Jennifer Lopez and Ben Affleck: A Relationship Timeline

Romance rekindled! Ben Affleck and Jennifer Lopez, were seen together in Miami on Sunday, May 23 — two weeks after their trip to Montana (more on that later). The formerly engaged couple have seemingly rekindled their romance nearly two decades later, and were spotted walking down the stairs of a Miami area home as they appeared to be enjoying the South Beach weather. Could this pair finally be getting things right the second time around? Keep reading for photos of the two over the years, a relationship timeline, and more shots from their weekend in Miami.

In this photo, Jennifer Lopez and Ben Affleck are seen at a pre-game ceremony for the Boston Red Sox and New York Yankees on Oct. 11, 2003. Jennifer, then 34, was all smiles as she stood next to Ben, then 31. The couple, better known as 'Bennifer,' were once one of Hollywood’s most iconic couples. The romance began after the pair met on the set of their film ‘Gigli’ in 2002. After a whirlwind romance, Ben popped the question at his mother’s Boston home with an unforgettable 6.10 carat pink diamond ring from legendary jeweler Harry Winston, which reportedly cost about $1.2 million. Jennifer confirmed the engagement during an ABC interview with Diane Sawyer. 

The pair were regularly photographed throughout their romance, including on a trip to Paris and at the Academy Awards — but sadly split just four days before their wedding in Jan. 2004. However, they’ve been on good terms in 2021, with Ben shouting out Jen’s work ethic in an article with InStyle magazine. As of April, it appears that the pair have reunited following Jen’s split from Alex Rodriguez. 

Keep scrolling for a timeline of their romance! 

Jennifer Lopez was still married to her second husband, Cris Judd, when she met Ben Affleck on the set of ‘Gigli’ in 2002. However, she and Cris split in the middle of that year, and she started dating Ben shortly afterward. Here, the two are photographed on the set of one of J.Lo’s music videos in 2002. They shared an intimate meal over at a romantic table for two, and at one point, Ben leaned in to give Jen a kiss.

Jennifer Lopez and Ben Affleck are photographed on the set of her 2002 music video for ‘Jenny From The Block.’ Ben famously co-starred in the video with her at the height of their romance. 

Related: Jennifer Lopez’s Hottest Performance Looks Of All Time

Ben Affleck, Jennifer Lopez and Nicole Kidman are seen at the opening of her restaurant Madres in Pasadena, California in April 2002. Jennifer’s restaurant served Latin food.

It didn’t take long for Jen and Ben to take their relationship to the next level. In Nov. 2002, Ben proposed, and Jennifer accepted. Just weeks later, he was by her side at the premiere of her movie ‘Maid in Manhattan’ on Dec. 8, 2002. The pair held hands as they headed into the event, and Jennifer looked stunning in a white dress.

Related: Jennifer Lopez’s Engagement Rings In Photos: Her Pink Diamond From Ben Affleck & More

Jennifer Lopez and Ben Affleck are seen at the premiere of her romantic comedy ‘Maid in Manhattan’ on Dec. 8, 2002 in New York City. The film remains one of her most known to date.

"[The proposal] was traditional, but also in a very spectacular way, as, of course, Ben would do it," Jennifer said, regarding their engagement. "It was very, very beautiful."

Ben Affleck and Jennifer Lopez are seen attending the premiere of his film ‘Daredevil’ in Feb. 2003. J.Lo stunned in a Pucci dress for the occasion.

Related: Jennifer Lopez Through The Years: See Her Transformation

The two attended so many red carpets together throughout their relationship. Here, they cozy up while appearing at the ‘Vanity Fair’ Oscars Party in March 2003. It’s one of the most high-profile events of the year, and all eyes were definitely on Ben and Jen in 2003.

While inside the bash, Jennifer and Ben were not shy about packing on the PDA — even in the A-list-filled room! At one point, she was nearly sprawled across his lap as they leaned in close to share a special moment.

In 2002 and 2003, Jen and Ben filmed another movie together. They both starred in the flick ‘Jersey Girl,’ which wasn’t released until the following year (March 2004). Here, they appear in a still from the movie with their on-screen daughter.

Related: Jennifer Lopez’s Hottest Latin Grammy Awards Looks Of All-Time

Jennifer Lopez and Ben Affleck’s chemistry was definitely evident as they appeared in the film. In this scene, they wrapped their arms around each other and leaned in for a kiss on-screen.

Ben Affleck and Jennifer Lopez are seen filming ‘Jersey Girl’ in Nov. 2002 while in NYC. For the chilly scene, they bundled up in coats as they walked down the sidewalk.

Jennifer Lopez & Ben Affleck were hot and heavy by the time their movie, ‘Gigli’, came out in July 2003. At the premiere, they coupled up for photos on the red carpet. Jennifer looked incredible in her plunging black dress, while Ben was dapper in his suit and blue shirt

Ben Affleck and Jennifer Lopez are seen in a still from their film ‘Gigli,’ which was released in 2003. At the time, they weren’t officially an item yet, but their romance began shortly after filming the movie.

Jennifer Lopez & Ben Affleck were all set to tie the knot in Sept. 2003, but they called the wedding off one day before the nuptials were set to take place. "Due to the excessive media attention surrounding our wedding, we have decided to postpone the date," they explained at the time. "When we found ourselves seriously contemplating hiring separate ‘decoy brides’ at three different locations, we realized that something was awry."

However, the relationship lived on. Here, they’re pictured attending the Spirit of Liberty Awards Dinner in October 2003.

Related: Jennifer Lopez’s 50th Birthday Celebration

It’s no secret that Ben Affleck is a huge Red Sox fan, and even though Jen is from New York, she was the ultimate supportive fiancee while attending a Red Sox/Yankees game with him in Oct. 2003. At one point, Ben leaned in to whisper something into Jen’s ear as they watched the playoff game.

Ben Affleck and Jennifer Lopez were photographed spending time in Massachusetts in Dec. 2003. However, just weeks later, they would split. The breakup was confirmed in Jan. 2004, and both Ben and Jen wound up moving on. Of course, Jennifer married Marc Anthony and they had two kids together. They eventually split, and she got engaged to Alex Rodriguez in 2019. However, her relationship with Alex was also short-lived, as they broke up in 2021. Meanwhile, Ben was married to Jennifer Garner for 10 years before their June 2015 breakup, and they had three kids together. He was in a serious relationship with Ana de Armas for a year in 2020 and the beginning of 2021, as well.

Shortly after Jennifer’s split from A-Rod in 2021, she and Ben shocked fans by reuniting. At the end of April, reports surfaced that the two had been hanging out again, and there were photos of Ben exiting what appeared to be J.Lo’s car. 

Then, in May, they jetted off to Montana for a low-key trip to Big Sky Resort, and were photographed in the car together on the getaway. 

Two weeks after their romantic trip to Montana, Jen welcomed Ben to her Miami home just before Memorial Day 2021. The pair were both spotted on the balcony of her place, taking in the sunshine. 

This article originally appeared on Hollywood Life and is syndicated by Cheapism.

Ben Affleck steps out on the balcony of the waterfront property in a Green Monstah t-shirt, a nickname for the left field wall at Fenway Park. The couple have been enjoying time together in Miami as they continue to rekindle their romance.