Leading Ladies & Pop Stars: Ben Affleck’s Dating History

Most actors in Hollywood get a reputation for having laundry lists of lovers once they reach celebrity status. Ben Affleck certainly got that reputation, but when we dove into his romantic history, we found that compared to some of his peers, Affleck has a shortlist of exes.

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There’s no correct amount of relationships to have in Hollywood, and Affleck has chosen a more selective approach. He has dated some of the most accomplished and beautiful women in the industry, married one, and is still looking for his partner-in-crime. Take a look back at Ben Affleck’s former flames.

Who Is Ben Affleck?

Best to begin with some background on this Hollywood actor! First of all, let’s discuss this man’s salary because it’s a big one! Ben Affleck is a very well-paid actor and has a current net worth of nearly $150 million. Yes, you read that number correctly, and it’s way more than what we have in the bank!

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The actor, director, producer, and screenwriter has been in show business for over three decades! You probably recognize him from “Good Will Hunting” (which he wrote and appeared in with his longtime friend Matt Damon), “Armageddon,” “Gone Girl,” “Argo,” and playing Batman.

All You Need Is Love

Alright, fine, we will get to the real reason for the article, Ben Affleck’s love life. Let’s explore the Ben Affleck timeline of romance and the famous women he’s been with over the years. You are most likely to recognize two of them, but the other women may surprise you.

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Alongside the other celebrities he’s dated, Ben Affleck’s love life started off in a pretty common way with his high school sweetheart. For this list, we’re going all the way back to high school to meet the first person who stole Affleck’s heart. But is this person?!

Together Since Age Eight

Ben Affleck was born in California but grew up right outside of downtown Boston, in Cambridge. His parents were deeply involved in the arts, and it was his mother who actually encouraged him to explore acting. When he was eight years old, he met Matt Damon, and the two became lifelong close friends.

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Surprise! This bromance has been going strong for more than 40 years, both of their longest relationships. The pair have gone on to co-star in many movies, in addition, to write and direct together. We know they’ll continue to collaborate!

A Bromance for the Ages

We like to imagine that these two simply made eye contact and had an instant connection. But in reality, their mothers were instrumental in setting up their friendship. Affleck and Damon lived a couple of blocks away from each other and also attended the same high school.

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Damon once revealed in an interview that Affleck fought off a bigger student that was picking on Damon. After tackling the bully, Damon knew that he had himself a good friend. And through the ups and downs, the pair have continued their friendship today.

The First Romantic Relationship

Let’s refocus on Affleck’s romantic ventures. Let’s talk a little about Affleck’s high school years and his first serious girlfriend, Cheyenne Rothman. The two met as teenage high school students and first got together in 1990. They dated for seven years before parting ways.

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The breakup was most likely due to Affleck’s overnight fame after “Good Will Hunting.” Whether it was different values or personal growth, we’ll never be sure, but seven years is impressive for people so young! Rothman became a short-film director and set the stage for Affleck’s future partners.

Affleck’s in Love

Affleck’s in Love? It doesn’t quite roll off the tongue the way that Shakespeare in Love does. Even when Gwyneth Paltrow is the one calling out from across the stage. You guessed correctly! Gwyneth Paltrow was the first fellow actor with whom Ben Affleck dated.

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It’s speculated that Affleck broke up with Rothman and rebounded by dating Paltrow. Sounds like a quick turnaround. The two dated for nearly three years, during which they appeared in two films together. One was the award-winning film, “Shakespeare In Love,” and the other was 2000’s “Bounce.”

Bounce… To the Next Lady?

Shortly after his split from longtime girlfriend, Cheyenne Rothman, Affleck into a relationship with Gwyneth Paltrow from 1997 to 2000. Technically, they dated on and off during that time. They got together after Affleck first met Paltrow at a dinner party.

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While making “Bounce” in 2000, Paltrow and Affleck reunited. However, this didn’t last very long, and by the end of that year, the couple had gone their separate ways. They seemed to make a nice celebrity couple, but some relationships aren’t meant to last forever. Luckily for Ben, he was able to move on.

Checking Himself Into Rehab

After the split, Ben Affleck voluntarily entered into a residential 30-day rehab program for alcohol abuse. It is unclear if it was because of his relationship ending or the wild Hollywood party culture, or a combination of many things. Regardless of the reason, fans were happy to see Affleck taking care of himself.

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This treatment stint would hold Affleck for quite a number of years but wasn’t his last time in rehab. This was a battle that he would continue to try and overcome throughout his entire career. Affleck had no clue that soon after finishing his program, he’d be engaged!

(J)Lo and Behold, His Next Girlfriend

Enter Jennifer Lopez, Jenny from the block, JLo; whatever you’d like to call her. Whether it was Affleck’s charm that gripped JLo or her beauty that drew him to her remains a mystery. What we do know is that the couple took Hollywood by storm, and fans were living for it.

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Tabloids called them “Bennifer” after they worked together on the movie “Gigli.” The pair dated for two years after JLo’s divorce from Cris Judd was finalized in 2002. Affleck and JLo were not shy about showing their affection for each other, and it wasn’t long before things became serious.

Becoming the Paparazzi’s Favorite Couple

This highly followed pair (seriously though, we don’t believe that they got a moment of privacy) were all the gossip magazines wanted at the time. You know how tabloids are; the moment they get a whiff of a story (especially a romantic one), they’re like a moth to a light!

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But Affleck was pretty clear that he wasn’t a large paparazzi fan. Their very public relationship was covered by magazines for countless months. This led to many fans and media outlets wondering if these two lovebirds would be walking down the aisle anytime soon.

Celebrity Couple of the 2000s

The couple was hot for each other from the very beginning. According to a couple of sources, Affleck wrote her notes, and JLo responded with personalized songs! And nobody could possibly forget Affleck’s frisky cameo in her “Jenny from the Block” music video.

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It was truly building itself into the epitome of celebrity romance in the 2000s. Everything seemed to be leading up to an engagement. But even A-list celebrities can be nervous and get cold feet. Looking back on it, JLo that it was her first time dealing with heartbreak.

From Wedding Plans to Heartbreak

It was really sad for both of them to have to split up because the paparazzi wouldn’t leave them alone for a second. The fact that JLo and Affleck had even discussed and started to plan a wedding (similar to JLo’s movie, “Wedding Planner”) was further proof that they were completely in love with one another.

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And that was the end of Bennifer. The couple called off their engagement in early 2004. For Affleck, though, he quickly jumped into another relationship and ended up married the year after his split from JLo.

Dating a Second Jennifer

On a first date, if the person you’re meeting has the same name as your ex, is that an issue for y’all? Not trying to pass judgment, but it would definitely be a problem for some of us! Perhaps Affleck just always had a thing for women with the name Jennifer.

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In 2005, Affleck and Jennifer Garner got married. He had initially gotten to know Garner through professional projects like the movies “Pearl Harbor” and “Daredevil.” After Affleck’s highly publicized split from Jennifer Lopez in early 2004, he confirmed that he had moved onto Jennifer Garner later that year.

How Did We Get Here?

When the two first met in 2000, Garner was actually already married to actor Scott Foley. They would have to wait another two years until the couple met again, and things started taking a bit of a more serious turn.

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During that time, Affleck was in a relationship with Jennifer Lopez, but he said that it was on the “Daredevil” set where he and Garner realized there might be something more there. So, in summary, Affleck had romantic feelings for Jennifer but was dating the other Jennifer. Got it? Yeah, we’re confused too.

Paths That Continued to Cross

Affleck and Garner seemed to be running into each other more and more. Soon enough, they were getting hired to star in more films together, like when they appeared on “Dinner for Five.” Despite these signs from the universe, Affleck and Garner were still with the same partners as last time: Foley and JLo.

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With Affleck engaged and Garner married, it certainly appeared that love was not in the cards for them. But after starring in that episode, Garner announced that she and Foley were splitting up. And the most surprising part was that it wasn’t because of Affleck!

Single Jen Once Again

So while there may have been some rather flirtatious glances between Affleck and Garner on that TV episode, Foley fiercely denied any cheating or “other person” as the reason behind their split. He openly acknowledged Garner’s rise to fame, the success that resulted from the newfound fame, and that sometimes marriages just don’t work out.

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The statistics are pretty well-known at this point — about 50% of all marriages end in divorce. An unfortunate statistic but, it’s the world we’re living in. By early 2004, Garner’s divorce had been finalized, and she was single!

The End of the Bennifer Era

Around that same time, MTV was quick to share that Ben Affleck and Jennifer Lopez were also newly single! After some reflection on her relationship with Affleck, Lopez said she felt completely gutted. Those are some choice words. But obviously, she loved Affleck very much!

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Ben Affleck kept a low profile for several months before returning to the public eye with none other than Jennifer Garner! The pair were attending the Red Sox (since Affleck is a huge Boston sports fan), and after that, the paparazzi followed their relationship as it progressed.

Dreamy & Intimate Beach Wedding

Picture this: It’s October 2004, Bennifer was in every magazine, and Affleck was head over heels for Garner. In April of 2005, Affleck bucked up the courage to ask Garner to be his wife. The two exchanged vows in Turks and Caicos that same year.

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Everyone’s dream beach wedding! Supposedly, there were only four people who attended the ceremony, which was officiated by Victor Garber, Garner’s “Alias” co-star. We wonder who the other three attendees were! With the beach setting and intimate guest list, the ceremony was likely filled with love and romance.

Welcoming Their First Child

The couple’s relationship continued to grow and strengthen, and together they welcomed three kids. Their first child, Violet, was born at the end of 2005, and not too long after, her parents said, “I do!” Garner and Affleck basked in being new parents to their daughter for a few years before having more children.

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These days, Violet has grown into her mother’s clone. She has been raised with solid values and as out of the spotlight as possible since Garner always wanted her kids to be grounded. It’s all pretty similar to Garner’s own experience growing up.

Family of Three Becomes Four

After a number of years with only Violet in the house, Garner and Affleck figured that it was time to add another baby to their family. Fast forward to early 2009, and the pair did just that. The family of 3 became a family of 4 with the addition of their second daughter, Seraphina.

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The time has just flown by as Seraphina entered her teenage years. Even though they’re famous, Garner and Affleck have made sure that their kids understand that not everyone lives such glamorous lifestyles. Jennifer Garner seems like a really dedicated mom!

A Son Joins the Family

Affleck was happily outnumbered by the number of women he lived with. His and Garner’s family seemed to be doing well, and the sisters were growing up nicely together. In February 2012, the male energy in the family was evened out a bit with the arrival of Samuel Affleck.

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Magazines have reported that Samuel is close to both of his siblings, especially Seraphina. And while Jennifer Garner appears to be juggling her mom and working hats effortlessly, that doesn’t mean Affleck isn’t doing anything! There have been sightings of Affleck bringing his son to afterschool activities.

Unable to Make It Work

But even after ten years of marriage, three vibrant children, and all the bells and whistles that came with being a celebrity, their marriage just wasn’t working anymore. Shortly after they celebrated their 10th anniversary, Affleck and Garner announced their separation.

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The divorce was finalized in late 2018. In years since the divorce, Affleck has expressed how much regret he feels for divorcing Garner. The two did genuinely love each other and tried countless times to make it work out. Sadly, though, love by itself just wasn’t enough to move past their issues.

Rumors and Stories Circulating

As with any A-list celebrity couple split, the press was buzzing with all kinds of awful rumors of cheating and other women being involved. One such rumor that just didn’t seem to go away, to the press’ delight, was one that included Affleck, their nanny Christine Ouzounian, and a poker game in Vegas.

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Affleck’s team adamantly denied these rumors and even threatened to sue the media outlets that perpetuated these claims. There was also Ben Affleck’s alcoholism, which seems like a more realistic reason for why the marriage ended, especially with young children.

The Nanny Speaks Up

So, you’re probably dying to know what this nanny said, right? According to interviews with a few magazines, Ouzounian basically said that Affleck broke up with her. She said that he told her that he loved her but that their situation wasn’t going to work out.

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Garner said that she and Affleck had been separated for months before the nanny rumors even surfaced. Towards the end of his marriage with Garner, apparently, Affleck leaned on the nanny. Anyway, Affleck had Ouzounian join him and his children on vacation after he and Garner split.

Divorce is Tough, Even for Celebs

When you hear that a nanny might have something to do with a celebrity divorce, where does your mind go? Cheating scandal, right? While it sounds like Affleck and Garner had split before Ouzounian was brought into the divorce narrative, Garner had her own thoughts on why their relationship didn’t work out.

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It appears that even after ten years, the pressure of the spotlight and Affleck’s battle with alcohol addiction were the actual leading causes. Garner said that the toughest part of going through this divorce was actually going through the divorce process, regardless of the paparazzi’s presence.

Having Paparazzi Follow Your Every Movement

Garner reflected on just how public her divorce was in an interview with “Grazia” magazine. When she’d drop her kids at school, the other celebrities in the neighborhood would maybe be followed by one paparazzo. Comparatively, she would have ten to fifteen tailing her.

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When she would take her children to the park, Garner would see nannies in the neighborhood call the media outlets to let them know where she was. Sounds like a nightmare. But, after the initial shock wore off, Garner and Affleck built a co-parenting relationship for the benefit of their children.

Moving On and Moving Forward

Affleck avoided the spotlight after his divorce was finalized — and we don’t blame him — like any other human, both Affleck and Garner wanted time to recenter and reset, adjusting to their new normal with new routines and boundaries. The couple appears to be making co-parenting work for their family.

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Nicely done, Bennifer. But Affleck started feeling a bit lonely and started dating a new woman within two years of his divorce. For the past decade and a half, he had only been with women who were in front of the camera. This time, Affleck took a different approach.

Behind-the-Scenes With Shookus

Starting in July 2017, photos were taken of a new Hollywood couple. “Us Weekly” found out that Affleck had been going out with one of the producers on Saturday Night Live, Lindsay Shookus. The pair had seen each other on and off for a couple of years.

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At the time, the pair were both after divorces, with Shookus separated from her former colleague, SNL producer Kevin Miller. Both Affleck and Shookus took it slow. Shookus wasn’t used to the attention that came with publicly dating a celebrity. Perhaps that was more than she could handle and led to their breakup.

From Shookus to Sexton

The couple had been having dates between New York and California when Affleck was photographed grabbing dinner with Shauna Sexton, a Playboy model. A few days later, Shookus and Affleck confirmed that after about a year together, they were calling it quits in August 2018.

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Affleck has shown in the past that he tends to bounce back fairly quickly with a new woman after a split. He started casually seeing Sexton; the former veterinary technician turned Playboy model that he got dinner with. It only lasted about a month or two before it ended.

A Brief Shookus Encore

After his brief fling with Sexton, Lindsay Shookus came back into the picture. She was impressed with Affleck’s dedication to his sobriety and recent rehab stint. However, that admiration wasn’t enough to keep the relationship going. The couple ended it for good in April 2019.

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According to a number of sources, they’re still good friends. Friendly relations with exes seem like an impossible goal sometimes, but they were both professional industry people who ended things for real, logistic reasons – it’s tough building a relationship when kids live on opposite coasts.

Short-lived Bond With a Bond Girl

Ana de Armas was involved in the James Bond franchise, and Ben Affleck is lucky enough to say he dated an actual Bond girl! The couple met on the set of their movie “Deep Water.” A handful of trips here and there, including to Cuba, where rumors originated, added up to global acknowledgment that the two were a couple.

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It was during May of 2020 that their relationship was confirmed, and tabloids reported Affleck was “serious” about his relationship with de Armas. However, by the start of 2021, the couple announced that they had decided to part ways.

Going in Different Directions

Before we continue onto the very high-profile celeb that Affleck is currently linked to, we just wanted to provide a little more background about Ana de Armas. For starters, the pair had 16 years between them, which seems substantial, but Hollywood has seen its fair share of larger differences throughout history.

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But it looks like the couple just saw their lives going in different directions. 2020 also added pressure and made work commitments more stressful. Plus, it was always critical for Affleck to be near his family, and making sure that he was close to his children was paramount.

Up Next for Ana

The Cuban-born actress broke into showbiz a few years ago. With her Cuban and Spanish roots (and looks), the beauty broke into the spotlight and finally made it in America. Most recently, you may have seen her in “Knives Out” with co-star Hollywood hunk Chris Evans.

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Goodbye, Ben Affleck, and hello, Captain America! Wouldn’t that be something? But it looks like de Armas isn’t looking for anything or interested (nor is Evans as far as we can tell). You’ll be able to catch a few of Ana de Armas’ projects come to theaters really soon!

Someone’s Got to Address This

When we say “this,” we are 1000% referring to the recent Vulture article that claimed that Affleck used to have a life-size cardboard cutout at his house. And it wasn’t of himself as Batman. The reported subject of said cutout was none other than Affleck’s ex-girlfriend, Ana de Armas.

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A Twitter account first shared the story with a picture and caption describing a masked man discarding a cardboard cutout. Some think that it wasn’t Affleck wearing the mask but his brother Casey! Now the biggest question everyone on the internet has: did anyone rescue the Ana cutout?!

The Nitty Gritty Details

Oftentimes we don’t enjoy being so high school about things, but questions have arisen about who broke up with who. Affleck and de Armas had supposedly gone into quarantine together (a huge move: which ultimately strengthened or broke up numerous relationships), were super fans of Dunkin’ Donuts.

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While they were together, the couple were constantly seen and photographed with Dunkin’ iced coffees, and apparently, Affleck isn’t even paid by the brand; he just genuinely loves the brand that much! But to answer the more pressing question, it required a bit more investigating on our part.

End of a Quarantine Romance

After briefly becoming a Dunkin’ Donuts advocate while dating Ana, we got to the bottom of why the couple split up. What is called a quarantine romance, their summer fling ended when their different paths conflicted with each other.

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Affleck lived in LA, and de Armas had movies that required her to travel. Additionally, the age difference: de Armas has dreams of being a mom, where Ben seems content with his three children. Also, can we just highlight how difficult it is to introduce someone new to your ex-wife and children?

Children Always Take Priority

It definitely isn’t the first time that Ben Affleck’s children have come up as a reason to break up with a girlfriend. It was speculated that this was one of the actual reasons that Affleck’s relationship with Lindsay Shookus ended — because their children are always going to come as first priority.

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The biggest difference this time was that Affleck was fully sober and committed to staying that way, which was something that he struggled with while he was dating the SNL producer. If there’s anything de Arma took away from this, we hope it’s admiration for Affleck’s dedication to parenting.

We Love a Full Circle Celebrity Couple

Ben Affleck had a thing for JLo, and for someone who looks THAT incredible at her age (just check her out!), we can’t argue with the man for still being into her. During the summer of 2021, Jennifer Lopez was photographed celebrating on her yacht, but she was hardly celebrating alone!

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The tabloids had a field day — but only AFTER JLo made things publicly official on Instagram with a photo of her kissing Affleck. Countless followers commented on the rekindled couple before checking Affleck’s account, where his most recent post was an ode to his ex-wife, Jennifer Garner…

Oddly Timed Appreciative Post

Normally celebrities feuding is really fun to follow, but this observation seems a bit less dramatic than that. We’re just sharing things as we see them, and we couldn’t help but find it interesting that Affleck so publicly celebrated his ex-wife shortly before kissing his old-new girlfriend.

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The post featured several pictures and videos of Jennifer Garner and expressed his love for her. If anything, the timing seems odd given the celebratory kissing photo from JLo. The issue now is the fact that the two Jennifers are being compared. Perhaps it’s the name; maybe it’s their celebrity statuses.

Divorces Are Always Tough

Affleck isn’t the only one with an unsuccessful marriage in his past. In early 2021 JLo broke up with former Major League baseball player Alex Rodriguez. The couple ended their 2-year engagement after concluding that they were better off as friends.

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For JLo, it would’ve been her fourth marriage. What we’re left wondering is if she kept any of her wedding gowns or rings? We know she kept the beautiful red Porsche. Fun fact: did you know that a young A-Rod cameoed in the music video for JLo’s 1999 smash single ‘If You Had My Love’?

Gross Online Comparisons

Too often, tabloids and media outlets love to pit women against each other, especially if there’s a shared romantic past with the same partner. We’re not sure how we feel about this JLo and Affleck reunion after all of these years, but the online comparisons between JLo and Garner need to stop.

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It only makes it worse that they’re both named Jennifer. To be honest, we are wiser, more mature, and… we aren’t still that petty, are we? The rude comparisons often include pictures of Garner working out alongside glamorous photoshoots that JLo participated in.

Reconnecting and Reconciliation

The most important question we want answered is: how did Affleck and JLo reconnect after all of these years? So, here’s the thing, we can confirm that the whispers of #bennifer being a thing again are accurate! The cuddling resumed again on another yacht in Malibu, and they both seemed happy.

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The couple had an extremely public relationship in the early ’90s, and now, it looks like they’ve found their way back to each other. The pair were photographed kissing and hanging out together the entire weekend, apparently for JLo and her sisters’ birthdays.

Officially Back Together Again

Almost two decades after the fact, the couple, who have each experienced their fair share of hectic relationships and public splits, are officially back together again. This happens so infrequently for celebrity couples that we’re honestly pretty shocked.

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It’s almost as if their lives operated in similarly parallel ways — during the same time that Affleck married Garner and was with her for nearly 12 years, Lopez had married Marc Anthony, and they were together for a decade! From LA to the Yellowstone Club, the couple has been photographed together numerous times.

Entering the Next Phase Coupled Up

The actor has only had good things to say, talking about the performer and her dedication to her goals and career. Affleck spoke with “InStyle” magazine and admitted that he thought he had a pretty respectable work ethic, but he was humbled and inspired after seeing JLo every day.

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We love a man like Affleck, who is so comfortable complimenting the women in his life for their strengths. Who knows, perhaps the couple will give love another try — let’s not jump to the altar just yet, but at least a new relationship to enter into the next phase of their lives with.

Project After Project After Project

For JLo, it looks like she’s going to keep on being a busy woman. She’s set herself wonderfully with Netflix and is set to star and produce a sci-fi thriller entitled “Atlas.” She’s been putting in the work to secure a deal that continues for several years.

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Having JLo partnering with Netflix means supporting diverse talent and put women in positions to write, direct, and lead casts! We love this boss move! Between her movies, new music, and TV shows, JLo is dedicated to keeping y’all on your toes and entertained!

What Does This Mean for Ben?

JLo is keeping herself quite preoccupied, but what does that mean for her new leading man, Ben Affleck? Surely after years of relationship and personal drama, the actor can finally get some peace and settle into his love of directing projects?

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Based on what we see currently, the tentative answer seems to be yes. He is officially dating a beautiful woman who understands what it means to be dating while prioritizing children and has many new projects in the works, which audiences can expect to hear more about very soon!

What Say You, Jennifer Garner and Marc Anthony?!

JLo and Affleck have explained that both of their exes approve of their relationship! JLo, who is co-parents with Marc Anthony, and Affleck, who has the same arrangement with Jennifer Garner, both appear to have very supportive and open-minded partners.

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One source has said that everyone involved just wants what’s best for one another and their children. It almost seems too good to be true, and all the magazines are reporting about how great of a pair they are, in addition to how naturally they fell back in love with each other.

Taking a Cautious Approach

Yes, things sound great so far — every person seems to be happy that everyone else is also happy. But while JLo’s children have spent time with Affleck and seem to be fine with their mother’s not-so-new boyfriend, apparently Garner has taken a different approach.

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By that, we mean that Garner seems a bit more cautious about this whole thing. With her kids involved, she wants to be intentional with timing when they were going to meet JLo as their dad’s new girlfriend. She wanted to make sure that things were serious and official before her children became involved.

Enjoying the Time Together

The main source of this relationship has been from publicly posted pictures on Instagram. Seems like the couple is trying to control their own narrative this time around. But don’t worry, the paparazzi are still very much following this rekindled relationship and have managed to snap some photos of their own.

Source: Backgrid

Like this adorable date night! Paparazzi captured Affleck and JLo cozying up at Avra Estiatorio, a Greek restaurant in Beverly Hills. According to sources, the couple had reserved a private section for a more seclusive date night experience. As they were leaving the restaurant, JLo and Affleck seemed smitten.

Wishing Them the Best

For better or for worse, Ben Affleck has lived much of his life under the microscope. Affleck had his own obstacles to overcome in addition to dodging the court of public opinion. Hence, his relationships are also scrutinized. But these days, he seems to be in a really good place.

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He has faced his issues head-on, put an emphasis on his family, found a passion for directing, and now has someone to celebrate these things along with his upcoming projects. For now, Affleck seems to have found a supportive partner in JLo, and we wish them the best!