There may not be just “one” person you’re meant to be with — and that’s totally okay! From the two famous Jennifers to other mysterious ladies, Affleck has dated some of the most gorgeous women in the industry!
A Bit About B.Affleck
Let’s start out with a little background on this Hollywood A-lister: first up, let’s talk about the big bucks! Ben Affleck is a pretty high-paid actor and is currently worth around $150 million. Sure, it’s about a tenth of what Kim Kardashian is worth, but gosh, it’s still a lot of money!
The actor, producer, director, and screenwriter has been in the business for over 30 years! You probably know him best from "Good Will Hunting" (which he wrote and starred in with his childhood buddy Matt Damon), "Armageddon," "Pearl Harbor," "Gone Girl," and his recent portrayal of Batman.
Let’s Talk About Love
Okay, fine, now for a bit more of the juicy bit; his love life. Let’s look at Ben Affleck’s timeline of lovin’ and the famous ladies he’s romanced over the years. You probably know two of them, but the others may be a surprise.
The first woman was his high school sweetheart, which seems to be a pretty common theme for many celebrities, having a long first relationship fresh out of high school and into college. Do you know who Ben Affleck's is?
First Love: Not a Woman?
Ben Affleck was born in California and was raised in Cambridge. His parents were always involved in the arts, and it was his mother who nudged him to try acting. When he turned eight, he met Matt Damon and the two are still friends today.
Not what you expected, eh? But this is bro-love, bromance…and it’s lasted for over 40 years. The two have gone on to co-star in many films, as well as write and direct together. We know they’ll keep at it. besides, if you make it after the first 10 years, you’re literally set for life!
Affleck and Damon: Bros Since Childhood
We like to think that these two just locked eyes, and Bam! Instant connection. But the truth is, their moms were integral in starting their friendship. The pair lived just blocks away from one another and also ended up at the same high school.
A fun anecdote that Damon revealed in an interview told how Affleck fended off a bigger kid that was picking on Damon. After helping him out (read: tackling the bully), Damon knew from then: “this is a good friend.” And through thick and thin, the pair have been with each other up to this very day.
Okay, Who Was the First Woman Then?
Alright, you got us. Let’s chat a bit about Affleck’s high school years and his first love, Cheyenne Rothman. The pair met as teenagers — you know, that summertime romance — and were romantically tied for a lengthy seven years.
It was his rise to fame in "Good Will Hunting" that most likely led to the split. Whether it was differences in growth or values or what they wanted, we’ll never know, but they were so young! Rothman went on to become a short-film director, and you know, as they say, you never forget your first relationship!
Shakespeare’s in Love
Affleck, where art thou Affleck? It doesn’t have the same ring to it, does it? Even when it’s Gwyneth Paltrow calling out from across the stage to her co-actor. So yes, you guessed it, Gwyneth Paltrow was the first leading lady with whom Ben Affleck had a relationship.
It’s rumored that Affleck broke up with Rothman and jumped straight into a relationship with Paltrow. Talk about quick. The pair dated for almost three years during which they co-starred in two films. Of course, one of the movies was "Shakespeare In Love," while the other was a film called "Bounce."
Bounce... To the Next Lady?
As you know, Affleck dated Paltrow between 1997 and 2000. They actually dated on and off over the course of the period, after Affleck first laid eyes on her at a dinner party. During the filming of "Bounce," Paltrow and Affleck got back together. However, this was short-lived.
So by the end of 2000, the pair had gone their separate ways. They did make quite a sweet couple together, but all isn’t fair in love and war! Do you know who’s next up on Ben Affleck’s love list?
Ben’s Therapy Stint
After his breakup with Gwyneth, Ben Affleck put himself into residential therapy to battle a drinking problem. We’re not sure if it was due to his relationship ending or the volatile nature of Hollywood and being in the industry, but we’re glad he had the sense to admit himself at the time.
For Affleck, though, his time in therapy wouldn’t be the last time he was there and would continue to battle the bottle over the course of his career. Less than two years later, he probably had no idea that he’d be engaged to a Hollywood beauty!
(J)Lo and behold, we arrive at our next leading lady who was charmed by Affleck. (Or maybe the other way around, we’re talking about Jennifer Lopez here!) Fans totally loved them as “Bennifer” after they met on the set of the film "Gigli."
The couple dated for two years, following Jennifer Lopez’s divorce from Cris Judd in 2002. Both Lopez and Affleck couldn’t keep away from one another, and things seemed not only steamy but very serious!
From Gigli to JLo
This highly stalked couple (literally though, we don’t think they got an ounce of privacy) were all the cameras wanted at the time. You know how paparazzi are; as soon as they get a whiff of a story (particularly a romantic one), they’re like a dog with a bone!
But from what we knew about Affleck, he wasn’t a big fan of the lights. Their very public relationship was all over the news for months and months, which led the public to question: are there wedding bells on the horizon?
So Affleck was coming off the back of his relationship with Paltrow before "Gigli" and JLo happened. The pair ran hot for each other from the very start. Apparently, Affleck wrote her letters (a lost art, boys and girls pay attention), and Lopez responded with songs!
And hey, you can’t forget Affleck’s racy cameo in her music video for ‘Jenny from the block’. It truly had the makings of romance for the 2000s. An engagement was definitely on the cards. But it seems that even a-listers get cold feet. In hindsight, JLo told the media it was the first time her heart had been properly broken.
Bye Bye Lopez
It was pretty heartbreaking for both of them to have to call it quits due to the fact the paparazzi couldn’t stay away from their relationship. The fact that Lopez and Affleck had gone so far as to plan a wedding (a role Jennifer Lopez was familiar with — remember "Wedding Planner"?) showed they were totally in love with each other.
C’est la vie, and adieu to Bennifer. The pair called off their engagement around early 2004. For Affleck, though, he was already jumping into another relationship soon after and ended up being married the following year. (Slow down, bud!)
On a first date, if the person you’re going out with has the same name as your ex, is that a problem for y’all? Not being too judgmental, but it would definitely irk some of us! Maybe Ben just always envisioned himself with a Jennifer.
After Lopez, Affleck married Jennifer Garner in 2005. He had known Jennifer previously, after co-starring with her in both "Pearl Harbor" and also in "Daredevil." Everything went pretty quickly — after his public breakup with Jennifer Lopez, Ben Affleck confirmed their whirlwind romance around late 2004.
But How Did It Start?
When the pair met, Garner was actually already married to fellow actor Scott Foley. This was back in 2000, mind you. It wasn’t until two years later that the pair met again and things got a little more serious.
At the time, Affleck was dating Jennifer Lopez (read on for the epic plot twist on this relationship years later), but he mentioned that it was the "Daredevil" set where the pair realized there was something more for them. So at the time, Affleck had feelings for Jennifer he couldn’t deny, but he was with his first Jennifer.
A Serious Love Triangle Again
The pair seemed to be crossing paths and making movies together, meeting once more when they starred on “Dinner for Five.” Even still, both Affleck and Garner were with the same partners as last time: Scott Foley and Jennifer Lopez.
Garner married, Affleck engaged — it definitely seemed that love was off the cards for them. But after the fated episode, Foley and Garner announced they were going to split up. And before you start, it wasn’t all about Ben!
Why Did Jen Divorce Scott?
So yes, there were some rather flirtatious looks between Garner and Affleck on that TV episode, but Foley vehemently denied any infidelity or “other person” as the reason for their split. He nobly acknowledged Garner’s rise to fame, the resultant success, and that sometimes people just... well, get divorced.
People, you should know the stats by now — it’s one in two couples (so 50%) whose marriage ends in divorce. A sad statistic but, it’s reality. So by May 2003, Garner had filed for divorce, and she was a single woman again!
Why Did JLo and Affleck Split?
Eight months later, MTV was quick to report that Hollywood’s A-List couple, Jennifer Lopez and Ben Affleck, had called it quits! In hindsight, Lopez reflected on their relationship that she felt “eviscerated.” Strong words. But clearly, she was very in love with Affleck!
Ben Affleck went into hiding and kept a low profile for a few months before making his first public appearance with none other than Jennifer Garner! The pair were watching the Red Sox (which makes sense seeing as Affleck grew up in Massachusetts), and following that, the paparazzi monitored their relationship and its progress.
The Romance Continues
Imagine: It’s October 2004, Bennifer was all over the news, and Affleck was madly in love with Garner. In April of 2005, Affleck romantically asked Garner to marry him. The two said “I do” in the ritzy Turks and Caicos in 2005. Ah, a dream beach wedding! Apparently, there were only four people at the ceremony, which was officiated by Garner's "Alias co-star Victor Garber.
A beach wedding is probably one of the most romantic. The only problem is maybe the sand, especially if it gets all up in your dress and your linen pants.
The pair’s relationship went from strength to strength, and together they had three children. Their first child, Violet, was born at the end of 2005 and enjoyed being the baby for four years until another one was on the way.
But more about Violet, who’s becoming the spitting image of her mother, Jennifer. No longer a baby, she’s been raised with some great values (and also raised to the same height as her mom!) because Garner always wanted her children to be grounded. It makes sense, seeing as Jennifer herself was raised in the south.
Bebe Number Two
We really dig the name Seraphina, which is of Hebrew origin and is derived from the highest-ranking angels of God! It’s also the name Garner and Affleck chose for their baby girl, who was born in early 2009.
It seems the time has definitely flown, as Seraphina becoming a fully-formed human. Despite the limelight, Garner and Affleck have ensured that their children understand that not everyone lives the glamorous LA lifestyle. Jennifer Garner sure seems like a great mom!
And Number Three!
Samuel Affleck was born in February of 2012. The youngest of Affleck and Garner’s kids, it’s been told to media outlets that he shares a close bond with his sisters, particularly middle child Seraphina.
And while Jennifer Garner seems like super-mom, that doesn’t mean Affleck gets off easy! He's been seen on “daddy duty,” taking young Samuel to extra-curricular activities.
Trouble in Paradise?
But even after over a decade and three beautiful children: even with all the lights and pros to being a celeb, their marriage just wasn’t working. Just after they had their 10th anniversary, Affleck and Garner filed for divorce, with it finalizing in October of 2018. Pretty sad.
In hindsight, Affleck has commented that it was a “regret” for him to divorce Jennifer. The pair did love one another and tried many times to make it work and give it a try. Sadly, however, it wasn’t enough.
What’s in Ben’s Closet?
The press was aflame with all sorts of terrible rumors of infidelity and such, but imagine the paparazzi’s delight when it turned out that infidelity was indeed the reason for their filing for divorce.
Apparently, by the time Ben Affleck’s extra-marital business came to light, he and Jennifer had already been separated for months. Sources said it was a nanny with whom he was involved — Christine Ouzounian — but there was also Ben Affleck’s battle with the bottle, which perhaps seems a more plausible reason for why the marriage didn’t work out, particularly with young kids.
Enter the Nanny
So you’re probably wondering what the other side of the story was, right? According to media articles and interviews, the quote that’s the juiciest is Ouzounian saying that, “he broke up with me… he told me he loved me, but he can’t be with me under these circumstances.”
Hmm.. what do you think? Other sources reported she acted as his confidante, particularly towards the end of his relationship with Garner. Anyway, Affleck was purportedly smitten over Ouzounian and insisted that she join him and his kids to the Bahamas after he and Garner split.
Jennifer’s Side of the Story
What immediately springs to mind when you think of a nanny in the middle of a celebrity marriage? Deception, right? While it sounds like Affleck and Garner had split a little while before Ouzounian was in the tabloids), Garner had her own thoughts on why their marriage ended, even after a decade.
It seems that while the spotlight makes things hard, for seasoned celebrities, they develop a thick skin — so the toughest part was actually going through the divorce. It seems that Garner is just like one of us, eh?
What’s It Like Being Under the Microscope?
In an interview with "Grazia" magazine, Garner reflected on how publically her divorce was followed. When she’d go to drop off her kids, the other celebrities in the neighborhood would be followed by just one paparazzo, whereas she had ten to fifteen following her.
She would hide before another A-lister’s nanny would make “the call” and alert media outlets that Garner was just trying to…you know, go to the park with her kids. Sounds pretty awful. But all in all, Garner still has some sort of relationship with her ex-husband, because after all, they do have kids together.
Life After Jen
Affleck kept a low profile for a time after his marriage ended — and we don’t blame him for it — like any other human, both Affleck and Garner needed time to recharge and reset, adjusting to new routines and people in their lives. The pair seem to be great co-parents to their kids.
Solid parenting, Bennifer. However, Affleck started getting a little lonely and moved on with a new woman within two years of his divorce. This time, Affleck was exploring if the old adage “blondes have more fun” was true and decided to…shake things up, we’ll say.
Shacking up With Shookus
Pardon us for the headline, but we can’t resist a good pun. Around July 2017, pics were snapped of a new Hollywood couple. "Us Weekly" found out that Affleck had been seeing the SNL producer, Lindsay Shookus, for a few years, albeit on and off.
At the time, the pair were both in relationships, with Shookus married to her former colleague, SNL producer Kevin Miller. Both Affleck and Shookus seemed to enjoy their relationship. However, his tendencies got in the way. Garner had to step in with an intervention in 2018 to ensure he was properly treated and supported.
Shookus Gives Affleck the Boot
A further public stint after a proud year sober seems to be what was the final straw for Shookus and Affleck’s romance. The pair had even moved into an NYC apartment, but it was not meant to be, with the pair ending their relationship around April 2018.
Affleck has proven in the past he was a fast worker, with a new woman in his arms just a few months later. He began dating Shauna Sexton, a former veterinary technician turned Playboy model. It was a short-lived romance, though, with rumors suggesting the pair only dated for a month or two.
Shookus Strikes Back
Following his dating stint with Sexton, Lindsay Shookus was back in the picture, but it seems that even after the years of on-and-off dating, it wasn’t enough to rekindle their flame. This time the pair were ending their relationship for good, putting an end to it around April 2019.
We’ve heard they’re still good friends. Amicable relations with exes seem like an impossible thing sometimes, but hey, they were both professional people working in the entertainment industry and were able to focus on their lives after their breakup.
Ben Affleck’s Bond Girl
Ana de Armas's involvement in the James Bond franchise is nothing new — and lucky Ben Affleck gets to say he dated a Bond girl! The pair met on the set of their film "Deep Water." A couple of little trips here and there, including a Cuban adventure where rumors started, were enough for the world to acknowledge the pair as a couple.
It was around May 2020 that their relationship was confirmed, and media outlets reported Affleck was “serious” about de Armas. However, by the beginning of 2021, the pair announced publicly that they had decided to split.
But Why Did They Break Up?
Before we move onto the very high-profile celebrity Affleck is currently dating, we just wanted to give a bit more background on Ana de Armas. Firstly, the pair had a 16-year age gap, which seems a lot, but Hollywood has actually seen much bigger differences throughout history.
But it seems that the pair just saw their lives going different ways. The events of 2020 also added pressure and made work commitments more pressing. Additionally, it was always important for Affleck to be close to his family, and ensuring he was close to his kids was paramount.
What’s Next for Ana?
The Cuban-born actress came onto the scene a few years ago. With her Spanish and Cuban roots (and looks), the beauty rose to fame and finally made it in America. More recently, you might’ve seen her in "Knives Out" alongside Hollywood hunk Chris Evans.
Move over, Ben Affleck, hello Captain America, you might say, but it seems that de Armas isn’t interested (nor is Evans for that matter). You’ll be able to see a few of Ana de Armas’ projects come to fruition very soon!
Can We Please Talk About This?
When we say “this,” we mean the Vulture article that claimed Affleck had kept a life-size cardboard cutout of Ana de Armas at his house.
A Twitter account broke the news first, saying that a cutout was seen being thrown into the trash one evening, along with a photo of said cutout being discarded by a man in a mask! Some speculate that it wasn’t Ben behind the mask but his brother Casey! Now we and the internet are wondering: did someone save Ana?!
Who Dumped Who?
Sometimes we hate being so high school about things, but some of y’all asked us who broke it off. Affleck and de Armas, who had apparently gone into quarantine together (big move: which ultimately made or broke up many couples), were fans of (sorry, advocates for) Dunkin’ Donuts.
Over the course of their relationship, the pair were repeatedly snapped with Dunkin’ iced coffees, and apparently, Affleck isn’t even affiliated with the brand; it’s just true love of the brand! But to answer your question, we needed to do a little more digging.
The Truth Shall Set You Free
After briefly becoming an influencer for Dunkin’ Donuts while romancing Ana, we got to the bottom of why the pair broke things off. What is touted as a quarantine romance, their summer fling came to an end when their different paths became, well, divergent.
Affleck was more LA, and de Armas had signed on to films that required her to be away. Also, the age difference: de Armas has aspirations to have children, where it seems that Ben doesn’t really want any more kids. Also, can we just point out that it’s difficult to introduce someone new to your ex-wife and the kiddies?
This Isn’t the First Time
It certainly isn’t the first time that Ben Affleck’s kids have come up as a reason to end a relationship. It was reported that this was the very same reason that Affleck’s relationship with Lindsay Shookus ended — because kids are always going to come first.
The difference this time was that Ben was indeed sober, something he’d battled with at the time he dated the SNL producer.
Jenny from the Block
Ben Affleck just can’t get enough of JLo, and wow, for someone who looks THAT good at her age (come on, look at the abs on her!), we don’t blame the guy. In the summer of 2021, Jennifer Lopez was captured celebrating on her yacht, but she was not alone!
The paparazzi had a field day — but only AFTER Jennifer made things Insta-official with a picture of her smooching Affleck. Numerous followers commented on the rekindled relationship before jumping to Affleck’s page, where his last post was an ode to his ex-wife, Jennifer Garner. Say what?
Garner Strikes Back?
Okay, we love the drama but also don’t need to start new rumors or anything. We’re just reporting things as we see them, and we couldn’t help but raise our eyebrows at the fact Ben Affleck had so obviously been celebrating his ex-wife.
The post, which features a montage of photos and videos of Jennifer Garner, also expresses his love for his ex. Seems kinda strange given the celebratory kissing pic from Lopez. The problem now is the fact that comparisons are being drawn between the two Jennifers. Maybe it’s the name; maybe it’s a fact they’re both high-profile celebrities.
Divorces Are Never Easy
It isn’t just Affleck who has had some marriage woes. In early 2021 Lopez split from major league baseball player Alex Rodriguez. The pair ended their 2-year engagement after realizing that they were better off being friends.
For Lopez, it would’ve been not her first, nor her second, or her third…but her fourth marriage. What we want to know is: did Jenny from the Block keep the ring? We know she definitely kept the gorgeous red Porsche. Fun fact: did you know that a young A-Rod appeared in JLo’s 1999 smash single ‘If You Had My Love’?
Some Backlash, Though!
So we are not totally against Jennifer Lopez being with Affleck, but let's calm down with the online comparisons between the two Jennifers. To be honest, we are older, wiser, and... we aren’t really still that petty, are we?
The nasty photos compare Garner working out to the glamorous photo shoots that Lopez regularly partakes in.
What’s the Story, Morning Glory?
The real news that y’all want to hear is: so how did Ben and Jen reconnect after all this time? So look, yes, we can confirm that the rumors of #bennifer being a thing again are TRUE! The canoodling resumed once again on a yacht in Malibu, and wow, we’re here for it.
The pair had an extremely public relationship in the early noughties, and now, it seems, they’ve found each other once again. The pair were snapped making out and hanging out together the whole weekend, apparently for Jennifer Lopez and her sisters’ birthdays.
Twenty Years in the Making
Just like that (well, almost 20 years later), the pair, who have both experienced a series of tumultuous relationships and public breakups, are back at it again.
It’s almost like their lives operated in a similar way — the same time that Affleck married Garner and stayed with her for almost 12 years, Lopez had married Marc Anthony and was with him for a decade herself! From LA to the Yellowstone Club, the pair have been snapped together various times.
Affleck Has Heart Eyes Only for JLo
The actor seems to have only good things to say, gushing about the singer and her dedication to her career and goals. Affleck gave "InStyle" magazine a juicy quote, saying, “I thought I had a good work ethic, but I was completely humbled and blown away by what she was committed to doing day in and day out.”
We kinda love the fact that Affleck is so into Jennifer. Who knows, maybe the pair will give love another try — maybe not wedding bells, but at least a new relationship to take them into the next phase of their lives.
What’s on the Cards?
For Lopez, it seems she’s going to continue to be a busy woman. She’s been set up nicely with Netflix to star and produce a sci-fi thriller, called "Atlas." She’s been working hard to secure a deal that spans a number of years.
Having Lopez on board means supporting diverse talent and ensure that women will be asked to step up as writers, filmmakers, and actors! Love love love! Between her films, new music (especially as she reconnects with her Latin roots and works with Latin musicians and producers), and TV series, Lopez is pent on keeping y’all entertained!
What About Ben?
Surely after years of drama (personal and relationship-wise), the actor can now settle into his niche and direct at peace?
We can say yes; that seems to be the case now. He has a beautiful woman on his arm (or at his chalet at least) and has a number of new projects in progress, which audiences can expect to see very soon!
Okay, But How Do the Exes Feel?
JLo and Affleck have mentioned that even their exes approve! Jennifer Lopez, who is co-parents with Marc Anthony, and Affleck, who does the same with Garner, both seem to have very supportive partners.
According to one source, “they all just want what’s best for each other and their families.” It all seems rosy, and all the reports are gushing about how ‘match made in heaven’ they are for one another, as well as how easily they fell back in love.
But How Do They Really Feel?
Sure, things sound good so far — both exes are happy if their exes are happy. But while Jennifer Lopez’s kids have met Affleck and seem to be okay with their mommy’s not-so-new boyfriend, apparently Garner has put the foot down.
When we say that, we mean that Garner wasn't too interested in having her kids meet Jennifer Lopez again as their father’s new girlfriend: not until things are more official. We can’t really blame her!
Aside from the public photos on Instagram, the paparazzi have been following the new romance very closely. A very cute date night at the Greek restaurant Avra Estiatorio in ritzy Beverly Hills saw the pair dine one-on-one in a private room!
After a few hours, they emerged, glowing like they were on their honeymoon! Jennifer seems just as smitten as Ben.
Happily Ever After
After finding their way back to one another, Ben and Jennifer Lopez seemed determined to make this time last. It took them a mere year of rekindled love to decide that they are taking things to the next level, and in April of 2022, they excitedly announced their engagement in a touching video on Lopez's website. JLo, who has seen her fair share of engagement rings, then became the proud wearer of a rare green diamond valued at $10 million.
This time, the couple followed through with the engagement! July of 2022 saw the two walk down the aisle in an intimate ceremony in Las Vegas. Tears of joy were shed all around. (Yes, by us too.)