Ben Affleck Dating History: Jennifer Lopez, Jennifer Garner, & More

When it comes to high-profile relationships, Ben Affleck has had his fair share. After a breakup, the Justice League star has shown that he can maintain a friendship with an ex. Following her 2020 Academy Awards snub for her role in Hustlers, he showed his support for ex-fiancée Jennifer Lopez in a New York Times profile published in February of that year.

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There was no excuse for not including her.” Her authenticity is undeniably undeniable. He told the outlet at the time, “I keep in touch with her and have a lot of respect for her.” “Isn’t it incredible that she had her most successful film at the age of 50?” “Wow, that’s f–king amazing.” Fortunately, the kind words of the Argo director helped him out. Us Weekly announced the couple’s reconciliation in May 2021, after than a decade after they’d divorced.

“The old flame has been reignited to its full extent.” At the time, a source said, “They picked up where they left off in terms of affection for each other.” Lopez made the announcement in April 2022 that the couple was engaged for the second time. However, let’s go back in time! He began dating Jennifer Garner in 2004 after breaking off his engagement to Gwyneth Paltrow and having an on-and-off relationship with the “I’m Real” singer. After six years of marriage, Violet and Seraphina, as well as Samuel, the couple’s three children, announced their divorce in June 2015.

The 13 Going on 30 actresses has become a trusted confidant for Affleck, even in the midst of the actor’s recuperation. As one insider told Us back in 2017, “Jen has always been the person who can get through to him. The best she can do, she says, “is keep Ben in line.” According to an insider who spoke to Us exclusively in August 2019, Affleck and Garner were doing “amazingly well” at parenting their children.

There have been rumors that he has had relationships with a number of his co-stars, including Garner, Lopez, and Paltrow. To name a few, in 1999, Affleck fueled relationship rumors with Salma Hayek and in 2001 with Jaime King. In the wake of his divorce from Garner, he insists he’s still looking for the real deal. In February 2020, Affleck told Diane Sawyer on Good Morning America, “I would want to have a relationship that was profoundly meaningful.” “As well as one to which I could devote myself fully.”

In March 2020, Us Weekly revealed that Affleck was seeing Deep Water co-star Ana De Armas, who played his love interest. “Ana’s friends are constantly telling her how lucky she is to have Ben and think he is so charming, cool, and fun,” an insider told Us at the time. “Ben is very supportive of Ana and tells her how amazing she is.” Their joy is contagious.” It was months before he found his way back to Lopez that the two of them called it quits.

According to a source in June 2021, “Friends believe they can see them staying together forever this time around.” “They’ve always been inseparable,” says the narrator. The following is a list of Affleck’s most memorable relationships and flings.

1. Cheyenne Rothman

Affleck dated Rothman in high school and the two were inseparable. Summer camp brought the two together, and they went on several dates over the next seven years before calling it quits in 1997.

2. Gwyneth Paltrow

At Harvey Weinstein’s invitation, Affleck and Paltrow first met in 1997 and began dating the following year. After that, the A-listers teamed up for the 1998 film Shakespeare In Love before calling it quits in the following year. Filming Bounce renewed their romance, but they broke up for the second time in the fall of 2000.

3. Jennifer Lopez

On the set of Gigli, Affleck met Lopez. In June 2002, Lopez and Affleck became engaged after their divorce from Cris Judd was finalized. During their romance, the Gone Girl actor and “On the Floor” singer, known as “Bennifer,” gained the power couple appellation. Almost twenty years after Lopez’s breakup with Alex Rodriguez, the two were reconciled once more. This couple has “always loved each other,” according to a person who met them in Montana in May of 2021.

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The couple was spotted kissing at a gym during a romantic vacation in Miami, and the Us confirmed that they were back together. According to the insider, “Ben and Jen feel so connected to each other very soon.” You can’t help but notice that the old flame has been reignited. When it came to their love for one another, they resumed where they left off. According to Lopez, the couple announced their second engagement in April 2022. The wedding date has been set for July 20, 2022.

4. Jennifer Garner

Although Affleck and Garner worked together on Pearl Harbor in 2001 and Daredevil in 2003, their relationship wasn’t officially announced until October of that year. In April 2005, the actor from The Way Back proposed, and they got married in Turks and Caicos in June of that year. When Violet and Seraphina were born in December 2005, Samuel was born in January 2009, and Seraphina was born in February of 2012.

A few months after their 10th wedding anniversary, the Live by Night actor and Alias star announced their divorce in June 2015. In October of last year, their divorce was finally formalized. In February 2020, the Oscar winner stated that his divorce from Garner was the “greatest regret” of his life. In the long run, shame is a health hazard. “Shame has no redeeming qualities,” he said in an interview with the New York Times. This is merely a nasty, terrible sensation of poor self-worth and self-loathing stewing away.

5. Lindsay Shookus

In July 2017, multiple sources told Us that Affleck and the Saturday Night Live producer had been dating since 2014 when Affleck was married to Jennifer Garner. According to a source close to Affleck and Garner, they were “having a full-blown affair.” When they could, they slept together, exchanged cute texts, and hung out together whenever they could. Affleck and Shookus appeared to be taking their relationship seriously when they moved in together to an NYC apartment in November of last year.

He briefly dated Shauna Sexton after they broke up in August 2018. In February 2019, Affleck and Shookus repaired their relationship, but they called it quits in April of the following year.

6. Shauna Sexton

At Nobu in Malibu, Affleck and Sexton dined together after their breakup at Shookus. According to a report from Us Weekly, the Argo actor and the Playboy model broke up in 2018 following a two-month relationship. After a trip to Big Sky, Montana, the couple decided to call it quits.

7. Ana de Armas

While filming Deep Water, Affleck and Armas became friends. When the two went on a Cuban vacation together in March 2020, they fueled romance speculations. After a few days of waiting in the security queue at a Cuban airport, a fan noticed the Town star and Knives Out actress “making out.”

Later on in the month, Us Weekly reported exclusively that the two were “happy together and officially dating. At the end of the month (May 2020), a source told Us that Affleck is “extremely serious” about her, and he wants his kids “to get a chance to meet [her].”

A source revealed to Us in January 2021 that they had amicably parted ways.