Look Back at Ben Affleck's Dating History as His Relationship with Ana de Armas Grows Stronger

Ben Affleck is not just a movie superstar; he is also a real Hollywood lady-killer. If you have ever wondered about his relationships, then here is the actor's romantic history. 

Ben Affleck is currently in a relationship with Cuban actress Ana de Armas. After they were seen vacationing together in Havana, Cuba, the couple sparked dating rumors back in March.

Affleck and de Armas' relationship hit new heights in Costa Rica. The pair was even pictured having a romantic stroll down the beach. They also decided to quarantine together amid the pandemic.

Ben Affleck and Ana de Armas are seen on July 24, 2020 in Los Angeles, California. | Photo: Getty Images

Ben Affleck and Ana de Armas are seen on July 24, 2020 in Los Angeles, California. | Photo: Getty Images

In June, de Armas met Affleck's mother, Christine Boldt. She was spotted stepping off a private plane with Boldt and Affleck. According to a report, they went on a family vacation to Georgia.

To celebrate Affleck's 48th birthday in August, de Armas gifted him a custom-made BMW motorcycle, built from scratch by WYLD Garage Co. The couple was photographed taking the chic new ride.

In November, Affleck and de Armas spent their first Thanksgiving together. This month, the actress reportedly listed her home for sale and has moved into Affleck's home in Los Angeles.

The "Pearl Harbor" actor, who previously checked into rehab in 2001, 2017, and 2018, has demonstrated that he can still be on good terms with an ex regardless of separating.

CHEYENNE ROTHMAN

Affleck's high school sweetheart was Cheyenne Rothman. The two first met as teens at summer camp. For more than seven years, Affleck and Rothman dated until they called it quits in 1997.

Cheyenne Rothman at Brenden Theatres in Las Vegas, Nevada, United States in 2004. | Photo: Getty Images

Cheyenne Rothman at Brenden Theatres in Las Vegas, Nevada, United States in 2004. | Photo: Getty Images

GWYNETH PALTROW

Affleck first met Paltrow back in 1997, at a party hosted by the now-disgraced Harvey Weinstein. Later that year, the pair started a relationship. They co-starred in 1998’s "Shakespeare In Love."

They split in 1999, shocking fans. However, they rekindled their relationship while filming another movie. In late 2000, they called it quits a second time around.

Gwyneth Paltrow and Ben Affleck on March 7, 1999 at the Shrine Auditorium in Los Angeles, California. | Photo: Getty Images

Gwyneth Paltrow and Ben Affleck on March 7, 1999 at the Shrine Auditorium in Los Angeles, California. | Photo: Getty Images

JENNIFER LOPEZ

Affleck met Lopez on the set of their movie called "Gigli." They started a relationship and became engaged in November 2002, just months after Lopez's divorce from Cris Judd was finalized.

However, in January 2004, Lopez and Affleck announced the end of their engagement. During their relationship, the former power couple was popularly referred to as "Bennifer." 

Ben Affleck and Jennifer Lopez December 12, 2003 in New York City. | Photo: Getty Images

Ben Affleck and Jennifer Lopez December 12, 2003 in New York City. | Photo: Getty Images

JENNIFER GARNER

Affleck and Garner began dating in 2004. They tied the knot in June 2005 and divorced in October 2018. They have three children together, daughters Violet and Seraphina and a son, Samuel.

After their split, the acclaimed actress continues to support Affleck, including in his struggles with alcoholism. They have also been doing well co-parenting their children.

Ben Affleck and Jennifer Garner are seen on April 09, 2019 in Los Angeles, California. | Photo: Getty Images

Ben Affleck and Jennifer Garner are seen on April 09, 2019 in Los Angeles, California. | Photo: Getty Images

LINDSAY SHOOKUS

Affleck and Shookus had started hooking up in 2014 during his marriage to Garner. The two split in August 2018, and the actor briefly dated Shauna Sexton.

In February 2019, Affleck, whose accolades include two Academy Awards and three Golden Globe Awards, and Shookus reconciled their relationship. However, the two ended things for good that April.

Ben Affleck and Lindsay Shookus are seen on January 05, 2018 in Los Angeles, California. | Photo: Getty Images

Ben Affleck and Lindsay Shookus are seen on January 05, 2018 in Los Angeles, California. | Photo: Getty Images

SHAUNA SEXTON

Affleck was spotted with Sexton at Nobu in Malibu in August 2018 after calling it quits with Shookus. The actor only dated the Playboy model for two months, according to US Weekly.

Prior to their split, the Oscar winner and the model reportedly traveled to Big Sky, Montana together.  Their split reportedly happened just days after he completed a rehab stint for alcoholism.

Shauna Sexton at The Cosmopolitan of Las Vegas on July 29, 2018 in Las Vegas, Nevada. | Photo: Getty Images

Shauna Sexton at The Cosmopolitan of Las Vegas on July 29, 2018 in Las Vegas, Nevada. | Photo: Getty Images

Affleck and his new girlfriend, de Armas, are taking the next step in their relationship, as reported by PEOPLE. According to a friend of the actor, the couple's relationship continues to be strong.

Affleck and de Armas "seem great," an insider previously told the publication. The insider added, "Everyone seemed very happy. Ana has been traveling so she had not seen the kids for a while."

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