Jennifer Lopez and Ben Affleck have been spotted spending time together as of late following her split from fiancé Alex Rodriguez

By Ashley Boucher
Updated May 10, 2021 01:45 PM
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While they haven't been an official couple for nearly two decades, Jennifer Lopez and Ben Affleck are certainly sparking reconciliation rumors.

The pair, who dated from 2002 to early 2004, recently reconnected in Los Angeles following Lopez's split from Alex Rodriguez last month.

Since then, they have also been spotted together in Montana, having "spent several days" together in the state, a source recently told PEOPLE.

Here's a look back on Bennifer's relationship timeline.

How It All Began

Lopez, 51, and Affleck, 48, met in 2002 on the set of the movie Gigli, which came out the following year. At the time, Lopez was married to her second husband, Cris Judd. They divorced in 2003, and Lopez and Affleck went public with their romance shortly after.

Lopez told PEOPLE in 2016 that when she first met Affleck, she "felt like … 'Okay, this is it.' "

The duo quickly became one of the most popular celebrity couples and one of the first duos to receive a hybrid Hollywood name: "Bennifer."

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Ben Affleck, Jennifer Lopez
| Credit: getty

Ben's Proposal

In a November 2002 interview with Diane Sawyer, Lopez revealed her engagement to Affleck, describing it as "traditional, but also in a very spectacular way, as of course Ben would do it … it was very, very beautiful."

PEOPLE reported at the time that Affleck proposed with a custom-made Harry Winston pink-diamond solitaire ring he chose himself.

In her interview with Sawyer, 75, Lopez described her then-fiancé as "brilliantly smart … Loving. Charming. Affectionate," adding that her mother approved.

"And I just admire him in every way," she said.

jennifer lopez and ben affleck
Jennifer Lopez, Ben Affleck
| Credit: getty

She also acknowledged that some people viewed their relationship as unlikely, but pointed out that she and the actor had bonded over similar upbringings.

"We've talked about this so many times, and we talked about how people kind of see him with … one type of person and me with another type of person, and the two of us together is like, 'How did that happen?' " she said.

Lopez added, "And how we're probably more alike and from the same kind of background … same kind of upbringing and same kind of family and same kind of house."

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Ben Affleck and Jennifer Lopez in 2002
| Credit: getty

Tabloid Frenzy

Heading into 2003, Lopez and Affleck were the most popular Hollywood couple to appear in the tabloids. famously hounded by the paparazzi and constantly featured in the media.

Lopez even used their notoriety in the music video for her song "Jenny from the Block," which featured paparazzi shots of herself and Affleck doing everything from pumping gas to lounging on a yacht together.

"We didn't try to have a public relationship," Lopez told PEOPLE in 2016. "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."

jennifer lopez and ben affleck
Jennifer Lopez and Ben Affleck in 2002
| Credit: getty

Lopez recently told InStyle that the media circus surrounding her relationship with Affleck was "just crazy."

"Now at least I can show you who I am a little bit," she said. "Back then you just believed anything you read on the cover of a tabloid. Many times it wasn't true, or it was like a third of the truth."

In a January podcast interview, Affleck reflected on how rude media coverage of Lopez was when they were together.

"People were so f---- mean about her — sexist, racist. Ugly, vicious s--- was written about her in ways that if you wrote it now you would literally be fired for saying those things you said," he said. "Now it's like, she's lionized and respected for the work she did, where she came from, what she accomplished — as well she f----- should be! I would say you have a better shot, coming from the Bronx, of ending up as like [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."

The Breakup

The pair were set to tie the knot in Santa Barbara in September 2003, but postponed the ceremony just one day before their scheduled date.

"Due to the excessive media attention surrounding our wedding, we have decided to postpone the date," they said in a statement at the time. "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," the statement continued. "We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends."

jennifer lopez and ben affleck
Jennifer Lopez, Ben Affleck
| Credit: getty

PEOPLE previously reported that after briefly splitting up in the wake of the canceled wedding, the duo rekindled their relationship — but officially called it quits in January 2004. The intense media attention is largely said to have been a major factor in their breakup.

"Jennifer Lopez has ended her engagement to Ben Affleck. At this difficult time, we ask that you respect her privacy," Lopez's rep said at the time, while Affleck's rep said, "I am not going to confirm anything about his personal life. We don't want to get dragged into quicksand. Everybody wants a war. It's not happening from our side."

In her interview with PEOPLE in 2016, Lopez said that despite the split, there was "genuine love" between herself and Affleck.

"I think different time different thing, who knows what could've happened, but there was a genuine love there," she said.

Moving on

Both Lopez and Affleck went on to get married and have children. Lopez married Marc Anthony in 2004 and welcomed twins Max and Emme in 2008.

Affleck married Jennifer Garner in 2005 and shares son Samuel and daughters Seraphina and Violet with the actress. They divorced in 2018.

Lopez and Anthony divorced in 2014. She dated Rodriguez for four years before they broke off their engagement earlier this month.

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Ben Affleck (L); Jennifer Lopez
| Credit: Christopher Smith/invision/AP/shutterstock; emma mcyntire/getty

Friendly Exes

Lopez and Affleck have remained supportive of one another in the years following their split.

Last year, Affleck showed his support for Lopez's acting career, saying that she should have been nominated for an Oscar for her role in Hustlers.

"She should have been nominated. She's the real thing," Affleck told New York Times reporter Brooks Barnes. "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—— baller."

Reconnecting

The exes have been spending time together following Lopez's split from Rodriguez, and Affleck visited Lopez at her L.A. home on April 30, a source told PEOPLE.

"They are friends. They have always been friends and they have seen each other through the years," another source said. Affleck was also photographed leaving a white Escalade SUV that allegedly belongs to Lopez, according to the New York Post's Page Six.

After Affleck was spotted leaving Lopez's L.A. home, a source told PEOPLE the two remain the friendliest of exes 17 years after their split. 

"They have a great time hanging out. ... It's been years since they caught up properly. They have lots to talk about," the insider said. "said the insider. "They plan on hanging out again."

Jennifer Lopez, Ben Affleck, NO REUSE, NO SYNDICATION
Jennifer Lopez and Ben Affleck on April 29
| Credit: BACKGRID (2)

Less than a week later, the two were spotted in Montana together. Sources told PEOPLE they were pictured riding in a car together near a resort in Big Sky, where Affleck has a home. He was seen behind the wheel with Jennifer in the passenger seat.

"[Jennifer] spent several days with Ben out of town. They have a strong connection. It's all been quick and intense, but Jennifer is happy," an insider told PEOPLE of the pair who were later spotted arriving back in L.A. Saturday on a private jet.

Prior to the Montana sighting, Lopez and Affleck both attended and participated in the VAX LIVE: The Concert to Reunite the World event, which aired Saturday and at which Lopez performed. (They were not pictured together at the Los Angeles venue.)