Brilliant and charismatic? Complicated and shadow-casting? Let's see what
Ben Affleck's old flames have had to say about the talented — and troubled — actor.
Before Bennifer, Ben Affleck and Gwyneth Paltrow were Hollywood's "It" couple. The movie
stars met in 1997 at a party hosted by Harvey Weinstein, and dated on-and-off for three years,
according to Page Six. In that time, the celebs starred alongside each other in "Shakespeare In
Love" and "Bounce," apparently deepening their connection along the way. In 2003, Paltrow
addressed the breakup while being interviewed by Dianne Sawyer on "Primetime." She said,
"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."
Twelve years later, Paltrow gave more insight into her previous relationship
with Affleck during an interview with Howard Stern. She said at the time,
"He's super intelligent and really, really talented and he's funny. But
he wasn't in a good place in his life to have a girlfriend."
"I just… you know, I thought you looked a little lost."
"No, I'm fine. I think it was going pretty good up until now."
While Affleck may have not been the best boyfriend to Paltrow,
she made it clear that there were no hard feelings. In 2022, the Goop CEO had only
good things to say about her ex-boyfriend finding love again. During an Instagram Stories Q&A, a fan
asked her how she felt about Affleck reuniting with Jennifer Lopez, to which she responded,
"Love!!! So romantic!!! Very happy for them."
Ben Affleck and Jennifer Garner began dating shortly after he and Jennifer Lopez split
in 2004. They tied the knot just one year later and went on to have three children,
before announcing their divorce in 2015. Garner has addressed
the highly-publicized separation over the years, and she's been honest about
the struggles of co-parenting. Two years following their split, she told News.com,
"I would not have chosen this life for myself or for my kids. I would not choose
to be single or be in this position. It's something that we are working through."
The mother of three also opened up about what it was like to date Affleck,
and admitted that the actor had his flaws. While speaking with Vanity Fair in 2016, she revealed,
"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."
She also reminisced to the outlet on the good memories they shared and the
things that drew her to Affleck in the first place. Garner said,
"I ran down the beach to him, and I would again... He's the love of my life. What am I going to do
about that? He's the most brilliant person in any room, the most charismatic, the most generous."
Ben Affleck and Ana de Armas, his "Deep Water" co-star, sparked dating rumors
after they were spotted vacationing in Cuba together. The couple seemingly confirmed
their relationship in 2020 at the start of the COVID-19 pandemic when they were photographed
walking their dogs outside of Affleck's home every morning. The duo wasn't afraid to pack
on the PDA during these strolls, despite paparazzi snapping photos. Unfortunately,
this couple's chemistry wasn't enough to keep the relationship afloat.
"So what now? You wanna divorce?"
In 2021, People reported that the former co-stars had split. A
source told the outlet that de Armas initiated the breakup and alleged,
"Their relationship was complicated. Ana doesn't want to be Los Angeles based
and Ben obviously has to since his kids live in Los Angeles."
Meanwhile, another source claimed that the split was mutual and that the couple simply
realized they were at different points in their lives. De Armas herself set the record
straight during an interview with Elle, in which she revealed that the constant
media attention that surrounded their relationship was overwhelming. In fact,
it was so horrible that she ended up leaving L.A. entirely, moving to New York City instead.
Former Playboy model Shauna Sexton was only 22 years old when she was first spotted with
then-46-year-old Ben Affleck in 2018. Toward the end of Sexton's relationship with Affleck,
it was revealed that he had checked into rehab for alcohol addiction.
In a since-deleted Instagram post shared a little over a month later,
the actor revealed that he'd completed a 40-day treatment for alcohol addiction. He wrote,
"Battling any addiction is a lifelong and difficult struggle. Because of that,
one is never really in or out of treatment.
It is a full-time commitment. I am fighting for myself and my family."
When news of Affleck's hospitalization broke, Sexton came under fire for her past alcohol
use. According to People, social media users blamed the model for the actor's rehab stay.
Commenting on a since-deleted Instagram post, Sexton defended herself. Although she
admitted to having been arrested for underage drinking and public intoxication in the past,
she insisted that she did not drink in front of Affleck. Furthermore,
the model stressed that the actor was responsible for his own actions. She wrote,
"That being said, Ben is a grown ass man... He makes his own decisions. Blaming a 22-year-old
for someone's 3rd time in rehab is just ridiculous. He is human. I am human."
Ben Affleck's complicated love life came full circle when he reunited with his ex-fiancee,
Jennifer Lopez, in 2021. This rekindling may not have come as a surprise to those who
have noted the kind words the stars have shared about each other over the years,
even after they were no longer together. In 2016, Lopez reminisced to People about
the love she shared for Affleck. She said of the past relationship,
"I think different time different thing,
who knows what could've happened, but there was a genuine love there."
Six years later, Lopez told People that she'd watched her
ex-fiance's evolution from afar. She explained,
"To see the person, the human being, the man that he is today, the father that he is today,
the partner that he is — he is so everything I always knew he was and wanted to be."