A Timeline Of Ben Affleck's Relationships

In 2016, while reeling from the biggest breakup of his life at age 44, Ben Affleck got himself into genuine superhero shape for his turn as Gotham's dark knight in "Batman v Superman: Dawn of Justice." Unfortunately, the film pulled a putrid 29% critics aggregate via Rotten Tomatoes, and as a talented director himself, Affleck probably knew he'd made a dud. Still, he dutifully hit the junkets with co-star Henry Cavill, but just couldn't seem to summon the enthusiasm. And thus, one of the greatest memes of all time was born: Sad Affleck.

Behind the cowl and scowl, there always seemed to be more to this particular movie star than what meets the eye. Whether the six-foot-four Hollywood actor is taking the most defeated drag of a cigarette ever captured by paparazzi or unveiling a shockingly enormous (mid-life crisis?) back tattoo, his romantic life has appeared to feature a well of ennui that runs just as deep as any boo-hoo Bruce Wayne backstory. Affleck initially told Extra that the tat was "fake for a movie." (Reader, it wasn't.) And his most serious ex, Jennifer Garner, had her own folksy take, telling Vanity Fair, "You know what we would say in my hometown about that? 'Bless his heart.' A phoenix rising from the ashes. Am I the ashes in this scenario? I take umbrage. I refuse to be the ashes." Don't we all. 

Let's resurrect the burnt crisps of Ben Affleck's many relationships and find out exactly how they seemingly caught fire in the first place.

Ben Affleck's first love was a filmmaker, too

There's nothing quite like that first love. Ben Affleck's earliest-known romance started in 1990, when he met his high school sweetheart, hometown girl Cheyenne Rothman, at a summer camp, according to PopSugar. Rothman isn't a public figure, exactly. But she did briefly give it a go as a Hollywood director-producer. She made a single short film comedy, which IMDb summarizes as being about "two wet-behind-the-ears buddies [who] go looking for the crack rock explosion." The 2004 flick has the cheeky title, "Release the Cracken," instead of Kraken (get it?). Unfortunately, we defy you to find a trailer or even a clip of this movie.

Affleck and Rothman called it quits in 1997, the same year the actor blew up into a genuine movie star 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, mostly minus scores of sordid flings in between, would start his dating life with a ship that lasted as long as Brad Pitt was stranded in "Tibet" (fun fact: that film was also released in 1997). 

For her part, Rothman would also get a consolation prize: a succinct "thanks" in the credits for Affleck's Oscar-winning film, which was also released that same formative year: a little movie called, "Good Will Hunting."

He and Matt Damon have life-long chemistry

Ok, so this isn't a romantic relationship, but try and tell us that Hollywood's most famous and enduring modern bromance isn't a form of relational love. Ben Affleck and Matt Damon were childhood friends — and, as the latter told ET in 2016, it was their mutual cinephilia that bonded them. "We were both in love with the same thing — acting and filmmaking," Damon explained. "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," according to IMDb. 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 Variety, which said they were going to get $600,000 from the film, as zero-down collateral to rent an apartment, per US Weekly. Somehow, the landlord agreed. 

Damon and Affleck remain close friends to this day and can even be spotted on double dates on the rare occasions that Ben meets someone he deems Matt-worthy.

Was Ben Affleck repeatedly shaded by ex Gwyneth Paltrow?

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 starting working with Affleck on "Shakespeare in Love." 

As Paltrow told Howard Stern of her Oscar-winning turn in 2015 (via The Wrap), 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 "intelligent and funny," she also told Stern that the future Batman actor "wasn't in a good place in his life to have a girlfriend."

But this wasn't the first time that Paltrow seemingly dropped some not-so-subtle dirt about Affleck. During a 2003 interview with Diane Sawyer on "Good Morning America," the Goop entrepreneur commented on her ex's aborted engagement to Jennifer Lopez (via Entertainment Weekly), and hinted that Affleck was the engineer of his own relationship issues. "I just think we have a very different sort of value system," 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." Paltrow also added this gem, per E!: alleging that Affleck's perfect partner would've been "any sort of stripper at Scores. Anyone that serves cold beer in a bikini."

Inside Ben Affleck's relationship with Jennifer Lopez

You can almost feel bad for celebs who fall in love on set. Between the long work days and being away from family and friends, even if it's not the right fit, pretending to be in love for the cameras can easily bleed into unscripted and 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 vibed with Affleck right away, telling People in 2016 that she "felt like ... 'Okay, this is it.'" The movie itself was a spectacular bomb, critically and commercially, but "Bennifer" was born, and a media frenzy ensued. "We just happened to be together at the birth of the tabloids," an emotionally honest but factually fallacious Lopez mused. "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," per People. The paparazzi madness was so intense that they were "seriously contemplating hiring three separate 'decoy brides' at three different locations." In the end, the couple split in 2004, but stayed friends. Much more on that later, so keep scrolling for the old circle back.

Ben Affleck and Jennifer Garner sealed the deal

Ben Affleck and Jennifer Garner actually met while filming "Pearl Harbor" in 2000. But this relationship didn't start right off the bat, as Garner was still married to actor Scott Foley, according to Insider. 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, according to People, and they wed in a private ceremony later that year and 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 "getaway." The mag also claimed that he was dating the nanny, but Affleck's rep called foul: "The story is complete garbage and full of lies ... We are considering legal options." Regardless, within a month, 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," while further admitting 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."

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

The actor stayed up late for Saturday Night Live producer Lindsay Shookus

Ben Affleck clearly gave the Hollywood power couple thing a solid go — and it's understandable. Many celebrities and "experts" have spoken about the difficulty of dating someone who doesn't understand the scrutiny of superstardom, so maybe we, as fans, can put away our tiny violins and take this observation seriously.

But in 2017, Affleck switched up his M.O. when he went public with Emmy Award-winning "Saturday Night Live" producer Lindsay Shookus, according to US Weekly. Interestingly though, a source told the mag that the relationship wasn't new at all, 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."

The two were consistently spotted out by paps while dining and grabbing coffee over the next year. However, in August 2018, Affleck was seen on a date with Playboy model Shauna Sexton (more on that below), and Shookus' Instagram feed was suddenly (and temporarily) deleted. A few days later, it was reported that the couple's romance was over, with a source alleging to US Weekly that the whole thing had been "tumultuous." 

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."

Ben Affleck 'casually' dated model Shauna Sexton

At this point, Ben Affleck gives the impression of a man who loves hard, gets bored around the two-year mark, and then strays into the next fling. "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," he told The New York Times in 2020. "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."

In other words, Affleck's dating life may be relatable as heck to some. 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 (24 years the actor's junior), 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, per People.

Days after Affleck exited the clinic in October, he and Sexton took a rugged trip to Montana, during which he even made his debut on the model's Instagram: Sexton looks genuinely happy; Affleck looks a little less bright-eyed. Immediately following the excursion, a source claimed to People that their "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." Ouch.

The movie star wooed Ana de Armas

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, as it's possible the duo met while filming "Deep Water." They later were spotted kissing during reshoots that November, and by the following month, the "Bladerunner 2049" star had listed her Venice, California home for sale, People reports, and moved into Affleck's Pacific Palisades pad. 

The whirlwind romance was documented in endless PDA moments. De Armas hung out with Affleck's kids. The two even went extremely Instagram official, with Affleck cheesing his hardest. Not to mention, De Armas also got to meet Affleck's longtime pal, Matt Damon, and was reportedly helping her famous beau stay sober. "Since Ana has been in Ben's life, being sober has become easier to manage ... Drinking isn't part of the equation with Ana," a source cited by E! explained. Then, suddenly, in January 2021, it was all over. 

"Ben is no longer dating Ana," another insider claimed to People. "She broke it off." Describing the relationship as "complicated," the source noted that the split was "mutual" and "amicable," adding, "Ana doesn't want to be Los Angeles based and Ben obviously has to since his kids live in Los Angeles." Still, try looking at photos of their year together and not getting a little weepy.

Bennifer 1.0 fans rejoiced at Ben Affleck and Jennifer Lopez's reunion

With Ana de Armas out, was Ben Affleck craving the familiar comfort of an old flame? To be fair, it seemed as though one Jennifer Lopez had her own reasons to run back to the actor, too. Although, it should be noted that this celeb reunion appears to be platonic, as of this writing.

In mid-April 2021, J. Lo called off her engagement to former baseball star Alex Rodriguez and split with the slugger for good, according to People, releasing a boilerplate statement about being "better as friends" and the obligatory, "We wish the best for each other." However, sources cited by the mag claimed that the breakup was a "long time coming." Indeed, cheating rumors 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 were a sign as ominous as it seemed. 

Two weeks later, Affleck was spotted getting into Lopez's white Escalade and chauffeured to her Los Angeles mansion, per Page Six. The two weren't actually spotted together, but a source claimed to the outlet that "security picks him up at a nearby location and drops him off after spending a few hours at her house." The OG "Bennifer" reportedly hung out three times around this time, with an insider noting, "They are friends ... they've never not been."

Ben Affleck reportedly hit the dating app scene

Just before Jennifer Lopez's split with Alex Rodriguez, ex Ben Affleck mused to InStyle that the superstar is "the hardest-working person I've come across in this business." He amusingly directed toward J. Lo, "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 elite and connected singles are invited to mingle.

Affleck allegedly matched with Nivine Jay, who quickly deleted him, assuming it was a catfish. He then reportedly sent her a video proving it was him, and she made a viral TikTok video about the whole debacle that May. "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 wrote, before playing Affleck's clip. "Nivine, why did you unmatch me? It's me!" Affleck says in the video with a wry smile. 

However, as E! points out, none of this is exactly verified, so we should probably take this rumored Ben Affleck relationship with a grain of salt.