Affleck’s love story starts out with film director Cheyenne Rothman. The pair reportedly became high school sweethearts after they met at summer camp when they were teenagers, and they reportedly dated on and off for over seven years before calling it quits in 1997, following Affleck’s rise to fame with Good Will Hunting. Little else is known about their romance.

Following his split from Rothman, Affleck began dating Gwyneth Paltrow, who he first met at a dinner party. They went on to star in two films together, Shakespeare in Love and Bounce, but after three years of dating on-and-off-again, the pair went their separate ways in late 2000. “I just think we have a very different sort of value system,” Paltrow later told Diane Sawyer when asked about their split. ”Ben makes life tough for himself. He’s got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out.”

Affleck and Lopez first crossed paths in late 2001 on the set of Gigli, though at the time, Lopez was still married to her second husband, dancer Cris Judd. In July 2002, Lopez had filed for divorce from Judd, and not long after, Bennifer was born. By November, the couple was engaged, and fans were shocked when the two decided to call off their wedding just days before it was set to take place in September 2003.

“When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realized that something was awry,” they said at the time in a statement, per People. “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.” In January 2004, four months after postponing their wedding, they called off their engagement all together.

Lopez later blamed the excessive media attention for their relationship’s demise. "We didn't try to have a public relationship," she told People in 2016. "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... I think different time different thing, who knows what could've happened, but there was a genuine love there." And now it seems they’re going to get that chance.

Following his highly-publicized split from Lopez, Affleck fell for yet another co-star, Jennifer Garner, who he met on the set of Daredevil. The two confirmed they were dating in October 2004, and six months later, Affleck popped the question. By June 2005, they were married, and fans thought the couple would be together for life.

Things seemed to be going well for the actors as they welcomed their daughter Violet in December 2005, their second daughter Seraphina in January 2009, and their son Samuel in February 2012. But not long after celebrating their 10-year wedding anniversary in June 2015, Affleck and Garner decided it was time to go their separate ways. By October 2018, the pair was officially divorced, and Affleck later said the “biggest regret” of his life was not fighting for his marriage.

“The biggest regret of my life is this divorce,” he told the New York Times during a 2020 interview. “Shame is really toxic. There is no positive byproduct of shame. It’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing.” Luckily, it seems like the two have since established an amicable co-parenting relationship.

After his marriage with Garner ended, Affleck decided it was time for him to get back out there. The actor went public with Lindsay Shookus, a Saturday Night Live producer, in July 2017, and though Affleck and Shookus never confirmed how they met, a source for Page Six reportedly claimed the two met through SNL, as Affleck has served as SNL host five times over the years. The two dated off-and-on before they reportedly split for good in April 2019.

While Affleck was on a break from Shookus in August 2018, the actor was reportedly spotted on a dinner date with model Shauna Sexton. The two went on to date for two months, even taking a trip to Montana together, before they went their separate ways in October 2018. “He enjoyed being with her but is working on himself, and being together with her at this time is not something that works,” an insider close to Affleck claimed to People. “He will date in the future, but for now his focus is on his sobriety, family, and his next project.”

After months of dating rumors, Affleck went public with yet another co-star, Ana de Armas. The two met on the set of Deep Water in 2019, and in March 2020, fans learned the co-stars were officially an item after they were reportedly spotted kissing in an airport following a getaway to Cuba. The pair went on to date for nearly a year before their breakup was announced in January 2021... and just a few months later, Affleck was sparking rumors with his old flame J.Lo.