A Timeline Of Ben Affleck's Relationships

This feature references alcohol misuse and addiction. 

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 on 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. Discussing the offending tattoo, Affleck initially told Extra that, "[It was] fake for a movie." (Reader, it wasn't.)

Affleck's love life came full circle after he made his way back to Jennifer Lopez. He is now married to the singer, but it took him a long time to get there. Let's take a look at the timeline of Ben Affleck's relationships.

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. Rothman isn't a public figure, exactly. But she did briefly give it a go as a Hollywood director-producer. She made a single comedy short film, the plot summary of which is listed on IMDb as, "Two wet-behind-the-ears buddies 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."

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." 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. 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.

Ben Affleck and Gwyneth Paltrow met at a dinner party in 1997 thrown by the now-disgraced producer Harvey Weinstein. At the time, the Oscar-winner was coming off her split from Brad Pitt and had started working with Affleck on "Shakespeare in Love." Although she'd later accuse the former producer of sexual harassment (he denied the allegations, per Deadline), during an episode of "The Howard Stern Show" (via The Wrap) she claimed that he had played matchmaker for her and Affleck — with whom she split in 2000. While Paltrow praised her former boyfriend for his smarts and sense of humor, she also suggested that their relationship may not have been the most enjoyable. "[He] wasn't in a good place in his life to have a girlfriend," she griped.

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" (via ABC News), the Goop entrepreneur commented on her ex's aborted engagement to Jennifer Lopez 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 served a gem of a response in describing who she thinks his perfect partner would be, saying, "Anyone that serves cold beer in a bikini."

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 an 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, "I really 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 due to the intense media glare. "When we found ourselves seriously contemplating hiring three separate 'decoy brides' at three different locations, we realized that something was awry," the couple shared in a joint statement published by People. In the end, the couple split in 2004 but stayed friends ... more on that later

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. However, two years later, the pair 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 a year later on Garner's 33rd birthday and they wed in a private ceremony later that year before welcoming 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, she 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. "The biggest regret of my life is this divorce," he told The New York Times. Later, he admitted, "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).

Ben Affleck clearly gave the Hollywood power couple thing a solid go — and it's understandable. Many celebrities and apparent 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. Interestingly though, a source told Us Weekly 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 for good.

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 (and 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.

Days after the actor 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 looked genuinely happy and Affleck looked a little less bright-eyed. Immediately following the excursion, a source claimed to People (via The Sun) 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.

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 reportedly listed her Venice, California home for sale, 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! News 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." Although the relationship was said to be "complicated," the source noted that the split had been mutually agreed upon and without any drama. "Ana doesn't want to be Los Angeles based and Ben obviously has to since his kids live in Los Angeles." Regardless, de Armas has since cleansed her Instagram feed of any evidence of the relationship. So, read into that what you will.

Just before Jennifer Lopez's split from Alex Rodriguez, her ex Ben Affleck mused to InStyle, "She remains ... the hardest-working person I've come across in this business." Amusingly, he addressed his finest compliments directly toward J. Lo, quipping, "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 exclusive, membership-only dating app Raya. The site has also hilariously been called Illuminati Tinder since only the most elite and connected singles are invited to mingle there.

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 as a caption before playing Affleck's clip. In the video, he says with a wry smile, "Nivine, why did you unmatch me? It's me!" As E! News pointed out, none of this is exactly verified, so we should probably take this rumored match with a grain of salt.

Ben Affleck and Jennifer Lopez found their way back into each other's lives in 2021. The couple sparked dating rumors after they were spotted out and about together on several occasions. At first, things seemed friendly. But it became clear that the celebs were once again in a relationship after Lopez shared an Instagram photo of her and Affleck kissing on her birthday.

Things moved quickly for the couple, perhaps because of the long history they already shared. They continued to express their love for one another publicly by walking red carpets together. Lopez even spoke about their relationship in an interview with People in 2022. "It's beautiful the way it feels very different than it was years ago," she said. " ... There's more of an appreciation and a celebration for it, which is nice."

The pair announced their engagement in April 2022, and a Las Vegas wedding followed in July 2022. Writing about the event for her "On The J Lo" newsletter (via Us Weekly), the "Hustlers" star wrote, "[The wedding was] exactly what we wanted. Last night we flew to Vegas, stood in line for a license with four other couples, all making the same journey to the wedding capital of the world." The husband and wife went on to spend their Honeymoon in Paris, and they both even brought their kids along with them.