It is no secret how daunting it can be for celebrities to have their private lives constantly publicised, judged, speculated and criticized. Almost every relationship, decision and life event is impossible to keep secret, so not only are their lives constantly in the media, so are all their choices, good or bad. Stars Jennifer Lopez and Ben Affleck have had one rollercoaster of a relationship ride, and we have been there for it all. From the moment they met on the set of their film Gigli in 2003, there was electricity between the two they couldn’t deny. Now over a decade later they have found their way back to each other. After many failed relationships, ex husbands and wives, five children, a trip to rehab, and many accolades later, Lopez and Affleck believe in giving their connection another chance. Sometimes time is all we need to put things into perspective, and sometimes the person that is right for us is right under our nose, for these two lovebirds, things seem to have taken a turn for the better this time around. Here is a timeline of the history of Jennifer Lopez and Ben Affleck’s relationship from start to now.
Singer, actress, and dancer Jennifer Lopez, began appearing as a Fly Girl dancer on In Living Color, where she remained a regular until she decided to pursue an acting career in 1993. Lopez ventured into the music industry with her debut studio album On the 6 in 1999, and later starred in the psychological horror The Cell 2000.
After starring in Gigli in 2003, despite it being a critical and commercial failure, Lopez went on to star in the successful romantic comedies Shall We Dance? 2004 and Monster-in-Law (2005). Lopez is considered a pop culture icon, with a cumulative film gross of US$3.1 billion and estimated global sales of 70 million records, Lopez is regarded as the most influential Latin entertainer in North America. Forbes ranked her as the most powerful celebrity in the world in 2012.
Actor, film director, producer, and screenwriter Ben Affleck began his career as a child when he starred in the PBS educational series The Voyage of the Mimi between 1984 and 1988. His accolades include two Academy Awards and three Golden Globe Awards.
After a career downturn, he starred in Daredevil and Gigli where he co-starred with Lopez in 2003, Affleck received a Golden Globe nomination for portraying George Reeves in the noir biopic Hollywoodland in 2006.He then directed, co-wrote and starred in the crime drama The Town 2010 and directed and starred in the political thriller Argo (2012); both were critical and commercial successes. Affleck has made quite a successful career for himself. He has won a Golden Globe and BAFTA Award for Best Director, and the Golden Globe, BAFTA, and Academy Award for Best Picture.
2001: They Meet
The pair first met on the set of their movie, Gigli. While the movie didn’t do too well at the box office, their relationship took off quickly. J.Lo was still married at the time, to her second husband, Cris Judd. But she filed for divorce shortly after meeting Affleck.
She and Affleck went public with their relationship soon after her divorce from Judd, which was finalized in 2003.
2002: Affleck Makes An Appearance in “Jenny From The Block”
It was released by Epic Records on September 26, 2002, as the lead single from her third studio album This Is Me... Then 2002. The song, first leaked online, was written by Lopez, Troy Oliver, Mr. Deyo, Samuel Barnes, Jean-Claude Olivier, and Cory Rooney.
The now iconic music video featured a very steamy moment between the two, which put their relationship in the spotlight. In 2010, J.Lo spoke of the pressures that the media put on their relationship. During a guest appearance on The Graham Norton Show, J.Lo expressed, "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."
November 2002: They Get Engaged
Lopez and Affleck were engaged. Affleck proposed using a 6-carat pink diamond ring reportedly costing $2.5 million. J.Lo confirmed the happy news in an interview with Diane Sawyer, "It's the most magnificent thing I've ever seen," she expressed.
Affleck proposed to Lopez at his mother’s house in Boston, complete with rose petals, candles, bouquets, and her song “Glad” playing in the background.
2003: They Star In Another Movie Together
J.Lo played the dead wife of Affleck’s character in Jersey Girl, an American comedy-drama film that was slated for a release in 2003 but was pushed forward and released in 2004.
It was the first film written and directed by Smith not to be set in the View Askewniverse. At $35 million, not including marketing costs, it was then Smith's biggest-budgeted film, and was a box office bomb, grossing just $36 million.
September 2003: Wedding Postponed
Days before the two were supposed to tie the knot, they released a joint statement announcing the ceremony was to be postponed. They cited "excessive media attention" but remained together.
In an interview covered by The Age, the pair had spoken out about their decision to postpone. "Due to the excessive media attention surrounding our wedding, we have decided to postpone the date." 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."
January 2004: Bennifer Is Over
On January 22, 2004, the pair officially ended their engagement. J.Lo confirmed the sad news through her spokesperson. "I am confirming the report that Jennifer Lopez has ended her engagement to Ben Affleck," the singer/actress' spokesperson said in a statement issued Thursday, January 22.
The break of the engagement wasn’t necessarily a breakup at the time. Affleck had been simply telling reporters that there are no immediate plans to reschedule their wedding, which had been postponed indefinitely back in September.
June 2004: J.Lo Moves On With Former Boyfriend
J.Lo officially ended her relationship with Affleck through a statement to the Associated Press, without giving much reasoning at the time. Lopez quickly moved on and married former boyfriend Marc Anthony just a few months later. The couple first dated back in 1999 after working on “No Me Ames” together.
In her 2014 book, True Love, J.Lo reflected on the difficult time between announcing her split from Affleck and marrying Anthony. "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."
2005: Ben Affleck Moves On With Jennifer Garner
Affleck also moved on soon after his break up with J.Lo. Affleck made his first public appearance at the World Series with Jennifer Garner, who he had originally met on set of Pearl Harbor in 2000.
He married Garner in 2005, and the couple welcomed three children together over the years, daughters Violet and Seraphina, and son Samuel. The couple later divorced in 2018.
2005-2018: 13 Years Later
Thirteen years passed in what felt like a blink of an eye. Affleck married Garner in 2005, and they had three children in the coming years, and Lopez and Anthony had twins, Emme and Maximilian, in 2008. But in 2011, their romance burned out, as they endured a bumpy divorce just three years later.
After the two had ended their marriages, both were dating other people before they were to reunite again in 2021.
2011: J.Lo’s Alleged Relationship With Rodrigo Santoro
In 2012 soon after her split from Marc Anthony, Jennifer Lopez starred in the rom-com What To Expect When You're Expecting alongside actor Rodrigo Santoro.
Neither Jennifer nor Rodrigo ever confirmed a relationship, it has definitely been rumored that the two were more than just friends.
2011: J.Lo’s Alleged Relationship With Bradley Cooper
Another Hollywood star that was rumored to have dated Jennifer Lopez is actor Bradley Cooper. Once again neither of the stars ever confirmed anything, but in 2011 the two did seem a bit closer than usual.
The artists, who were seated close to each other at the Oscars on Sunday, may have been together following her divorce from Marc Anthony, but that’s something we will never know.
2011-2016: J.Lo And Casper Smart
Next on the list is former backup dancer Casper Smart with whom Jennifer Lopez was in an on-and-off-again relationship from October 2011 until August 2016. Lopez and Smart's relationship began as a professional one, when he was her backup dancer.
By Nov. 2011, rumors of a "fling" began to swirl. A couple weeks later the couple was photographed on vacation in Hawaii with Lopez and ex-husband Marc Anthony's twins. After about two-and-a-half years together, they ended their relationship in mid-2014, and remained "great friends" post-split.
2014-2018: Affleck And Lindsay Shookus
Though Affleck kept his romance with the Saturday Night Live producer under wraps until July 2017, multiple sources confirmed to Us Weekly that they had started hooking up in 2014 while he was still married to Garner.
Things appeared to be getting serious between the two, as they ended up moving into an NYC apartment together in November 2017. Affleck and Shookus called it quits in August 2018.
2016-2017: J.Lo’s Relationship With Drake
Drake and Lopez sparked dating rumors in December 2016 after the artist was seen at two of Lopez’s shows. While the two did not directly address any reports of their relationship, they did confirm their relationship the same month by posting matching photos on Instagram looking loved up.
But the flame died quickly. In February, news broke that Lopez and Drake had split up after less than two months of dating. Some people chalked up the fling to one big publicity stunt. But Drake insists that it was real. In an interview with Rap Radar, which came out later in 2019, Drake expressed “I have plenty of love for her,” he said. “We had great times together.”
2018: Affleck And Shauna Sexton
During this time and shortly after his break up from Shookus, Affleck was spotted dining with Sexton at Nobu in Malibu in August 2018. Ben Affleck's romantic fling with 22-year-old Playboy model Shauna Sexton, lasted throughout his time in an in-patient rehab treatment for alcohol addiction, and ended not long after it began.
Us Weekly had confirmed that Affleck ended his fling with the Playboy model in 2018 after two months. They called it quits after they traveled to Big Sky, Montana, together.
2017-2021: J.Lo And Alex Rodriguez
Jennifer Lopez and then-husband Marc Anthony attend a baseball game at Shea Stadium in Queens, New York, in May 2005 where they meet New York Yankee, Alex Rodriguez. In February 2017 Lopez and Rodriguez reconnected when they bumped into each other at a restaurant.
Rodriguez and Lopez got engaged while on vacation in the Bahamas, in March 2019. In April 2021 J.Lo and A-Rod broke up and called off their two-year engagement.
2020-2021: Affleck And Ana de Armas
Ben Affleck and Ana de Armas met while filming the psychological thriller "Deep Water" in New Orleans, Louisiana, in 2019. They began dating shortly thereafter and were frequently spotted together in Los Angeles, California, during the pandemic.
In January 2021, the actors ended their relationship after nearly one year of dating, multiple outlets had confirmed at the time.
April 2021: Bennifer Reunites
After J.Lo ended her engagement to Alex Rodrigues and Affleck split from Ana de Armas, the two had been spotted hanging out again. Page Six had reportedly spotted Affleck visiting J.Lo’s Los Angeles home multiple times.
While the two have not been spotted together, a source told Page Six, “Security picks him up at a nearby location and drops him off after spending a few hours at her house.”
May 2021: J.Lo and Ben jet off to Montana Together
Nearly two decades later, the actors departed for a weeklong vacation to Montana. Which follows their appearances together at Lopez’s L.A. mansion on the day they were set to depart.
A source exclusively tells E! News, "Ben has been making the effort to make it work with their schedules. He's really making a huge effort," the insider shares. "J.Lo thinks Ben has really stepped up and loves this version of him."
May 2021: Vacation For Two
By May 23, Affleck was spotted in Miami at the same waterfront mansion as J.Lo. There was speculation that he may have been wearing his watch from the “Jenny From the Block” music video in the paparazzi photos. The couple was seen working out and spending time together while in Miami.
On May 31, they were photographed cuddling at the Pendry Hotel in West Hollywood, where they went to dinner.
May 2021: Distance Won’t Keep Them Apart
People reported that while in L.A., the singer "spent time with Ben," adding, "They have kept in touch every day since their Montana trip." Determined not to let distance affect their reunion.
"It's a tricky situation since they live so far from each other, but they both seem committed to making things work,” tells a source.
May 2021: Showing Commitment
According to People the singer flew out to L.A to spend more time with Affleck, she was in L.A for a couple of days following.
“She spent time with Ben. They have kept in touch every day since their Montana trip... It's a tricky situation since they live so far from each other, but they both seem committed to making things work."
June 2021: Thinking About The Future
It appears these lovebirds are in it for the long haul this time around. They are working towards taking their recently rekindled relationship to the next level.
As reported by People, "They will continue to travel back and forth between Los Angeles and Miami," says the insider. "They are very happy together." The two are reportedly "slowly starting to talk about the future."
June 2021: The Couple are “Hopeful” This Time
The two are "hopeful about their relationship" this time around, a source tells ET. Although there have been many ups and downs in the past, together and apart, these two are really turning things around this time.
"J.Lo and Ben are very much a couple and have been telling friends that they're together," the source says. "When they first reconnected, they had to see if the spark was still there because it had been a while. It was, so now they are both fully in it."
June 2021: Closure For Their Past
According to ET's source, the pair has "talked about the past and why things didn't work out." They talk of their hope, and the effort they are both putting it to make their relationship work.
"This is not a casual relationship," the source adds. "They are taking it seriously and want it to be long-lasting."
June 2021: They Are Different People Now
Jen is thrilled and really trusts Affleck. Despite his troubled past, Affleck is more traditional and low-key in his values than he used to be, and this seems to be working really well for them. Lopez likes that they can go on dates and have fun, without pressure.
And while Lopez may appreciate Affleck's input, it seems the two are keeping their business and personal lives separate for now. "J.Lo and A-Rod were always investing together and mixing business with their relationship and Ben is less into that," ET's source says.
July 2021: Families Are Getting Along Well
Lopez’s twins from former husband Marc Anthony, and Affleck’s three children from former wife Jessica Garner, have come together. The families are beginning to bond more, according to E! News.
Following weeks of back and forth vacations and time spent together, Affleck finally joined Lopes and her children at a family birthday party and the two brought their kids together for a family trip to Universal Studios.
July 2021: How The Kids Feel
Sometimes it may be difficult for children to understand their parents choices, but for these celebrity kids, things seem to be going just fine for everyone.
E! News’ source notes that Lopez and Affleck's relationship "is not a big deal to either sets of kids," adding that the little ones "aren't super sensitive to the situation." Lopez and Affleck took their kids, Emme and Samuel, to their Brentwood Country Mart in Los Angeles. An eyewitness tells ET, "They were all enjoying their time there.”
July 2021: A Different Dynamic
After having introduced the families and spent some quality time together, the two seem to really be making a difference this time around. “She looked very happy to see him and they walked around the property together so she could show him around," A source at E! News tells.
The third source added, "She had a big smile on her face and was twirling in a loose summer dress. They spent the day inside together but came out a few times for fresh air and to admire the water view."
July 2021: Ben And Jennifer Taking The Next Step
The two are moving full speed ahead in their romance. A source tells ET that amid their rekindled romance, their "friends wouldn't be surprised if they move in together and ultimately end up together."
"They're spending all of their free time together and making each other a priority. J.Lo falls hard and has certainly done the same with Ben again this time around," the source says.
Alex Rodriguez Reacts To The Couples Reunion
There is no denying that many people are freaking out over the latest news of the reunion between the two former couple. But Lopez’s ex-fiance Alex Rodriguez has had a very different reaction than we might have expected.
A source close to J.Lo tells E! News the retired MLB player is flabbergasted more than anything else, especially since they officially broke up and called off their engagement just a month ago. "A-Rod is shocked that J.Lo has moved on," the source reveals. "He truly thought they would be able to make it work and reconnect. He has been reaching out to J.Lo trying to meet with her and she has been very short with him."
Jennifer Garner Reacts To The Couples Reunion
Despite Rodriguez’s not so happy reaction to the couple reunion, Affleck’s ex-wife and mother to their three children, seems to be in support of her ex-husbands reconciliation with ex Jennifer Lopez.
A source told In Touch that she believes they are a “great match” and “is really happy for them.” “She’s moved on with John Miller and Ben has moved on too!” the insider added. “She’s glad that he met a woman who is successful in her own right and isn’t using Ben for fame.”
Matt Damon’s Reaction To The Couples Reunion
Actor, producer, and screenwriter Matthew Damon was ranked among Forbes' most bankable stars. His successful career in films has collectively earned him over $3.88 billion at the North American box office, making him one of the highest-grossing actors of all time.
According to Us Weekly, “There’s not enough liquor in the world for you to get me to say something about that,” he joked, adding that he does hope the reunion was more than platonic. "I love them both. … That would be awesome,” Damon reacts.
Jennifer Lawrence’s Reaction To The Couples Reunion
Actress Jennifer Lawrence was the world's highest-paid actress in 2015 and 2016, with her films grossing over $6 billion worldwide to date. Appearing in Time's 100 most influential people in the world list in 2013, Lawrence has built an impeccable career for herself.
The Hunger Games actress teased during the May 13 episode of the "Bitch Bible" podcast after learning of Lopez and Affleck's Montana getaway. "I'm so excited. I'm so happy for them."
Bette Midler’s Reaction To The Couples Reunion
Singer, songwriter, actress, author, and comedian Midler began her professional career in several Off-Off-Broadway plays, prior to her engagements in Fiddler on the Roof and Salvation on Broadway in the late 1960s. She came to prominence in 1970 when she began singing in the Continental Baths. Midler’s career spans over seven decades, she has received numerous accolades, including four Golden Globe Awards and three Grammy Awards, and two Tony Awards.
“#BenAffleck & #JenniferLopez might be back together?" tweeted the Tony winner. "Aww. That's nice, but I was hoping that if we could bring anything back from the early 2000's it would be my pelvic floor muscles."
Spencer Pratt’s Reaction To The Couples Reunion
American reality television personality Spencer Pratt came to prominence after being cast in the series “The Hills,” after he began dating Heidi Montag, a primary cast member of the reality television series.
The Hills star retweeted a photo of the duo in the car captioned, "I had zero interest in any celebrity couples in 2002, other than Britney Spears and Justin Timberlake, so I missed the Bennifer train. I’m happy to announce, however, that I’m fully on board in 2021."
Chris Rock’s Reaction To The Couples Reunion
Stand-up comedian, actor, writer, producer and director Christopher Rock came to wider prominence as a cast member of Saturday Night Live in the early 1990s. He went on to more prominent film appearances, with starring roles in Down to Earth 2001, The Longest Yard (2005), the Madagascar film series (2005–2012), Grown Ups and Grown Ups 2 (2010-2013), Rock has won four Emmy Awards and three Grammy Awards. He was voted the fifth-greatest stand-up comedian in a poll conducted by Comedy Central.
"I'm so happy," the star said in an off-the-rails Good Morning America interview on May 11. "I gotta get on that Raya app! ... J. Lo's on Raya? Wow. ... Gigli 2, come on! Are you guys excited? That's all I care about right now."
Kevin Smith’s Reaction To The Couples Reunion
Filmmaker, actor, comedian, comic book writer, author, and podcaster Kevin Smith came to prominence with the low-budget comedy film Clerks (1994), which he wrote, directed, co-produced, and acted in as the character Silent Bob of stoner duo Jay and Silent Bob.
Smith, who directed the pair in the 2004 movie Jersey Girl, took credit for their "Bennifer" nickname after it started trending on social media. "It’s a name I first gave the kids during 'Jersey Girl' pre-production, before the world found out they were dating," he claimed via Twitter. "I’d later drop the name in an interview with the @nytimes. Shortly thereafter, it appeared in the article and then entered the vernacular."