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Image / Agenda / Breaking Stories

We need to talk about Ben Affleck’s flirting techniques


by Sarah Finnan
12th May 2021

Jimmy Kimmel / Instagram

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Supposedly Ben Affleck has been wooing JLo for months via email, which reminded us of how he wooed her way back in 2002 through the equally sultry medium of print advertising.

Interesting us all the more these days, it’s hard to nail down exactly why we’re all so taken with the courtship, but perhaps it’s down to the fact that we have little other personal drama to keep us going. Our WhatsApp groups have essentially run dry of our own news, and so we’ve turned to the Hollywood elite for entertainment instead. 

JLo is the gold standard of celebs and while we’ve always had a bit of a soft spot for Ben Affleck, he’s oddly shot to top of the hotlist since being reassociated with his former “Jenny from the Block” flame. An opinion Sharon Stone seems to agree with judging by a comment she left under a recent Instagram post… 

From that meme of him dropping his tray of Dunkin Donuts coffees, to the paparazzi snap of him smoking a cigarette outside his front door,  it’s clear that Ben Affleck is the king of relatable content. But… we need to talk about his flirting techniques, because we reckon they need some work – at least from the outside looking in they do. 

No doubt you’ve already heard all about his online dating exploits by now, but if not let me fill you in. Basically, Affleck hit the headlines mere days ago after a video by model Nivine Jay went viral on TikTok. Detailing how the actor had 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), Nivine reshared the clip in which the Good Will Hunting star can be heard asking her, “Nivine, why did you unmatch me? It’s me.” Unsurprisingly, the TikTok quickly blew up. I’ll let you make your own judgements, but there’s a cockiness to his tone that’s shiver-inducing and most people had one of two thoughts – the first being, “oh, how embarrassing, Ben”, the other “hmm, that’s kinda creepy”. 

@nivinejay

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

? original sound – Amir Yass

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

Fast forward to today and the internet has since moved on from the clip with all attention now focused on love’s young dream, aka Bennifer 2.0 (I personally prefer Jenjamin as a reboot name but whatever). TMZ recently revealed that the newly re-minted pairing hasn’t come as out-of-the-blue as fans might think though, with Ben seemingly 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 has apparently been laying the groundwork for months already, with the first correspondence being sent as far back as February. 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 emailed 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 (see here if you need a refresher).

As it turns out, this isn’t the first time Ben has shown himself to be more than a little awkward when it comes to flirting either. In fact, it seems he hasn’t updated his schmoozing skills since he first set his sights on JLo back in 2002 when he took out a series of half-page ads to say 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 really, who spends $15,000 to fix someone’s reputation unless they have their eyes on a different prize. The weird thing is, much like his heart-holding pen (I really hope this is a metaphor, otherwise it’s even more grim), the move worked. A few weeks later, Bennifer/Jenjamin was born.

Asked his thoughts on whether the famous twosome will rekindle their romance (now over 17 years on), Affleck’s pal Matt Damon was careful not to give much away, telling The Today Show that “there is not enough liquor in the world for you to get me to say something about that”. Describing it as a “fascinating story”, he very diplomatically said that he “loves them both” and sincerely hopes it’s true. His words say one thing, the subtle smirk he gives the camera another, and quite frankly, that’s all the fuel we need to continue speculating.