All about the star's romantic ups and downs

By Michael Miller and Jodi Guglielmi
July 07, 2017 04:00 PM

Ben Affleck‘s love life is once again heating up.

Three months after Affleck and Jennifer Garner officially filed for divorce, the actor has started dating Saturday Night Live producer Lindsay Shookus.

“They are spending time together in L.A. Lindsay is staying at Ben’s new house,” a source tells PEOPLE of the duo, who stepped out together in Los Angeles Thursday night.

Multiple sources have told PEOPLE that their romance began in 2013 while Affleck was still married to Garner, but a source close to Affleck and Garner refutes that.

“They did not date while either of them were married,” the source maintains. Affleck and Shookus “started dating when they were separated.”

But before his latest romances, Affleck was one of Hollywood’s most eligible bachelors – and his ties with A-list beauties made headlines.

Here’s a look at some of the actor’s most famous past loves.

Gwyneth Paltrow

When Affleck rose to stardom after winning his first Oscar for Good Will Hunting in 1997, the Boston native was in a relationship with high school girlfriend Cheyenne Rothman, with whom he still keeps in touch.

But the actor soon began dating Gwyneth Paltrow after meeting her at a dinner thrown by studio mogul Harvey Weinstein. The pair went on to costar in the movies Shakespeare in Love and Bounce.

The couple shared quick wit and a wicked sense of humor – but their relationship had its share of ups and downs. In January Paltrow told Howard Stern that while dating Affleck was fun, her parents did not approve.

“He’s super intelligent and really, really talented and he’s funny,” she said. “But he wasn’t in a good place in his life to have a girlfriend.”

At the time they were dating, Paltrow was little more blunt about his love of a good time. Teasing him on Good Morning America, she joked his perfect woman was “anything that serves cold beer in a bikini.”

Still, they clearly enjoyed one another’s company. The pair broke up in 1999, but briefly reunited before finally ending things in 2000.

But the GOOP mogul and Affleck remain pals. “I like him,” she told Stern. “I’m still friends with him.”

Jennifer Lopez

Two years after breaking up with Paltrow, Affleck met Jennifer Lopez on the set of the mobster comedy Gigli, and the super couple known as Bennifer was born.

The film went on to be one of Hollywood’s most famous flops – and the pair’s second movie together, 2004’s Jersey Girl, also tanked at the box office. But their off-screen relationship became a tabloid blockbuster.

The two stars got engaged in 2002 – Affleck gave Lopez a $2.5 million diamond engagement ring. He also underwent a makeover, ditching facial scruff and flannel shirts for slicked-back hair and Versace suits.

But perhaps the most infamous moment in the couple’s high-profile relationship was Lopez’s “Jenny from the Block” music video, which featured Affleck in a tank top and shades as he massaged suntan lotion on the bikini-clad diva in a sequence the actor would live to regret.

“In our culture, we get very much into short-handing people,” Affleck told Details in 2012. “And I got shorthanded as ‘that guy’: Jennifer Lopez, movies bombed, there he must be a sort of thoughtless, dilettante, solipsistic consumer, blah, blah, blah.”

The pair planned to wed in an elaborate ceremony in Santa Barbara, California, on Sept. 14, 2003, but Affleck called off the festivities with four days’ notice because of “excessive media attention.”

The couple officially announced a split a few months later. Affleck later called his year in the media glare as Lopez’s fiancé his “annus horribilis.”

“I don’t think I had ever been heartbroken in that way before,” she later told VH1. “I had so many hopes and dreams on something.”

Still, they found a way to make peace. Affleck told The Hollywood Reporter that he and the pop superstar occasionally “touch base,” and Lopez warmly congratulated Affleck when he won his Golden Globe for Argo in 2013.

“I respect her,” he told THR. “I like her.”

Ben Affleck Is ‘Devastated’ Over Divorce, ‘Really Tried to Save Their Marriage’: Source

Jennifer Garner

In the same interview, the star praised his wife, Garner, whom he began dating not long after the pair starred together in the action movie Daredevil in 2003.

“She truly is kind,” he said. “She means no one any harm. She doesn’t have ill will for any person. She’s not competitive with other people. She’s not spiteful.”

But after 10 years of marriage and three children, Affleck’s relationship with the woman who once described him as her “soul mate” also foundered.

Said a Garner source: “They are two very different people.”

Both Affleck and Garner have made cooperative co-parenting a priority since they separated in 2015 and officially filed for divorce this past April. They also continue to spend time together as a family.

“They are working hard to continue to build a world that is right for their children,” a source previously told PEOPLE. “They spend quite a bit of time on this. They continue to co-parent and respect each other. I think some would be surprised to see how close their relationship remains.”