Since making his debut in 1979, Ben Affleck has remained one of Hollywood's most successful and well-heeled stars. The actor, producer, and screenwriter is no stranger to the fans of the silver screen, boasting himself an enviable portfolio of high-profile films, including the Academy Award-winning Good Will Hunting, Argo, Batman v Superman: Dawn of Justice, Gone Baby Gone, and Shakespeare in Love. Aside from his triumphant career, the 50-year-old actor also makes headlines with his high-profile dating history, with both public and rumored romantic relationships. The handsome star seems to have the habit of dating A-list stars, from co-stars like Jennifer Garner to Playboy model Shauna Sexton. Read on to see Ben Affleck's past love and flings, and his current relationship.

According to US Magazine, Rothman was Affleck's high school sweetheart. The pair met as teens during a summer camp and dated on and off for 7 years. Their classic relationship ended in 1997, shortly after Affleck shot to fame with Good Will Hunting. Now, Rothman is a short-film director.

Ben Affleck's A-list dating habit began in 1997 after he parted with school sweetheart Rothman. At a party held by tycoon film producer Harvey Weinstein, Affleck met and fell for Gwyneth Paltrow. At the time, Paltrow was already a rising star, having dated celebrities such as Brad Pitt.

Paltrow was Affleck's first celebrity romance. The couple dated for 3 years before calling it quits in 2000. During their romance, Paltrow and Affleck co-starred in the comedy-drama film Shakespeare in Love.

In 2009, Paltrow received a Grammy Award nomination for the Best Spoken Word Album for Children for Brown Bear and Friends. She is still active in her motion picture career, with the most salient role as Pepper Potts, Iron Man's wife in Marvel Cinematic Universe.

Affleck met Lopez while filming for the film Gigli. After the Anaconda actress parted with Cris Judd in 2022, she and Affleck got engaged that November when the Gone Girl actor popped the question with a $2.5 million diamond ring.

They soon rose to be one of Hollywood's power couples and were given the name 'Bennifer' during their romance. Unfortunately, the media frenzy and excessive tabloids scrutiny led to the couple's postponement of their wedding. The two announced their breakup in January 2004.

The couple is reported to have rekindled their relationship in May 2021, when they were spotted spending time together in Montana. In April 2022, Lopez officially confirmed that they have been engaged for the second time.

Another Jennifer and possibly Affleck's longest relationship ever. Affleck met Garner when they co-starred in Pearl Harbor (2001) and Daredevil (2004). At the time, Affleck was in a relationship with the other Jennifer - which was Jennifer Lopez. The couple's romance came to light in October 2004, and they tied the knot in June 2005.

They shared three children together, Violet, Seraphina, and Samuel. Unfortunately, after their 10th wedding anniversary in 2015, the couple announced their separation, which Affleck later regarded as the most regretful decision in his life. The Live By Night actor put the blame on alcoholism.

While they're no longer partners, the two have been keeping in contact to raise their children, who are currently in Los Angeles.

It was rumored that Affleck used to have a fling with Enza Sambataro, spouse to Boston Red Sox player Kevin Youkilis in 2004. Their short-lived romance lasted only two months.

The main cause of their split is excessive tabloid interference. Sambataro explained: 'It's not fun to have people write bad things about you, about things you did when you were 16 years old.'

Despite expressing her indignation toward the press, Sambataro still looked up to Affleck and claimed the Justice League actor was the most down-to-earth man she'd ever met.

Although they tried to stay under the radar for 2 years, Affleck and Lindsay Shookus' romance finally came to light in July 2017. The Justice League actor was alleged to have an affair with the Saturday Night Live producer while still being married to Jennifer Garner in 2015.

They split in August 2018, before reconciling in February 2019, only to call it quits two months later. It's revealed that their split was because the couple were too packed in schedules to spend time together.

Sexton is a well-known adult model. In 2018, she was spotted with the Good Will Hunting actor at Nobu in Malibu. Their fling quickly ended within just two months, after the couple traveled to Montana.

Affleck's friend later revealed that the famous actor decided to part with Sexton on the grounds that he had other important things to focus on.

The youngest woman on this list, Ana de Armas is a rising star in the silver screen industry. The couple was reported to meet while filming for their film, Deep Water. The couple's romance began to draw media attention in early 2020 when they were spotted visiting Cuba, the Knives Out actress's native country.

They were together for nearly a year before officially splitting in January 2021. According to US Magazine, the separation was because Armas couldn't manage to move between places to meet Affleck. While the actor is Los Angeles-based with his kids, Armas didn't want to take up permanent residence in LA.

After separation, Armas and Affleck are still on amicable terms, with the actress looking up to Affleck as a respectable senior in her job.