After Jennifer appeared as a guest star on Felicity, she and actor couldn’t help but grow strong feelings for each other. The duo ended up making it official by exchanging their vows in October 2000. They were married for three years before getting separated. By March 2004, their divorce was finalized. 

In hindsight, the actress said she would have reconsidered getting hitched. “Everyone reaches maturity at different times. I wish I’d known to wait for marriage until I was 30 or over,” Jennifer told The Sun. “I did marry in my twenties and I found divorce a crushing experience. I thought the divorce statistics would never apply to me. I was beyond heartbroken when they did.”

Rumors Jennifer and actor were swirling the duo were an item in real life after they costarred together on Alias. By August 2003, the Ghost of Girlfriends Past star’s rep confirmed the speculation was true to Us Weekly, following her split from Scott. Although they didn’t work out romantically, Michael said they remained “best friends” after during an interview with USA Today in 2005. 

In November 2023, Jennifer confirmed that her and Michael’s friendship was still going strong when she wished him a happy birthday. “I can’t remember why I was Bavarian, but I do know today is your birthday. I hope it’s a great one, Michael! XX S. Bristow,” she wrote alongside a photo from their Alias days.

When fans watched Pearl Harbor, they quickly began rooting for and Jennifer to get together. It wasn’t until 2004 — after they appeared together on Daredevil — they went public with their romance. The Gone Girl actor popped the question in April 2005, and they became husband and wife only two months later.

The dynamic duo welcomed their first daughter, Violet, in December 2005, and child Seraphina “Fin” in January 2009. Their son, Samuel, was born in February 2012. 

People were devastated when the pair announced they were breaking up in 2015. “We go forward with love and friendship for one another and a commitment to coparenting our children whose privacy we ask to be respected during this difficult time,” they shared in a statement after their 10-year anniversary.  

Jennifer and Ben’s divorce was officially finalized in October 2018, and he later admitted their divorce was his “biggest regret” in a February 2020 interview with the New York Times.

The actress “was surprised” by the revelation, a source told In Touch exclusively afterward. “She was touched by his honesty. She’s impressed he’s taken ownership of his mistakes and sees it as a sign that he’s made huge progress.”

Ben and Jennifer sparked rumors they might be getting back together after the duo was photographed smiling and laughing at son Samuel’s 13th birthday party at a paintball range on March 2, 2025, in pictures obtained by The Daily Mail. The Air star even playfully put his arm around his ex-wife’s waist as she fired her paintball gun, in a video obtained by TMZ.

“It’s no secret that Ben’s relationship with his ex is better than ever. Ben and Jen haven’t had this many laughs or been this comfortable with each other in years,” a source exclusively told In Touch on March 5, 2025. “It’s like they’re newlyweds again, except it’s nothing like that. They’ve developed a true friendship.”

The insider added, “They not only like each other again, but Jen respects and trusts him with her life. They’ve come a long way and been through a lot.”

Businessman and Jennifer’s romance was revealed in 2018, and they seemed to be quite happy together with their shared interests. She was often beaming with delight in photos captured during their romantic date nights.

The lovebirds parted ways in August 2020, but it sounded like there was a chance for the exes to give their love another go down the line. “Jen and John remain on friendly terms so there’s a possibility that they could rekindle their relationship in the future, but right now it’s over,” an insider told In Touch at the time.

By May 2021, they were back together, Us Weekly confirmed. “It started up a few weeks ago.”

After giving love another shot, Jennifer and John continued to keep their relationship out of the spotlight. A source exclusively told In Touch in April 2022 that John is “not about the public display just because it’s what everyone else does” and Jen “totally respects” his decision.

In January 2023, a source told Us Weekly that while Jen already began seeing a “long-term future” with her beau, she nevertheless wasn’t “in a hurry to rush down the aisle just yet.”

After the photos of Jen and Ben being playful at their son’s birthday party emerged in 2025, a source exclusively told In Touch, “She’s in love with John.” The insider continued, “Of course John gets a ton of questions from his friends about Jen and Ben’s relationship, some even think he should be worried. Most men wouldn’t be thrilled to see their girlfriend in an intimate embrace with her ex, but John knows the truth.”

“He knows Jen is loyal to him and can also be there for the father of her children. That’s just who Jen is. It’s not for everyone, but John is very confident in what he has with Jen. He’s not concerned,” the insider added about the Hollywood star’s longtime boyfriend.