Close to two decades after they started seeing each other, got engaged and called off their wedding just days before walking down the aisle, actor Ben Affleck and pop icon Jennifer Lopez have reportedly got back together, and even took off to Montana for a vacation recently. This, days after JLo called off her high-profile engagement with former baseball star Alex Rodriguez and Ben broke up with actor Ana de Armas. Nothing makes the Internet gleefully rub its hands as much as Noughties nostalgia (remember how we keep willing Brad Pitt and Jennifer Aniston to get back together). t2 traces the timeline of one of the most talked-about celebrity relationships which may well be on rekindling route...

YEAR 2001

A still from Gigli, their first film together

Exactly two decades ago, Jennifer Lopez, then 32, and Ben Affleck, then 29, met on the sets of their film Gigli, which released in 2003. At that time, JLo was still married to her second husband Cris Judd. Sparks flew between Jen and Ben and after she divorced Judd, the two went public with their relationship.

Gigli, however, wasn’t as lucky. The film was a resounding flop on release and one of the worst reviewed films ever and even today, Google throws up numerous search results (all uncomplimentary) for the question, ‘Was Gigli such a bad film?’

In a 2016 interview, JLo reflected on her first impression of Affleck saying, “I felt like … ‘Okay, this is it’. 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.”

YEAR 2002

Their steamy appearance in the music video for JLo’s Jenny On The Block

With their relationship coming in for huge public attention, the couple were the first to be given a ship name — Bennifer. With the paparazzi recording every breath they took and every move they made, Bennifer eclipsed all other celebrity couples of the time to feature on the cover of glossies almost every other day.

That year, Ben made a steamy appearance in JLo’s now iconic music video Jenny On The Block. With Jen in a hot-pink bikini and Ben in a white vest, the lovebirds are shown sunbathing on a boat and moving on to show some PDA. The video had a tongue-in-cheek reference to the tabloids’ obsession with their relationship, including surveillance camera footage and pap photos.

NOVEMBER 2002

JLo flaunts her engagement ring on the red carpet

Bennifer announced they were engaged, with JLo publicly sporting a custom-made Harry Winston six-carat pink diamond ring that reportedly set Affleck back by $2.5 million. “It’s the most magnificent thing I’ve ever seen,” JLo had said at that time. Such was the interest around their engagement (and the ring) that the singer later revealed that even Barbra Streisand “ambushed” her at a party, wanting to take a closer look at the ring.

YEAR 2003

Jen and Ben in Jersey Girl, their second film together

The two starred in another film together, but it was only a special appearance in Jersey Girl for Jennifer, who starred as the dead wife of Ben’s character. Jersey Girl, also starring Liv Tyler, underperformed at the box office. But the public interest around Bennifer continued to rise.

SEPTEMBER 2003

The couple at a basketball game just days before pushing back their wedding

The couple continued to make appearances, and even announced a wedding date. But days before the ceremony, they issued a joint statement announcing that they had decided to postpone their wedding.

The statement read: ‘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 realised 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

Three months after postponing their wedding, the couple inexplicably split, with Jennifer issuing a statement through her spokesperson that read, “I am confirming the report that Jennifer Lopez has ended her engagement to Ben Affleck. At this difficult time, we ask that you respect her privacy.”

Six years later, the singer, while being a guest on The Graham Norton Show, spoke about the pressure that the constant public attention put on their relationship. “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. 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.

JUNE 2004

Ben Affleck with Jennifer Garner

Possibly on the rebound, JLo suddenly got married to longtime friend and singer Marc Anthony. The couple, who have twins Emme and Max together, separated after 10 years of marriage. Ben went on to marry actor Jennifer Garner in 2005 and had three children with her. They divorced in 2018, amid rumours that he had been serially cheating on her.

Affleck and JLo, however, continued to be friends through the years. In her 2014 memoir True Love, the popstar fondly looked back at the relationship. “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. “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.” She also added that her relationship with Affleck, “self-destructed in front of the entire world”.

Jennifer Lopez and Marc Anthony

Admitting that her marriage to Marc was a quick fix to get over her heartbreak, she wrote: “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. 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.”

Ben, who hasn’t been as vocal on the split, did, however, open up on an occasion or two to say, “I think Jen and I made a mistake in that we fell in love, we were excited and maybe too accessible. I don’t think either of us anticipated the degree to which it would take on a world of its own.”

APRIL 2021

Thrust firmly into the spotlight after ending her relationship of many years with Alex Rodriguez, JLo reportedly sought comfort in Affleck, who she had been in touch with through the years. “They have been in touch here and there throughout the years,” a source close to the singer told E! “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. They are friends. They’ve never not been.”

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,” revealed a source.

MAY 2021

The two were clicked holidaying together in Montana recently

What now seems to be a rekindled relationship was confirmed by the fact that the two jetted off for a week-long vacation to Montana recently. This was after they made a joint appearance at Global Citizen’s Vax Live benefit concert. “[Jennifer] spent several days with Ben out of town,” a source said. “They have a strong connection. She wants to give it a shot with Ben. They never really had closure and she has always wondered what could have been. It’s all been quick and intense, but Jennifer is happy.”

Images sourced by the correspondent