Jennifer Lopez and Ben Affleck have been making headlines together again since 2021. More than 17 years after they called off their first engagement and ended one of the world’s most publicized romantic relationships of all time, rumors that they could be rekindling their romance turned out to be true.
Jen and Ben ended up engaged once again in 2022, less than a year after Ben was spotted discreetly visiting J.Lo’s home in Los Angeles, sparking the initial reconciliation rumors. Just a few months later in July 2022, J.Lo announced that she and Ben had taken off to Las Vegas and gotten married in a late-night ceremony. A month after that, they held a massive wedding reception in Georgia, and have been by each other’s sides ever since.
Ben and Jen said for years that they kept in touch with each other — mostly via email — after their breakup, and now we know that ultimately led to Bennifer 2.0. It’s been a lot of fun to watch them rekindle their romance over the past few years. They’ve been through a lot of ups and downs, and the public scrutiny has not ebbed much at all, but they seem a lot better at brushing it all off these days.
To be honest, we’re never quite convinced about getting back together with an ex, but Jennifer Lopez and Ben Affleck just have such awesome chemistry with each other, and their relationship makes us feel so nostalgic that we can’t help but root for them and their long-awaited marriage.
And when Jen’s documentary and accompanying album, The Greatest Love Story Never Told, in which she shares their journey from their perspectives dropped in February 2024, we were convinced these two are as solid as a rock. Still, just months later, divorce rumors started to swirl after years of critics claiming that Ben is miserable in their relationship. We don’t quite get that — we’re pretty sure he can leave whenever he wants and doesn’t have to stay in any relationship he’s unhappy in.
So in light of that, we’re doubling down on our support of Bennifer 2.0 and sharing their love story by taking a look back at some adorable throwback pics of Jennifer Lopez and Ben Affleck throughout their decades-long romance.
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Gym Casual
We all know hitting the gym is a major priority for J.Lo and it always has been. Ben is not quite the fitness junkie that she is, but they would still hit the gym together back in the day. These pics of them leaving a Beverly Hills gym early in their relationship are so early aughts!
Another One
Another day, another low-rise velour sweat suit and oversized get-up. Ben and Jen’s relationship is so definitive of the era it began in, it almost doesn’t even seem real. In this pic, they look like what we imagine costume designers would dress them in if someone were making a movie about their romance today.
That Glow
Jen’s signature glow totally rubbed off on Ben while they were together. He often sported a faux tan and gelled hair when he was with her, and he dressed up far more than we’ve seen him do since. J.Lo will not be seen on the shoulder of a schlub. Ben is handsome, no doubt, but she totally elevated his image.
'Gigli' Days
Jennifer was a big driving force in the “brown” trend of the early 2000s, especially while she and Ben were promoting their film Gigli. The two sometimes even coordinated their shades-of-brown ensembles. To be honest, the movie wasn’t great and neither was this particular fashion trend.
Jenny From the Block
This photo is emblematic of a moment in time. Ben looking like a Hollywood heartthrob and J.Lo, rocking her Juicy Couture sweat suit and giant gold hoop earrings could be a poster for the early 2000s. Seeing this pic takes us straight back to freshman year of high school and we kind of love it.
Better in Brown
Surprisingly, they did not coordinate their looks for the premiere of Gigli. Jen wore brown again, and it was a much better look than their casual attempt. Ben wore a black suit with a pale blue shirt and tie. They looked great, but for some reason, they didn’t seem quite as in sync with each other that night.
Unhappy Ben
Ben totally looked like something was upsetting him at the premiere of Gigli. It almost seems as if the couple got into an argument before the event. That’s just speculation of course, but it’s a far cry from many of the other pictures we’ve seen of Ben and Jen from earlier in their relationship. Jen always has her game face on, so it makes Ben’s discomfort even more obvious.
Stop the Madness
Ben and Jen presented a completely united front on this sunny day in Los Angeles, but they were undoubtedly being hounded by the paparazzi and they don’t look thrilled about it. Both have said that being overwhelmed by the media contributed to their breakup, and it’s totally understandable.
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Happier Here
Ben and Jennifer have always known how to make each other smile, though. They were obviously very into each other throughout their relationship. Jen even said in her 2014 memoir, True Love, that she thinks her split with Ben was her first real heartbreak. It’s no surprise they’ve seemingly reconnected.
Love & Sports
Jennifer enjoys sporting events and she’s been spotted attending them with a lot of her exes, including Alex Rodriguez and Marc Anthony. Jen and Ben went to baseball games together all the time. He’s a huge Boston Red Sox fan. Some have even said that when she performed at the Global Citizen Vax Live concert in 2021, she performed “Sweet Caroline” as a nod to Ben, since it’s somewhat of an anthem at Red Sox games. He also attended the Vax Live event, so he would have noticed.
Bonding Moments
They really did seem to bond over their love of sports. Ben and Jen were seen cheering, celebrating, and even teasing each other at sporting events on various occasions. They didn’t always root for the same team, but they always looked like they were having a blast with each other, regardless of who was winning.
Sweet Nothings
They were also caught whispering into each other’s ears on multiple occasions, but by the look of Jen’s smile here, maybe Ben’s whispering more of a sweet something than a sweet nothing. There’s a bit of mischief in his eyes, too. They had such a connection throughout most of their time together.
Hand-in-Hand
We loved seeing J.Lo and Ben hand-in-hand back in the day. It always felt like a sign like they were still going strong. We didn’t know anyone who wanted to see them split up — at least not before we got to see what we knew would be some epic wedding pictures. It was not to be, though. At least not then…
Jetsetters
They were jetsetters then, and they’re jetsetters now. Jennifer and Ben reportedly took her private jet to Montana in May 2021, fueling rumors of a rekindled romance. Photos of them disembarking the jet when they arrived back in Los Angeles surfaced the next day. It felt like going back in time.
Lunch Date
Jen is a notorious tee-totaler, but she was a bit more relaxed during her relationship with Ben. Here they were spotted out for lunch and each with a glass of Champagne. Ben has struggled with alcoholism and been in and out of rehab since they split up though, so any future dates likely won’t include imbibing.
So Gorgeous
It’s almost unfair what a beautiful couple Jennifer Lopez and Ben Affleck made. They looked absolutely gorgeous together, whether they were dressed to the nines or in gym clothes. Just imagine what Jen’s stylists could do for Ben now! We would love seeing them together on the red carpet again one day.
Bad Habits
Ben had some bad habits, even when he was engaged to Jennifer. She never seemed to hold it against him though, at least not publicly. She seems really good at not letting anyone influence her commitment to herself and her own success and we totally admire that about her. “She remains, to this day, the hardest-working person I’ve come across in this business,” Ben said about her in the May 2021 issue of InStyle magazine.
Plenty of PDA
Jen and Ben were never shy about the PDA, which is probably one more reason the paparazzi loved them so much. It made for great photos, but for fans it was also one way we could live vicariously through them. They seemed to share a lot of passion and just couldn’t resist expressing it no matter where they were.
Always Professional
But they made a ton of public appearances together while promoting their various projects and they were quite professional. The reality is, as Hollywood stars, a part of their job is showing up and creating a fantasy moment for their fans. Their relationship definitely enhanced that for both of them.
Nightlife Vibes
Jen is rarely photographed out on the town these days, and looking at pictures of her and Ben remind us that there was a time before she had kids and an entire empire to run, that she would let loose and spend a night partying (in the most innocent way) with her man. They were so glamorous together!
And Again … So, So Pretty
We couldn’t help but include just one more shot of Ben and Jennifer looking so, so pretty. They really were just the best-looking couple. Go ahead, soak it all in and cross your fingers that even if it doesn’t last, we’ll get some more totally glam moments from Bennifer one day in the near future.
