Jennifer Lopez stepped out earlier this week with her daughter Emme. The first set of shots that was released wasn’t all that remarkable – she looks great in a summer dress, classic JLo sunglasses, the hair is pretty undone, by her standards… nothing much to say, which is why I didn’t. Until now. 


Because there’s another set, and in this set a shot of her left hand, and on that left hand what appears to be a new ring. A large new diamond ring? TMZ points out that she ends up turning it around so that it’s facing her palm once she figures out the paps were shooting her. 

Does this…?

Is it…? 

Are they…? 

I mean, this is JLo. It’s not like she can’t buy her own diamonds and buy her own rings – I know those aren’t her lyrics but the spirit of “Independent Women” certainly applies to her. But also… it’s JLo. And JLo loves love and getting engaged. And we’ve been on Bennifer engagement watch ever since, well, ever since… 

A year ago, almost exactly. When her last engagement officially ended. That’s right, it was pretty much a year ago that JLo officially confirmed the end of her engagement to Alex Rodriguez and as we know now, Ben Affleck was waiting in the wings and since then, gossip has been good. 

They just bought a property together. Their families appear to be all connected. Is it time? Is it finally time to do what they were supposed to do 20 years ago? Bennifer’s first engagement was in November 2002. Which means we are six months away from the 20th anniversary of the day he proposed to her (the first time, if there’s been a second time). What if they mark that anniversary by actually getting married????????????????????


Maybe we shouldn’t get ahead of ourselves. It could just be a ring, not an engagement ring. Maybe she’ll clarify all this in her next newsletter? 

About this newsletter – you know about it, right? If not, let me explain, briefly. 

Remember back in February the Valentine’s Day gift that Ben gave to JLo… and all of us? He recut her “On My Way” video and dedicated it to their love – and Matt Damon, LOL, because for some reason, Matt showed up a lot in the piece. An amazing piece of gossip that I will forever be grateful for. Click here to revisit that post. 

Anyway, before she shared the video with the world, JLo actually told her fans about the video on social media and asked them to “keep it ON THE JLO”. 

ON THE JLO is the name of her community newsletter. Yes, she has a newsletter (free to subscribe)– there have been two sent out so far. For someone as famous as JLo, and few are as famous as she is, the newsletter is…well… pretty lo-fi. Which is both surprising and not at the same time. Because given her Hollywood status, you’d expect it be top quality only for JLo. And yet it’s also kind of on brand for her because part of her brand, at least the one she tries to sell, is that she’s still “Jenny From the Block” and super accessible. And the newsletter is accessible, both in content and construction. 


Like we’re talking the most basic bitch layout ever, using a pretty basic newsletter program, so basic that I would almost believe that she did it herself because, like I said, you don’t need a graphics or tech person to have worked on it – it’s 2008, max 2010, a throwback to the beta version, for example, of Goop. Clean, straightforward, nothing fancy, and definitely no glow. In fact, it could use a glow-up, LOL. Except I actually don’t want her to glow it up because it’s amazing in its simplicity. 

The simplicity makes the content stand out. And the content is… 

Like a diary? Journal entry? I know it sounds like I’m getting paid by ON THE JLO to promote this sh-t – and believe me, I wish I was – but it’s worth the free subscription just for the study in celebrity-to-fan engagement. The whole point of ON THE JLO is to make her fans feel like they have special access to her, so the fact that the whole thing IS so stripped down and lo-fi in a world where product placements and mass over-produced and slick presentation decks are inescapable makes her approach that much more effective, especially when she’s sharing pictures of the books on her nightstand and a video of her taking a bath that … yes… WAS FILMED BY BEN AFFLECK. 

You want to watch? I know you do. The link is here and yes, you have to sign up, so up to you if you want to share your email address with her but in exchange, what you’re getting is Ben Affleck’s camera work, trailing her body in the bathtub as she looks into his lens with adoration while he’s shooting her with equal adoration. 


It’s both performative and intimate and it is 100% GREAT FOR GOSSIP, and all part of this newsletter that, dare I say, feels kinda…radical?! Like what is she even doing with all this sharing, it’s not like she needs to! This is completely unnecessary, she’s already JLo. She’s made it. She’s all of it. But still, she’s still out here hustling, guaranteeing fan loyalty with a level of connection that celebrities at her level seldom bother with. 

So. To go back to a possible engagement…

If there is one, I’m hoping the confirmation doesn’t come in the usual way. I’m hoping she “keeps it ON THE JLO”. I’m hoping we find out in the newsletter – because, again, the way she’s serving the gossip on the newsletter is where I want it to live. 

Also attached - Ben Affeck leaving JLo's home in LA yesterday morning.