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A timeline of Jennifer Lopez and Ben Affleck’s complicated relationship

With Bennifer 2.0 in full swing, Page Six is breaking down the complete timeline of Ben Affleck and Jennifer Lopez’s complicated relationship: How it started, why it ended and what’s in store for them now.

Where it all started

Jennifer Lopez and Ben Affleck attending the “Gigli” premiere in 2003. Corbis via Getty Images

Lopez first met Affleck in 2001 on the set of their movie “Gigli.” Though the film was a critical and box-office failure upon its 2003 release, the couple’s off-screen chemistry wound up a hit.

Lopez was still married to her second husband Cris Judd at the time, but that didn’t stop romance rumors from bubbling up.

They’re getting warmer

The duo starred in “Jersey Girl” together in 2002. Getty Images

Despite the drubbing “Gigli” took, Ben and Jen filmed their second movie together, “Jersey Girl” — in which Lopez played Affleck’s character’s wife (who, incidentally, died onscreen immediately) — from September to December 2002. This collaboration, however brief, notably occurred after …

J.Lo becomes available

Lopez and Cris Judd, seen here in 2001, ended their marriage in 2003. Getty Images

J.Lo legitimized her romantic relationship with Affleck when things went south in her marriage to Judd.

She and the choreographer got married in September 2001, but things were rocky for the couple throughout their relationship and they called it off in June 2002, finalizing their divorce in 2003.

Bennifer is born

Ben and Jen are seen at a movie premiere in 2002 WireImage

One of Bennifer’s most iconic moments came early, in Lopez’s unforgettable music video for “Jenny from the Block,” which premiered on MTV in November 2002, after being filmed in October of that year.

The same month the clip came out, Affleck proposed to J.Lo, popping the question with a 6.1-carat pink diamond by Harry Winston that reportedly cost $2.5 million.

Lopez initially revealed the happy news during an interview with Diane Sawyer, calling the proposal “traditional, but also in a very spectacular way, as of course, Ben would do it.”

She added that Affleck was “brilliantly smart, loving, charming, and affectionate.”

And of the massive rock, she shared, “It’s the most magnificent thing I’ve ever seen.” 

Massive rock rocks relationship

The couple are seen on a red carpet in 2003 Getty Images

While things heated up quickly for the pair, Lopez and Affleck decided to postpone their 2003 wedding.

“Due to the excessive media attention surrounding our wedding, we have decided to postpone the date,” the couple said in a joint 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.”

Bennifer no more

Jennifer Lopez and Ben Affleck attending the Academy Awards in March 2003. Getty Images

Calling off their engagement was a clear sign that things weren’t going well for the couple following the hot ‘n’ heavy early days of their romance.

In 2004, Lopez and Affleck revealed that they were officially calling off their engagement and ending their relationship.

“Jennifer Lopez has ended her engagement to Ben Affleck. At this difficult time, we ask that you respect her privacy,” a rep tersely told People at the time.

“I am not going to confirm anything about his personal life,” Affleck’s rep added. “We don’t want to get dragged into quicksand. Everybody wants a war. It’s not happening from our side.”

Living their separate lives

Jennifer Lopez is seen with Marc Anthony in 2011 (L) and Ben Affleck in photographed with Jennifer Garner in 2013.

Both stars moved on to other relationships fairly quickly, tying the knot with other celebs around the same time.

Lopez went on to marry Marc Anthony in June 2004, with whom she had two children: twins Emme and Max, born in 2008.

Meanwhile, Affleck tied the knot with Jennifer Garner in June 2005 and went on to welcome three kids with the actress: Violet, Seraphina, and Sam.

AffGar would last slightly longer than AnthoPez, however, with the Latin music superstars splitting in 2014 and the big-screen couple following suit in 2018.

The J-Rod saga starts … and ends

Lopez and Rodriguez, seen here in 2020, eventually called off their engagement. WireImage

Lopez entered into another whirlwind romance with Alex Rodriguez in 2017, moving into a $15 million love nest with him after a year of dating.

Then in 2019, the pair announced that they were officially engaged.

But Lopez called off their engagement after rumors swirled that Rodriguez had been up to no good with “Southern Charm” star Madison LeCroy.

In March 2021, Page Six exclusively reported that their engagement was off, and nearly a month later they confirmed that they had ended things for good.

Meanwhile, Affleck was linked to a slew of women during J-Rod’s run, including “Knives Out” star Ana De Armas until January 2021.

Sparks fly for Bennifer again

Affleck and Lopez, seen here in 2003, still had respect for each other years later. Getty Images

While the duo went their separate ways and started families, they still seemingly remained on good terms.

Affleck praised Lopez’s work ethic in April 2021, telling InStyle, “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.”

A 2000s throwback

Lopez peeped in on Affleck while they vacationed in Miami together in May 2021 MEGA / BACKGRID

Affleck and Lopez took the world by storm when they were first spotted hanging out together again in LA in April 2021 and in Montana the following month.

Things continued to heat up for the duo and they were soon after spotted on a romantic getaway in Miami.

And in June, we reported that their PDA left little doubt that the pair were fully back together again after photos of Ben and Jen getting cozy on a date surfaced.

Taking things slow

They made the rounds in Miami together. MiamiPIXX / VEM / BACKGRID

While it looked like Lopez and Affleck jumped back into their relationship with lightning speed, their rekindling may have been coming for quite some time, as Affleck reportedly sent love letters to J.Lo prior to her breakup from Rodriguez.

That romantic streak seems to have carried over into the second act of the couple, who were “very affectionate” during a June dinner date in West Hollywood.

But as Page Six reported in June, while things are getting serious for the couple, Lopez’s children remain her first priority.

Meet the kids

The pair introduced their respective kids to each other. Getty; jlo/Instagram

The couple decided to introduce their respective children to each other as they got more and more serious.

In June 2021, Affleck was spotted chatting with J.Lo’s two kids whom she shares with ex-husband Marc Anthony: Max and Emme.

And that August, Affleck brought his three kids — daughters Violet, Seraphina, and son Samuel — to tag along with J.Lo and her twins to see “Hamilton” in LA.

Going public

They made their red carpet debut at the Venice Film Festival in September 2022. Getty Images

As they started to mesh their families together, the stars decided it was time they went public with their love.

In July 2021, Lopez made their love Instagram-official by posting a PDA-filled photo of the pair to her social media page in honor of her 52nd birthday.

And they made their red carpet debut at the Venice Film Festival in September last year.

Wedding bells are ringing

Affleck popped the question with a green engagement ring. Getty; OnTheJlo.com

Lopez and Affleck continued to date seriously for months, but in April 2022, rumors swirled that the pair were heading down the aisle.

The singer was spotted wearing a massive ring on her left ring finger, sparking speculation that Affleck had popped the question.

The next day, the pair confirmed that they were engaged for the second time, announcing the happy news in a short video via her fan newsletter, On The JLo, where she showed off her green ring.

The ring, which appears to be adorned with a very rare green diamond, could be valued at well over $5 million and could be worth more than $10 million,” Page Six Style reported at the time.

Tying the knot

Affleck wore a white tuxedo jacket while J.Lo wore a dress “from an old movie.” "On The JLo" Newsletter.

Lopez and Affleck officially confirmed they said “I do” in the July 17 edition of her “On The JLo” newsletter.

“We did it. Love is beautiful. Love is kind. And it turns out love is patient. Twenty years patient,” the “Marry Me” actress wrote in the post.

She called the Las Vegas ceremony “exactly what we wanted,” as she detailed their trip down the aisle.

“Last night we flew to Vegas, stood in line for a license with four other couples, all making the same journey to the wedding capital of the world. Behind us two men held hands and held each other. In front of us, a young couple who made the three hour drive from Victorville on their daughter’s second birthday—all of us wanting the same thing— for the world to recognize us as partners and to declare our love to the world through the ancient and nearly universal symbol of marriage,” she continued.

The Super Bowl halftime performer also noted that she wore “a dress from an old movie” as they exchanged vows in the “little chapel” and “gave one another the rings we’ll wear for the rest of our lives.”

The pair tied the knot again in front of friends and family in a lavish ceremony at Affleck’s 87-acre Georgia estate in August.