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Ben Affleck gifted JLo a 4-minute video montage for Valentine’s Day and yes, it’s mandatory viewing


By Sarah Finnan
15th Feb 2022
Ben Affleck gifted JLo a 4-minute video montage for Valentine’s Day and yes, it’s mandatory viewing

Some get flowers or chocolates or jewellery for Valentine’s Day… JLo gets four-minute video montages.

Ben Affleck and Jennifer Lopez rekindled their romance last summer and it’s been a steady stream of pap pics, PDA and “power couple!” headlines ever since. People long had their suspicions that a noughties resurgence was on the way, but Bennifer’s recoupling all but confirmed it. They were the it-duo of the early aughts, after all.

Thrilled as we were (and still are!) that young love’s dream found their way back to each other – after over 17 years apart – Ben Affleck’s flirting techniques still never fail to surprise us. They need work, there I said it. Yes, I know that they’ve (somehow) worked on JLo thus far, but to the outside observer, his methods are a little… unusual, shall we say. 

Take his Valentine’s Day gift to Jen, for example. Forgoing the traditional flowers or chocolates in favour of something more personal, Ben went heavy on the nostalgia this year and gifted JLo a four-minute-long video montage of their best moments. No, I’m not joking. 

Borrowing footage from a mishmash of different sources, the finished product is as much an ode to the early 2000s as it is their relationship and includes clips from such cultural touch points as the “Jenny From The Block” music video, Gigli – the film that originally introduced them to each other, and even a few outtakes of Affleck and his other love, Matt Damon, back when they filmed filming Good Will Hunting together in the late 90s. 

Clearly putting his extensive filmmaking experience to good use, the tribute video is set to her new song “On My Way” (from the recent rom-com Marry Me in which she stars alongside Owen Wilson) and even has some kitschy edits and suave transitions added in for extra enjoyment. 

How did we manage to get our hands on the special gift? Seems JLo was apparently so impressed that she decided to share it with, well, everyone. “I am going to share something very special and personal with you that normally I would only share with my inner circle,” she wrote in her most recent newsletter.

“It’s an early Valentine’s Day present from Ben. Watching it made me think about the journey of true love, its unexpected twists and turns, and that when it’s real, it actually can last forever,” she continued, before adding, “This seriously melted my heart.”

This isn’t the first time that Ben has made such a grand gesture though. In fact, it seems he hasn’t updated his schmoozing skills since he first set his sights on JLo back in 2002 and took out a series of half-page ads to tell the world how much he loved working with his then-colleague. 

At the time, Ben said the move was to counter emerging comments that Jennifer Lopez was a diva, but seriously, who spends $15,000 to fix someone’s reputation unless they have their eyes on a different prize?  A few weeks later, Bennifer was born.

Then last summer, his questionable (albeit effective?) flirting techniques struck again when he began wooing Jen after an almost two-decade-long breakup. According to TMZ, the newly re-minted pairing hadn’t come as out-of-the-blue as fans might have thought and Ben had seemingly been courting his former fiancé (and then-fiancé to Alex Rodriguez) via email. Yes, email, the sexiest of all communications. Guess, we really are back in 2002.

Not the rebound fling we all presumed their reunion to be, Ben had apparently been laying the groundwork for months already, with the first correspondence sent as far back as February (their relationship was subsequently “confirmed” in May). 

JLo was in the Dominican Republic to film the movie Shotgun Wedding at the time and TMZ reports that Affleck supposedly saw photos of his ex, and recently single himself, decided to email her to tell her “how beautiful she looked and how much he wished he could be down there with her”.

An onslaught of mushy-gushy emails ensued, one particular one proclaiming Affleck’s unwavering confidence that he could “own” JLo’s heart “with his pen”. If that makes you uncomfortable, you’re not alone… he’d probably give Ross Gellar a run for his money with those techniques. 

Maybe it’s just wherever JLo is concerned that his flirting falls short? Not so, at least according to this TikTok which details another of Affleck’s dodgy attempts to find love. Uploaded by model Nivine Jay, the viral video recounts how the actor once sent her a private video message on Instagram after she unmatched him on the dating app Raya (because she thought it was a fake account). 

@nivinejay

Sorry Ben ?? #raya #benaffleck #dating #fyp

? original sound – Amir Yass

Later resharing the clip on TikTok, Affleck can be heard asking her, “Nivine, why did you unmatch me? It’s me.” I’ll let you make your own judgements here, but the second-hand embarrassment is too much for me. 

Putting yourself on film for a potential paramour is never a good idea, even if it’s to prove you really are Ben Affleck. I guess famous people are just as hopeless and awkward and desperate for love as the rest of us are.