Ben Affleck-Jennifer Lopez Relationship Timeline: 20 Years On, How Bennifer Couldn't Make It Work

Bennifer reunion was the biggest headline of 2021, it took them 20 years and two engagements to get there. Now months after separation reports, Jennifer Lopez and Ben Affleck have finally confirmed they are parting ways. On Tuesday, August 20, JLo, 55, filed for divorce from Affleck, 52, ending their two-year marriage, as per a report in PEOPLE. The estranged couple has been living separately since April 26. Amid this, let's take a trip down memory lane and track JLo and Affleck's relationship history.

How did Jennifer Lopez and Ben Affleck meet?

JLo and Affleck met on the set of 2002 Gigli, the movie failed to draw the audience but sparks flew between the leading actors. At the time, the singer was still married to her second husband, Cris Judd. Soon after their divorce was finalised in July, she and Affleck went public with their relationship. In November 2002, Affleck proposed to Lopez as she met his family in Boston. The singer announced her engagement during an interview with Diane Sawyer saying, "It’s just a blanket, a quilt of rose petals, all over the whole entire house."

The engagement ring was made from a 6.1-carat pink diamond (her favourite colour at the time) by Harry Winston. It reportedly cost Affleck $2.5 million.

When Bennifer decided to postpone the wedding ceremony in 2003

Affleck and Lopez, who wooed their fans by walking the red carpet hand-in-hand for the premiere of Gigli, shocked the fans when a day before their wedding in September 2003 they announced their decision to postpone the ceremony. They released a joint statement that reads, "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."

Bennifer's separation in January 2004

Four months after postponing the wedding, Chicago Tribute reported that the couple had called quits. Later, Lopex's representative also confirmed in an official statement, "I am confirming the reports that Jennifer Lopez has ended her engagement to Ben Affleck. At this difficult time, we ask that you respect her privacy.”

Jennifer Lopez and Ben Affleck walked the separate paths

About six months after breaking up her engagement with Affleck, Loez married Marc Anthony, a Latin music star, on June 5, 2004. Four years later, the couple welcomed twins Emme and Max in 2008, but three years later, they separated and, then divorced in 2014.

Ben Affleck married Jennifer Garner in June 2005

During that time, Affleck had started dating Jennifer Garner, whom he met on the set of Pearl Harbor. But they became close friends while filming 2003's Daredevil. The couple started dating in August 2004 and a year later on June 29, they exchanged vows in a private Turks and Caicos ceremony. The same year in December, the couple welcomed their first child, a daughter, Violet, followed by their second daughter Fin in January 2009 and a son Samuel in February 2012. In June 2015, Affleck and Garner publicly announced their separation and jointly filed for divorce in 2017.

Bennifer rekindled their love in 2021

Since the beginning of 2021, rumours have been rife that Lopez and Affleck are back together. They were often snapped together at dinners and parties. In May 2021, US Weekly reported that they jetted off to Montana on a vacation and, they "looked very happy together". It was only in July 2021, Lopez hinted at getting back with Affleck during an interview with Zane Lowe on Apple Music 1. During the interview, she shared how great she'd been doing as something was “happening again”.

Ben Affleck and Jennifer Lopez went red-carpet official in September 2021

After months of speculation, the couple made a big revelation during the 2021 Venice Film Festival's premiere of The Last Duel, when they walked hand-in-hand on the red carpet. Later that month, they were also snapped kissing each other inside the venue of the Met Gala. Their relationship revelation was followed by several memorable events, including Lopez bringing her twins to Los Angeles to join Affleck for the Thanksgiving holiday.

Inside Bennifer's second engagement in April 2022

A year later in April 2022, the couple took their relationship to the next level again and exchanged rings in a private ceremony. The singer confirmed the news to PEOPLE and shared the relationship status on her  On the JLo newsletter, teasing it with a video on Twitter. "Major announcement!!!! OnTheJLo.com,” she wrote, including a diamond ring emoticon in her bio.

Finally! Bennifer got married in July 2022

It was on July 16 when the couple obtained a marriage license in Clark County, NV, according to TMZ and were officialy married. Following their hush-hush wedding, the couple jetted off to Paris with their kids for a honeymoon/work trip. However, on August 21, the couple had an intimate wedding in Las Vegas and several images and videos from their dreamy white wedding went viral on the internet.

A year later on August 21, Lopez shared a set of two photos from her wedding album and penned a sweet note for Affleck. The caption read, “One year ago today… Dear Ben, Sitting here alone, Looking at my ring ring, Feeling overwhelmed, It makes me wanna sing sing, How did we end up here, Without a rewind, Oh my, This is my life…”

Separation rumours began to swirl in May 2024

Everything was going fine until in May this year, Affleck was snapped leaving his house in Brentwood, California, alone, while Lopez was snapped house hunting alone. It was hard to believe for Bennifer fans as on March 16 they were snapped together with the actor's 12-year-old son Samuel to watch the Los Angeles Lakers play the Golden State Warriors. They were seated together holding hands and were seen enjoying the game to the fullest. To be noted, according to Lopez's divorce filing documents, the couple separated on April 26.

However, neither Lopez nor Affleck confirmed the rumours and continued to live separately. Amid the separation rumours, on Father's Day in June, JLo dropped a photo of Affleck on her Instagram Stories calling him the family's "hero".

Recalling the events that hinted Jennifer Lopez and Ben Affleck's separation

Many events fueled Bennifer's separation starting from June when Ben Affleck put their marital home for sale. This was followed by the actor purchasing a $20.5 million home in LA. In July, the estranged couple celebrated the national holiday on opposite sides of the country, with Lopez, along with kids, vacationing in the Hamptons and Affleck in Los Angeles. Not just this, the Batman actor also skipped JLo's 55th birthday bash in the Hamptons and even passed on the vents such as the Met Gala and the premiere of JLo's film Atlas.

Earlier this month (August), JLo was snapped house hunting to reportedly start a fresh life. This came days after Affleck had bought a new estate in Los Angeles. A source told People that Lopez “hasn’t seen Ben for weeks. They’re moving on separately. Jennifer is trying to find a new home to start fresh."

After spending quality time with her and Affleck's kids, JLo, on August 20, filed for divorce in Los Angeles Superior Court.