Jennifer Lopez is a self-proclaimed hopeless romantic, who got her happy ending when she reunited with ex Ben Affleck in 2021, almost 20 years after the two called off their first wedding in the early ’00s.

While Lopez references their long and winding love story on ninth studio album This Is Me ... Now (and the accompanying film), she also nods to the many high-profile relationships that preceded and followed her fairy-tale romance with Affleck. As she says narrating the trailer for This Is Me … Now: A Love Story: “Whenever someone asked me what I wanted to be when I grew up, my answer was always: ‘In love.’”

Bennifer may reign supreme today, but who came before and after Affleck? Ahead, we track all of Lopez’s marriages, engagements, and relationships—from her partnership with singer Marc Anthony to her rumored fling with Drake.

Ben Affleck (2021—present)

Bennifer surprised fans across the world when they rekindled their romance in April 2021, nearly two decades after calling off their initial engagement. Things quickly got serious, with Affleck and Lopez getting engaged for a second time the following year.

“Did you ever imagine your biggest dream could come true?” Lopez asked in a special edition of her fan newsletter, On the JLo. “Saturday night while at my favorite place on earth (in the bubble bath), my beautiful love got on one knee and proposed. 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, I was quite literally speechless and he said, ‘is that a yes?’ I said YES of course that’s a YES.”

The two officially tied the knot in a surprise Las Vegas ceremony in July 2022. They celebrated the nuptials with a second, more extravagant wedding in Georgia the following month.

At the tail end of that year, Lopez announced the forthcoming release of This Is Me ... Now, which was heavily inspired by her renewed romance with Affleck. “When he came back into my life, again the same thing happened, where I felt so inspired and so overtaken with emotion that it was just pouring out of me,” she told Zane Lowe in an interview for Apple Music. “When I feel good, I write music. And I wrote music, and I got in the studio in I think May, and by August when we got married, it was done.”

Affleck has similarly been open about his adoration for his wife since their unexpected reunion.

“She is incredibly knowledgeable about the way fashion evolves through the culture as a confluence of music, sports, entertainment and dance,” he told The Hollywood Reporter in March 2023.

And during a red carpet event, he told Entertainment Tonight, “She’s brilliant and [she] helps me in every conceivable way.”

Alex Rodriguez (2017—2021)

In a 2019 interview with Sports Illustrated, Lopez reflected on meeting MLB player Alex Rodriguez for the first time at a 2005 Yankees game in New York City: “We shook hands, and it was this weird electricity for, like, three seconds … Three to five seconds of looking at somebody right in their eyes, and getting stuck.”

But it would be over 10 years before the two eventually reconnected and started dating. “I was having lunch somewhere and I saw him as he passed by. Afterwards, I went outside, and for some reason I felt like tapping him on the shoulder,” Lopez recalled in 2017, during a guest appearance on The Ellen DeGeneres Show. “He texted me, said, ‘Let's go out to dinner,’ and I said, ‘Okay.’ We had a nice dinner.”

Throughout their yearslong romance, J.Lo and A-Rod made multiple high-profile appearances together at events like the Met Gala, the Golden Globes, the Oscars, and the Grammys. Rodriguez also accompanied Lopez to her performance at Joe Biden’s presidential inauguration in January 2021.

They announced their engagement in 2019, but plans for their wedding were postponed due to the outbreak of the COVID-19 pandemic in 2020. Then, in April 2021, the couple announced their split. “We have realized we are better as friends and look forward to remaining so,” they said in a joint statement at the time. “We will continue to work together and support each other on our shared businesses and projects. We wish the best for each other and one another’s children. Out of respect for them, the only other comment we have to say is thank you to everyone who has sent kind words and support.”

At the time, a source for E! News elaborated on Lopez’s reasoning for ending the engagement. “After months of questioning things and fighting, Jennifer felt like she could no longer trust Alex anymore,” the insider said.

Drake (2016)

Lopez was rumored to be dating Drake after the rapper was spotted cheering her on at her “All I Have” Las Vegas residency in December 2016. What followed was a streak of now-deleted cuddly Instagram posts, which included a photo of Lopez lying across Drake’s lap and another snap of the two embracing at a party. “She’s having fun,” a source told E! News at the time.

Lopez finally put the rumors to rest during a 2017 interview on The Daily Show. “Let me clear this up,” she said. “I am not with Drake.”

Drake seemed to reference the end of their fling in a 2018 track titled “Diplomatic Immunity,” on which he raps: “2010 was when I lost my halo / 2017 I lost a J.Lo.”

Casper Smart (2011—2016)

Lopez began dating Casper Smart, who worked for her as a backup dancer, shortly after her split from Anthony in 2011. A source told People that the romance with Smart, who is 18 years her junior, was “a fun fling” and “not meant to turn into anything more.” The two developed an on-again, off-again relationship before ultimately calling it quits in 2016.

Although initial reports claimed that the breakup was amicable, an insider later told People that Smart had cheated on Lopez. “She kicked him out because he cheated on her and he got caught,” the source said. “It happened two years ago, and he promised he would never do it again, and once he did, she was done.”

Marc Anthony (2004—2011)

When Lopez met musician Marc Anthony while he was performing in Paul Simon’s 1998 Broadway musical The Capeman, he allegedly first told her, “One day you’re going to be my wife,” according to Lopez’s memoir True Love. Over the years that followed, Lopez and Anthony maintained a close friendship, with the two collaborating on music together despite seeing other people.

Months after ending her first engagement to Affleck, Lopez married Anthony in a secret ceremony in June 2004. Years later, she reflected on receiving support from Anthony after that first breakup with Affleck. “To have one of my best friends, who I’d known for years, who I actually love and did have chemistry with, come into my life and say, ‘I’m here,’” she told Today in 2014. “What you need to know is, nobody can save you or heal you. Only you can do that for you.”

In 2008, the couple welcomed twins Max and Emme. “Jennifer and Marc are delighted, thrilled, and over the moon,” Lopez’s manager told People at the time.

The couple officially went their separate ways in 2011, but they continued to be close friends and collaborators. Just a few months after they separated, they worked together as judges on dance competition series Q’Viva! The Chosen. In 2016, they released a cover of “Olvídame y Pega la Vuelta,” which they performed together at the Latin Grammys later that year.

“Honestly, we’re always gonna be great friends. I’m always gonna be there for him; he’s always gonna be there for me,” Lopez said of her ex-husband in a 2017 interview on Live With Kelly.

In 2018, Lopez credited Anthony with boosting her self-esteem as a singer. “While I was married to Marc, he really helped me with my confidence, and he saw where I suffered,” she said on Sunday Today. “[He would say,] ‘You’re a great singer. Don’t ever let anybody tell you you’re not a great singer.’ And I respected him so much because I consider him one of the best singers of all time.”

Anthony similarly praised Lopez after their split. During a 2017 red carpet interview with Extra, he said, “We’ve always been [in a good place] from day one, you know. We met working—20-something years ago we met, working. She’s my goombah—that’s my girl—for life.” He added, “If you want to get along with a woman, just get divorced.”

Ben Affleck (2002—2004)

Lopez met Affleck in 2001 on the set of rom-com Gigli, in which they costarred. Shortly after going public with her split from husband Cris Judd, Lopez and Affleck debuted their relationship—and Bennifer was born.

Bennifer reigned the early 2000s as the It couple. Lopez later reflected on the media frenzy over their romance in a 2016 interview with People: “We didn’t try to have a public relationship. 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.”

They quickly got engaged in 2002, with Affleck famously proposing to Lopez with a 6.1-carat pink diamond from Harry Winston that reportedly cost him $2.5 million. But in 2003, they postponed their wedding. “Due to the excessive media attention surrounding our wedding, we have decided to postpone the date,” the pair explained in a joint statement at the time. “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.”

The wedding never happened, with the couple officially calling it quits by January 2004. Lopez called the end of their relationship her “first big heartbreak” in a 2014 interview with Today.

Despite that, the two periodically kept in touch over the years (and through their different marriages). “We don’t have the kind of relationship where she relies on me for advice,” Affleck told The Hollywood Reporter in 2012, when he was married to actor Jennifer Garner. “But we do have the kind of relationship where there’ll be an email saying, ‘Oh, your movie looks great.’ I remember when she got American Idol. I said: ‘This was really smart. Good luck.’”

And, as fate would have it, their story didn’t end there.

Cris Judd (2001—2002)

Lopez met her second husband, choreographer and dancer Cris Judd, on the set of her “Love Don’t Cost a Thing” music video, which he directed. The two got married in September 2001 and filed for divorce just nine months later, in July 2002.

"Coming out of a torrid relationship, I meet this sweet person who’s so refreshing,” Lopez explained in a 2003 interview with Vibe. “But marriage is not just about love. I thought I had learned that in my first marriage … I loved Cris, still love him, he’s one of the best people. This wasn’t an easy thing to walk away from, but we didn’t have what it takes to make a marriage work.”

As for Judd, he reflected on their brief relationship in a 2014 interview with Us Weekly, citing the difficulties of being connected to a high-profile celebrity. “You know, it’s very tough,” he said. “Your privacy is breached. You’re no longer a normal person. [Our wedding] was a circus. I think several people got arrested trying to climb up a mountain … trying to sneak in. We actually rented the airspace.”

Ultimately, the privacy issues didn’t contribute to the breakdown of their marriage. “It had no bearing on the outcome of a relationship,” he said. “Unfortunately, it just didn’t work out.”

Sean “Diddy” Combs (1999—2001)

Lopez famously began dating Sean Combs—a.k.a. Puff Daddy, a.k.a. P. Diddy, a.k.a. just plain Diddy—in 1999, around the time she released her debut album, On the 6. Together, the two were one of Hollywood’s biggest power couples, with Diddy by Lopez’s side for some of her most career-defining fashion moments. (Who can forget that plunging green Versace dress at the 2000 Grammys?)

Two years after they broke up, Lopez reflected on the relationship in an interview with Vibe, hinting that infidelity had led to the split.

“It was the first time I was with someone who wasn’t faithful,” she said. “I was in this relationship with Puff where I was totally crying, crazy, and going nuts, it really took my whole life in a tailspin … I never caught him, but I just knew. He’d say he was going to a club for a couple of hours and then never come back that night.”

Ojani Noa (1997—1998)

Lopez met her first husband, Ojani Noa, while he was a waiter at a Cuban restaurant in Miami. They wed in 1997 before divorcing in January 1998, after 11 months of marriage.

The two seemed to remain on good terms for some time, with Lopez even hiring Noa to manage a Cuban restaurant she opened in Los Angeles in 2002 for a $1,000 a week. When she fired him six months later, Noa reportedly sued her for breach of contract. The lawsuit ended in a settlement that prohibited Noa from publicly disparaging or revealing intimate details about Lopez for monetary gain. Despite that, Noa began to shop around for a book that covered his brief marriage to Lopez, for which she sued him in 2006.

Things got even more hostile in 2009, when Lopez sent cease-and-desist letters to Noa for beginning production on a mockumentary titled How I Married Jennifer Lopez: The J.Lo and and Ojani Noa Story. The movie's producer, Claudia Vazquez, attempted to sue Lopez for $10 million for interfering with the production. A judge ultimately dismissed the lawsuit.

Throughout the years of legal conflict, Noa and his business associates threatened to release home-video tapes of Lopez from their honeymoon—though a judge banned the tapes from being released in 2009.

As an associate editor at HarpersBAZAAR.com, Chelsey keeps a finger on the pulse on all things celeb news. She also writes on social movements, connecting with activists leading the fight on workers' rights, climate justice, and more. Offline, she’s probably spending too much time on TikTok, rewatching Emma (the 2020 version, of course), or buying yet another corset.