Ben Affleck has faced his fair share of highs and lows over the years. Over decades in the
spotlight, the actor and filmmaker has worked hard on sobriety, making movies and, of course,
finding love. Here's the timeline of Ben Affleck's most high-profile relationships.
There's nothing quite like that first love. Thankfully, most people's first relationships
don't end up like Romeo and Juliet which, if you didn't already know, didn't turn out
well.
Movie star Ben Affleck's earliest-known romance didn't start out in tinseltown. It was in
Boston 1990 when he met his high school sweetheart, hometown girl Cheyenne Rothman, at a summer
camp.
Affleck and Rothman called it quits in 1997, the same year the actor blew up into a genuine
movie star after the release of Good Will Hunting, and started dating Gwyneth Paltrow
— draw your own conclusions there.
So yes, the man who would go on to hop from one serious partnership to another would start
his dating life back home, naturally, with someone he had known for several years.
For her part, Rothman would also get a consolation prize: a "thanks" in the credits for Affleck's
Oscar-winning film, Good Will Hunting.
Just try and tell us that Hollywood's most famous and enduring modern bromance doesn't
belong on this list. Ben Affleck and Matt Damon were childhood friends — and, as Damon
told ET in 2016, it was their mutual love of cinema that bonded them together.
Damon explained:
"We were both in love with the same thing — acting and filmmaking. I think we fed
on each other's obsession during really formative, important years and that bonded us for life."
The two also come from humble beginnings. In 1992, after they got their first decent
paychecks while co-starring in the film, School Ties, the duo quickly blew all the cash and
had to bounce around Los Angeles while they penned their breakout hit Good Will Hunting.
Even as the film for which they eventually won matching Oscars was hitting movie theaters,
the friends were so broke that they had to use a copy of the Variety, which said they
were going to get $600,000 from the film, as zero-down collateral to rent an apartment.
From there, they developed their careers in showbiz side by side.
Damon and Affleck remain close friends to this day.
Ben Affleck and Gwyneth Paltrow met at a dinner party in 1997 thrown by the now-disgraced
producer Harvey Weinstein. At the time, Paltrow was coming off her split from Brad Pitt and
had started working with Affleck on Shakespeare in Love.
As Paltrow told Howard Stern of her Oscar-winning turn, Weinstein — whom she later accused
of sexual harassment — had oddly played matchmaker:
"At the time, [Weinstein] was trying to put all of his people in all of the movies."
Though Paltrow graciously praised Affleck, with whom she split in 2000, as being "intelligent
and funny," she also told Stern that the future Batman actor, quote, "wasn't in a good place
in his life to have a girlfriend."
This wasn't the first time that Paltrow dropped some not-so-subtle dirt about Affleck. The
Goop entrepreneur once told Good Morning America about her ex's aborted engagement to Jennifer
Lopez, and hinted that Affleck was the engineer of his own relationship issues.
She said:
"I just think we have a very different sort of value system. 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."
Paltrow also alleged that in her opinion, Affleck's perfect partner at the time would've
been:
"[...] any sort of stripper at Scores. Anyone that serves cold beer in a bikini."
You can almost feel bad for celebs who fall in love on a movie set. Between the long work
days and being away from family and friends, pretending to be in love for the cameras can
easily bleed into unscripted -- and sometimes disastrous -- reality.
That seems to be the case with Ben Affleck and Jennifer Lopez, who met on the set of
Gigli in 2002.
J. Lo was married at the time to her second husband, Chris Judd, but seemed to hit it
off with Affleck right away regardless. As a movie, Gigli was a bomb both critically
and commercially. But it did give rise to "Bennifer," and a media frenzy ensued.
Lopez said:
"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."
Affleck went big in November 2002 with a custom-made Harry Winston pink-diamond solitaire engagement
ring. The two set a wedding date for September 2003, but postponed the ceremony just one
day before the nuptials, citing excessive media attention as their reason for delaying
the marriage.
The paparazzi madness was so intense that they reportedly considered hiring decoy brides
to distract the press at three different locations. The couple split in 2004, but remain friends
-- maybe even close friends -- to this day.
Ben Affleck and Jennifer Garner met while filming Pearl Harbor in 2000. But their romantic
relationship didn't start right off the bat, as Garner was still married to actor Scott
Foley.
Two years later, however, Affleck and Garner teamed up again for Daredevil. Affleck, who
was still dating Jennifer Lopez, may have been playing a blind superhero, but he still
had eyes for Garner, later admitting to Playboy that he fell in love with her on this set.
Ben and Jen 2.0 went public with their romance in 2004. He proposed in 2005 on Garner's 33rd
birthday, and they married each other in a private ceremony later that year. They now
have three children together.
However, trouble started in 2015 when Us Weekly reported that Affleck had taken the family's
nanny, Christine Ouzounian, to Las Vegas for a mysterious, and scandalous getaway. The
magazine also asserted that he was full-on dating the nanny, a claim which Affleck's
representative countered by saying:
"The story is complete garbage and full of lies [...] We are considering legal options."
Within a month, however, Affleck and Garner's divorce was announced.
In 2016, Garner told Vanity Fair that the couple had been split for months before the
alleged nanny incident. Meanwhile, Affleck blamed himself for the failure of the marriage,
which he called the biggest regret of his life.
He further admitted to The New York Times:
"I started drinking more and more when my marriage was falling apart [...] My drinking,
of course, created more marital problems."
Ben Affleck gave the Hollywood power couple thing a solid go for several relationships,
and even though the tabloids were all over him for it, it's understandable why. Many
celebrities have spoken about the difficulty of dating someone who doesn't understand the
scrutiny of superstardom.
But in 2017, Affleck switched up his patterns when he went public with Emmy Award-winning
Saturday Night Live producer Lindsay Shookus. Interestingly though, a source speaking to
Us Weekly said the relationship wasn't new, claiming:
"Ben and Lindsay started their affair about three years ago, just a few months after she
became a mom. They were not casually dating — they were having a full-blown affair."
However, in August 2018, Affleck was seen on a date with Playboy model Shauna Sexton.
A few days later, it was reported that Affleck's romance with the Saturday Night Live producer
was over.
For her part, Shookus had hinted to Elle earlier that year that she wasn't made for the spotlight,
explaining:
"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."
At this point, Ben Affleck gives the impression of a man who starts a relationship, gets bored
around the two-year mark, and then strays into the next fling. That assessment may not
be far off.
Speaking in an interview with The New York Times in 2020, Affleck said:
"People with compulsive behavior, and I am one, have this kind of basic discomfort all
the time that they're trying to make go away. You're trying to make yourself feel better
with eating or drinking or sex or gambling or shopping or whatever. But that ends up
making your life worse […] It becomes a vicious cycle you can't break."
Enter Playboy model Shauna Sexton in 2018, when Affleck was still, as far as anyone knew,
involved with Saturday Night Live producer Lindsay Shookus.
Only 22 years old at the time, Sexton and Affleck first got together at Los Angeles
eatery Nobu on August 16, but hit a snag when Affleck checked into rehab shortly after.
When he checked out, Affleck took Sexton to Montana — but soon after a source claimed
to People that their so-called "casual" relationship was done:
"He enjoyed being with her but is working on himself, and being together with her at
this time is not something that works."
Ben Affleck and Ana de Armas were first spotted together in Havana in March 2020. De Armas
is native to Cuba, perhaps suggesting the affair was already underway at the time they
were first spotted. It's possible the duo met while filming the movie Deep Water.
They later were spotted kissing during reshoots that November, and by the following month,
the Blade Runner 2049 star had listed her Venice, California home for sale, and moved
into Affleck's place in Pacific Palisades.
The whirlwind romance was documented in many public displays of affection. De Armas was
seen hanging out with Affleck's kids, and the two even went extremely Instagram official.
Not to mention, De Armas also got to meet Affleck's longtime pal, Matt Damon, and was
reportedly helping her famous beau stay sober.
One source cited by E! explained:
"Since Ana has been in Ben's life, being sober has become easier to manage [...] Drinking
isn't part of the equation with Ana."
Then, suddenly, in January 2021, it was all over. An insider told People:
"Ben is no longer dating Ana. She broke it off. Ana doesn't want to be Los Angeles-based
and Ben obviously has to since his kids live in Los Angeles."
Well, it was good while it lasted.
With Ana de Armas out of his life, was Ben Affleck craving the familiar comfort of an
old flame? Maybe. To be fair, it seemed as though Jennifer Lopez had her own reasons
to meet with the actor, too.
In mid-April 2021, J. Lo called off her engagement to former baseball star Alex Rodriguez and
split with the slugger for good, releasing a boilerplate statement about being, quote,
"better as friends."
Sources later claimed that the breakup was a long time coming. Rumors of cheating regarding
A-Rod had swirled for months, and Lopez admitted to Allure in February 2021 that the duo had
sought couples counseling.
But in the end, the power couple's twice-postponed nuptials turned out to be an ominous sign
of where things were going for the relationship.
Two weeks later, Affleck was spotted getting into Lopez's white Escalade and chauffeured
to her Los Angeles mansion, though the two weren't actually spotted together.
Lopez and Affleck reportedly hung out three times around this time, spurring even more
rumors, with an insider noting to Page Six,
"They are friends [...] they've never not been."
Just before Jennifer Lopez's split with Alex Rodriguez, Ben Affleck mused to InStyle that
his ex-girlfriend superstar is, quote, "the hardest-working person I've come across in
this business."
He amusingly directed toward J. Lo when he said:
"Where are you keeping the fountain of youth? Why do you look the same as you did in 2003
and it kind of looks like I'm in my 40s [...] at best?"
It's in that mindset that this A-list movie star reportedly had a near-miss with a TikTok
micro star. In 2021, the newly-single Affleck reportedly found himself on the dating app
Raya, which describes itself as:
"[An] online membership-based community for dating, networking, and making new friends."
The site has more aptly been called "Illuminati Tinder," where only the most elite and connected
singles are invited to mingle.
Affleck allegedly matched with Raya user Nivine Jay, who quickly deleted him, assuming that
the Ben Affleck account was just a fake. He then reportedly sent her a video proving it
was him. She made a TikTok video about the encounter, which went viral, that May.
She wrote on her post:
"Thinking of the time I matched with Ben Affleck on Raya and thought it was fake so I unmatched
him and he sent me a video on Instagram."
She then played Affleck's clip, in which he follows up with her while flashing his wry,
movie star smile.
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