET. “Ben is a guy’s guy and does his own thing, which J.Lo loves. He has his own life and is famous in a different way than she is and is not trying to compete with her by any means. They just support and love each other.”
August 2021: Ben browses engagement rings with his mom and son.
In photographs obtained by Page Six, Affleck was seen glancing at engagement rings while popping by a Tiffany & Co. jewelry store at a local shopping mall. Affleck was joined by his son, Samuel Affleck, and his mother, Chris Boldt, for the shopping excursion. The actor’s outing comes after spending more time not just with Lopez, but their children, too, as they slowly work to blend their families.
“Since Jennifer and Ben are in it for the long run, it’s just a natural step that they all spend time together with the kids,” a source told People.
This article originally appeared on Harper’s BAZAAR US.