The Ben Affleck dating list: The actor's romantic timeline, including J-Lo, Jennifer Garner and Ana de Armas
Actor Ben Affleck has been busy since splitting from Jennifer Garner - he's spoken out about their relationship and has since moved on with a co-star.
Page Six reported in March of 2020 that Affleck had a new romantic interest after he was spotted in Cuba with his co-star Ana de Armas.
After five months of publicly dating, De Armas shared an adorable selfie of the pair on her Instagram account showing just how loved up they are.
The stars play husband and wife in the upcoming psychological thriller, Deep Water.
De Armas, 32, is best known for her role in Knives Out. She's also set to appear in the upcoming James Bond film No Time To Die.
The couple has since quarantined together in California and are seen regularly taking walks with Affleck's dog and enjoying their Dunkin Donuts iced coffees.
They took things to the next level by taking a lavish vacation together to Joshua Tree in April to celebrate Ana's birthday.
The Knives Out star shared an album of photos on her Instagram including a selfie with Affleck alongside the caption "Thank you all so much for the birthday wishes and love! Cheers to another great year."
Affleck’s list of ex-lovers might not be as long as his A-list peers (unlike Leo, he appears to be a long term kind of guy) but he has dated a high profile set of actresses and singers.
After dating Gwyneth Paltrow for three years and getting engaged to Jennifer Lopez in 2002, he eventually settled down with Jennifer Garner, who he was famously married to for 12 years.
Of course, his most famous relationship might be a platonic one - he and fellow actor Matt Damon are known for their bromance ever since they took Hollywood by storm with Good Will Hunting. The two are still best friends to this day, in June Damon was seen leaving Affleck's Los Angeles home.
Here’s a look back at his most infamous relationships, from his Gigli years to his long-term relationship with Garner.
The Gwyneth Paltrow years
Actress Gwyneth Paltrow was Affleck’s first A-list girlfriend. They met at a dinner party thrown by Harvey Weinstein in 1997.
The famous co-stars started dating soon after Paltrow ended her engagement to Brad Pitt.
“I just think we have a very different sort of value system,” Paltrow told Diane Sawyer about why her relationship with Affleck didn’t work out. They dated from 1997 until 2000, starring alongside each other in Shakespeare in Love in 1998 and Bounce in 2000.
In a 2015 interview with Howard Stern, Paltrow did say that she and Affleck have remained friends to this day. “I like him,” she told Stern, “I’m still friends with him.”
The Gigli days
When Affleck dated Jennifer Lopez their high profile romance became one of the most talked about and memorable relationships of the early aughts.
The co-stars-turned-lovers were one of the first major relationships of the tabloid era and were one of the first celebrity couples to receive a mashed up moniker: “Bennifer.”
Lopez poked fun at the tabloid’s obsession with the relationship in her 2002 music video for 'Jenny From The Block.' The video is filmed from camera angles intended to emulate paparazzi perspectives and at one point in the video, Lopez and Affleck are seemingly spotted by cameras while canoodling on a yacht.
The pair met in 2002 while filming the rom-com Gigli, which was widely panned with several one star reviews. It's currently sitting pretty with a six percent score on Rotten Tomatoes.
Affleck famously proposed to Lopez with a 6.1 carat pink diamond ring from Harry Winston. They quickly got engaged and were planning to wed in September of 2003, but one week before their wedding date, Bennifer postponed their wedding “due to the excessive media attention.” In early 2004, Lopez confirmed to the media that she had called off the engagement.
Paltrow spoke to Diane Sawyer about the demise of his relationship with Lopez. “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,” she told Diane Sawyer.
Lopez opened up to People Magazine in 2016 about the much-publicized relationship, saying, "I think different time different thing, who knows what could've happened, but there was a genuine love there."
His decade-long marriage to Jennifer Garner
Jennifer Garner met Ben Affleck on the set of Pearl Harbor in 2000. The two weren’t romantically linked until fans saw their onscreen chemistry in Daredevil in 2002.
In October of 2004, just nine months after his very public break up with J-Lo, Affleck was seen out with the Alias actress at a Boston Red Sox World Series Game.
During Garner’s 33rd birthday party celebration at her home in Brentwood, Affleck proposed with a 4.5 carat Harry Winston ring.They were married in 2005 in a private ceremony in Turks and Caicos.
In 2005, the Daredevil co-stars welcomed their first child - a daughter named Violet, followed by daughter Seraphina in 2009 and their son Samuel in 2012.
They were together for 10 years, separating in 2015 and divorcing in 2017. There were rumors that Affleck cheated on Garner with their nanny, but he denies the claims to this day.
Speaking to Vanity Fair after their divorce, Garner said that Affleck was the love of her life. “What am I going to do about that? He’s the most brilliant person in any room, the most charismatic, the most generous. He’s just a complicated guy. I always say, ‘When his sun shines on you, you feel it. But when the sun is shining elsewhere, it's cold.' He can cast quite a shadow.”
The actor recently opened up to The New York Times about how his rocky relationship with alcohol ruined his marriage, saying, “I drank relatively normally for a long time. What happened was that I started drinking more and more when my marriage was falling apart. This was 2015, 2016. My drinking, of course, created more marital problems.”
He went on to say "the biggest regret of my life is this divorce," and explain “It’s not particularly healthy for me to obsess over the failures — the relapses — and beat myself up."
The SNL writer rebound
Two years after his divorce, Affleck found love again with Saturday Night Live writer Lindsay Shookus.
They were first photographed together during a July 2017 trip to London where Affleck was doing reshoots for the Justice League.
Throughout 2017, the couple was photographed together in Los Angeles and New York City, but Affleck also took her on a romantic trip to Maine a month after they were seen together in London.
In an interview with Elle, Shookus opened up about the public attention. “My entire career has been behind the camera, and that’s definitely where I’m most comfortable. I’m a producer, I’m a mom, a friend. Being considered a public figure honestly makes me laugh,” she explained.
A bit over a year after Shookus and Affleck became official, Affleck was spotted having dinner with 22-year-old model Shauna Sexton. He went on to date the model for two months.
Come February 2019, Shookus and Affleck were seen walking the streets of Manhattan hand-in-hand again. Their relationship appeared to be rekindled for only a short time, as a source told People in April that the two were no longer together, saying, “She has a kid and an ex-husband and a job in New York and Ben has his family and a job in L.A. and while they love and respect each other they just realized it wasn’t going to work. They really gave it another solid try.”
Since then, he’s kept a low-profile, despite being photographed with Jobs. Nixing rumors the pair were on a date, a source told Page Six that they’re just friends and that Jobs is dating celebrity chef Daniel Humm of Eleven Madison Park.
