J.Lo & Ben Affleck’s Relationship Timeline Includes His Dunkin’ Dream Job

The early 2000s are having a major resurgence with the returns of Gossip Girl, emo culture, and Bennifer. Jennifer Lopez and Ben Affleck practically created celebrity couple culture when they dated for two years and then got engaged in 2003, earning them the Bennifer nickname from the press. The moniker marked the first viral celebrity portmanteau, and it was the same tabloid attention that made them quickly call off the wedding and go their separate ways in 2004. Now, more than 18 years, two marriages, and several children later with other people, Bennifer has somehow found their way back to each other.

And on April 8, 2022, J.Lo announced that she and Affleck were engaged. Four days after announcing their proposal, she revealed on April 12 that Affleck proposed at her “favorite place on Earth”: the bubble bath. J.Lo was apparently too stunned that he had to ask her, “Is that a yes?” She told fans, “I said YES of course that’s a YES.”

The duo has always had nothing but nice things to say about each other while apart, with Affleck even agreeing with the masses that Lopez should’ve been nominated for an Oscar in 2020, but a reunion always seemed far-fetched. However, their friendship started growing into a renewed romance sometime in the summer of 2021, after J.Lo broke up with ex-fiancé Alex Rodriguez and Affleck split from then-girlfriend Ana de Armas.

Nothing proved their rekindled love more than Affleck’s 2022 Valentine’s Day gift to her. In a letter sent to fans on Feb. 14, Lopez revealed that Affleck made a montage celebrating their love story. Soundtracked by J.Lo’s Marry Me tune “On My Way,” the video features clips and pics that will fuel your 2000s nostalgia, including photos from the Gigli premiere and “Jenny From the Block” video — as well as Good Will Hunting snippets with his BFF Matt Damon for no explicable reason.

After watching the video gift from Affleck, Lopez reacted in a letter to her fans: “Watching it made me think about the journey of true love, its unexpected twists and turns, and that when it’s real, it actually can last forever. This seriously melted my heart.” The actor kept melting her heart when he asked J.Lo to marry him. “I was smiling so big and tears were coming down my face, feeling so incredibly happy and whole,” she wrote in another email to fans. “It was nothing fancy at all, but it was the most romantic thing I could’ve ever imagined... just a quiet Saturday night at home, two people promising to always be there for each other.”

Bennifer’s revival has proven that the 2000s are back — and now, after two (!!) weddings in Las Vegas and Georgia, you may be wondering, how did this all begin? Here’s everything to know about their relationship from 2002 to 2023, including their highs, lows, and immeasurable growth.

April 2002: Ben Makes His First Move

Lopez and Affleck met on the set of their movie Gigli in late 2001. But Affleck made his first public move in April 2002, when he took out a full-page ad in The Hollywood Reporter to praise his co-star. “You have shown kindness, dedication, diligence, humility, graciousness of spirit, beauty in courage, great empathy, astonishing talent, real poise and true grace,” he wrote. “It has been nothing but an honor and a pleasure to work with you. I only wish I were lucky enough to be in all your movies.” He signed off his letter by writing, “With love, respect and gratitude, Ben Affleck.”

July 2002: Lopez Files For Divorce

Months after Affleck made his move, he was seen locking lips with J.Lo at a surprise party for the singer’s 32nd birthday. Just two days later, Lopez filed for divorce from her then-husband Cris Judd, revealing that they had been separated for more than a month.

November 2002: Bennifer Is Born

While the whole world knew they were already an item thanks to PDA-filled paparazzi shots, J.Lo made her relationship with Affleck official in a way only she could: through an iconic music video. Bennifer made their public debut in her “Jenny From the Block” video, where the couple relaxes on a luxurious yacht (and Affleck literally kisses J.Lo’s butt) as helicopters try to get photos of them, poking fun at tabloid culture. The song went No. 1 on the Billboard Hot 100.

They also announced their engagement, revealing that Affleck proposed with a pink diamond ring (it even inspired a Charli XCX song almost two decades later). In an interview with Diane Sawyer at the time, J.Lo said that he planned an intimate proposal at his mother’s Boston home, soundtracked by her music. “It’s just a blanket, a quilt of rose petals, all over the whole entire house,” she said. “So many candles, and vases, bouquets. And my song ‘I’m Glad’ was playing. I walk in and I was just, like, overwhelmed. I wasn’t expecting it, and I was just like, ‘Oh my God.’”

August 2003: Gigli

By the time Gigli was released in August 2003, Bennifer had become a bonafide pop culture phenomenon, but that wasn’t enough to save it. Gigli was panned from all angles, grossing $7 million against a $75 million budget to become one of the worst box office bombs in history. Critics have also called it one of the worst films of all time. The reception was so bad that filmmaker Martin Brest hasn’t directed a movie since. It didn’t detrimentally affect Bennifer’s individual careers, but it also didn’t help alleviate their intense media attention at the time.

September 2003: A Canceled Wedding

Just a day before their highly publicized wedding date of Sept. 14, 2003, Lopez and Affleck decided to call off their wedding due to the media attention. “When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realized that something was awry,” they said in a statement to ABC. “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.” At the time, Bennifer simply said they were postponing their ceremony, but that soon wouldn’t be the case.

January 2004: Bennifer Calls It Quits

Bennifer announced their split much more subtly than they revealed their partnership, with J.Lo’s rep simply confirming the end of their engagement to The Associated Press at the beginning of 2004. “At this difficult time, we ask that you respect her privacy,” the rep said.

February 2020: Affleck Says J.Lo Was Snubbed By The Oscars

In 2020, J.Lo earned nominations at many award shows, including the Golden Globes and SAG Awards, for her critically beloved performance in Hustlers, but the Academy Awards opted not to recognize her, leading to an outcry from fans. Even Affleck agreed that his ex was majorly snubbed in a New York Times profile. “She should have been nominated,” he said “How awesome is it that she had her biggest hit movie at 50? That’s f*cking baller.” During the interview, he also mentioned that he maintained a friendly relationship with Lopez. “She’s the real thing,” he said. “I keep in touch periodically with her and have a lot of respect for her.”

April 2021: Lopez & Affleck Agree They Both Aged Well

Affleck (along with many of her close friends and colleagues) said some kind words about Lopez for her InStyle cover story in April 2021, even questioning his former girlfriend about her secrets for flawless aging. “Where are you keeping the fountain of youth?” he asked. “Why do you look the same as you did in 2003 and it kind of looks like I’m in my 40s … at best.” J.Lo laughed at his praise and complimented him right back. “Ben is funny! He still looks pretty good too,” she said.

May 2021: Bennifer’s First Reunion

At the very end of April, fans had their first potential Bennifer sighting when Affleck was seen leaving Lopez’s house just weeks after their respective splits from de Armas and Rodriguez. At first, the spotting was just dismissed as a friendly catchup, with Page Six reminding readers that “they’ve never not been” friends. However, on May 11, E! reported that the twosome had spent the past week together on vacation in Montana, where Affleck has a home. “It’s natural between them and the chemistry is unreal,” a source told the outlet. “They picked up where they last left off and are enjoying each other’s company right now.”

Later that month, People reported that the burgeoning couple was “in touch every day” and making plans to see each other while J.Lo was in Miami spending time with her kids. Cue Affleck showing up in the city just four days later on May 23 for Memorial Day weekend. Now, fans were ready to make it official: Bennifer was back.

June 2021: Bennifer 2.0’s First Kiss

On June 13, after weeks of speculating that Bennifer was really official once again, fans got all the confirmation they needed after Page Six posted photos of the couple locking lips at Nobu in Malibu. Their dinner was a family affair to celebrate Lopez’s sister’s birthday, which was also attended by her twins, Max and Emme, making it clear that Affleck was a part of the family once again. Neither of them had yet to confirm their romance or comment on the speculation, but their kiss spoke a thousand words.

September 2021: Bennifer’s Red Carpet Comeback

Lopez and Affleck made their reunion official in a way that only a couple as famous and glamorous as Bennifer can do. The duo made their red carpet comeback at the 2021 Venice Film Festival, where J.Lo supported Affleck at the premiere of his movie The Last Duel. They even locked lips on the red carpet, leaving no doubt in anyone’s mind that the romance was back for real.

February 2022: J.Lo Tells All

To promote her rom-com Marry Me, J.Lo dished about her new romance with Affleck for the first time to People, saying that she’s “so lucky and happy and proud to be with him,” especially after nearly two decades. “It’s beautiful the way it feels very different than it was years ago,” she said. “There’s more of an appreciation and a celebration for it, which is nice. When you find somebody and you really, really love them and you get a second chance at that? That is a really rare, precious, beautiful thing and we don’t take it for granted.”

The singer also noted how much Affleck has grown in the time that they spent apart. “I’m so proud of the man he’s become that I’ve watched from afar,” she said. “To see the person, the human being, the man that he is today, the father that he is today, the partner that he is — he is so everything I always knew he was and wanted to be.”

Lopez was more tight-lipped when she talked to Rolling Stone for her cover story, warning that she “won’t talk about it a lot,” but she did re-assure fans that she and Affleck wouldn’t have reunited if they were worried about it having the same fate as their first try. “I don’t think we would have got back together if we thought that was where it was headed,” she said. “We feel like what we found again is so much more important, and how we protect that and how we live our lives — what to share, what not to share — is the balance that we have now, the benefit of experience and the wisdom that we gained over the years.”

That month, Affleck returned the favor and accompanied Lopez to the Los Angeles premiere of Marry Me, barely paying attention to the cameras because he was too busy kissing her head on the red carpet. On Feb. 13, the couple was spotted adorably dancing together in a suite while attending the Super Bowl. Is there a better way to promote your rom-com than showing how in love you are?

March 2022: Ben Cheers On His “Icon”

On March 22, J.Lo gave a heartfelt speech to accept the Icon Award at the 2022 iHeartRadio Music Awards. While she didn’t mention her beau directly, she directed her speech at her fans in the adoring crowd, which included a smiling and supportive Affleck. “Because of you, I get to do what I love the most in life and that is the most wonderful blessing,” she said. “That’s a gift that you give me and I just want to say thank you for that. You guys are the ones who give me the opportunity every day to live a life I couldn’t even imagine would come true when I was a little girl growing up in the Bronx.” Her daughter, Emme, and Affleck’s son, Samuel, were also in the crowd, making it a true family affair.

April 2022: Bennifer Gets Engaged — Again

On April 8, J.Lo announced her engagement to Affleck in her “On the JLo” newsletter, sharing a video of her beautiful green engagement ring with her fans, which was soundtracked by “Dear Ben,” her 2004 love song to her then-and now-fiancé. “You’re perfect,” J.Lo is heard singing.

In a new newsletter on April 12, Lopez told her fans about the intimate proposal, revealing that Affleck popped the question while she was at her “favorite place on Earth”: the bubble bath. “I was taken totally off guard and just looked in his eyes smiling and crying at the same time trying hard to get my head around the fact that after 20 years this was happening all over again,” she wrote. In fact, she was so shocked that Affleck had to ask her, “Is that a yes?” She told fans, “I said YES of course that’s a YES,” she wrote.

In a video attached to the email, J.Lo shared more details, revealing that “Affleck said some words I’ll never forget.” She also explained the meaning of her bold engagement ring. “Green is my favorite color, it’s also my lucky color. Obviously, it’ll be my lucky color forever now,” she said. “It means so much when somebody really thinks about you and loves you and sees you, and it was just the most perfect moment. We’re so lucky. It’s not often we get a second chance at true love.” It turns out that Affleck was the one filming the whole time. “We feel so lucky, and I love you,” she concluded, to which he revealed himself and responded, “I love you too.”

May 2022: Mother’s Day Throwback

To commemorate Mother’s Day on May 8, J.Lo shared a very fitting throwback video of her and Affleck wishing their moms a happy Mother’s Day while sitting court-side at a basketball game in the early 2000s. “Happy Mother’s Day to all the mommy’s out there!!!” she captioned the Instagram post. The announcer called Bennifer “Hollywood’s hottest couple” after they spoke to the camera, which is a title that remains true again 20 years later.

June 2022: J.Lo Mentions Ben In Speech

On June 5, J.Lo won the Generation Award at the MTV Movie & TV Awards, which was presented by her Second Act co-star Vanessa Hudgens. While Affleck wasn’t present at the ceremony, she still gave him an adorable shoutout in her emotional acceptance speech and made it clear that he was waiting for her. “Ben and everybody at home, hi!” she exclaimed. “Wait for me to have dinner, I’ll be home by 7!”

July 2022: Bennifer Ties The Knot At Last

It seems the green engagement ring really was lucky. 20 years after they first started dating, Lopez and Affleck finally made it down the aisle, according to a TMZ report on July 17. The wedding happened the day prior at A Little White Wedding Chapel in Las Vegas, per E!, citing a representative for the venue.

Lopez later wrote about the wedding in her newsletter, On the JLO, explaining that she donned “a dress from an old movie” while Affleck wore a suit from his own closet. But they almost didn’t make it on time because of delays in getting their marriage license before the ceremony. “We barely made it to the little white wedding chapel by midnight,” she said. “They graciously stayed open late a few minutes, let us take pictures in a pink Cadillac convertible, evidently once used by the king himself (but if we wanted Elvis himself to show, that cost extra and he was in bed).”

August 2022: A Second Wedding

Though Bennifer’s Las Vegas wedding was a whirlwind affair, they had a more elaborate celebration the following month. On Aug. 20, People reports, Lopez and Affleck got married (again) on the Gone Girl star’s private island property near Savannah, Georgia. This time around, the couple invited their family and friends to celebrate their nuptials, including stars like Matt Damon, Kevin Smith, and Jason Mewes, throwing a multi-day celebration for guests.

A couple of weeks later, J.Lo shared photos from their Georgia ceremony and wrote about her special day for her On the JLO newsletter. “Years ago, we had no idea the road ahead would mean navigating so many labyrinths and hold so many surprises, blessings, and delights,” she wrote. “It all culminated at this moment, one of the most perfect of our lives. We couldn’t have been happier.”

February 2023: They Make Their Grammys & Super Bowl Debuts

On Feb. 5, the married couple had a date night at the 65th Grammy Awards, marking the first time they attended the event together. Though the Gone Girl star looked bored at certain times of the night, Affleck was there in full support of Lopez, who presented an award.

A week later, Bennifer made their Super Bowl commercial debut. As a very well-known Dunkin’ customer, the company tapped Affleck to direct and star in their first-ever Super Bowl commercial, a job that he was much more enthused by than attending the Grammys. For the ad, Affleck worked the drive-thru at a Dunkin’ location in Medford, Mass., near his adopted hometown of Boston, surprising unsuspecting customers and even taking selfies through the window.

Lopez makes a surprise appearance at the end, utterly confused by her husband’s new job. “Is this what you do when you say you’re going to work all day?” she asks, before quickly realizing the benefit of Affleck working at Dunkin’. “Grab me a glazed,” she concluded.