Mailbag for November 10, 2023

The guilt of absence, Travis and Taylor NDAs, Mimi vs JLo, why Drake (?), and working with friends.

(Photos: London Entertainment/John Salangsang/Matt Baron/Shutterstock)

Dear Squawkers,

Getting a little personal to start this week’s mailbag because one of the ways we can expand on our work here at The Squawk is to provide some insight into what our jobs are like. My job is to be a culture critic and an entertainment reporter and over the years, with social media and the 24-hour news cycle, it can feel like you always have to be on, and connected, and ready to turn up whenever some shit goes down.

I’m halfway around the world right now, literally. And I’m gone for a month. And the strike just ended, which means that Hollywood will be balls to the wall for the next four weeks or so to make up for lost time, an aggressive push to promote movies and TV, etc, before the year is over. Which means that my colleagues at ETALK will probably be busier than ever as junket invitations and interview opportunities will be coming at the media from all directions after such a long pause.

That was my second thought when it was confirmed that SAG-AFTRA and AMPTP had come to an agreement. My first thought was… YES! It’s over! They’re back to work, we can work! And then came the guilt. Because while I can definitely work on LaineyGossip, I won’t be able to help out on the television side. Which is when the guilt set in, which is so strange, because where does this come from?! So many of my friends and colleagues have felt the same way. Would it surprise you to know that almost all of them are women?

But let me stop my martyr performance before it even starts. Because I will tell you, that guilt didn’t last long. A few years ago, I wouldn’t have been able to shake it. Now, though, maybe with age and experience, I get over it pretty quickly. Then again, this is a learned practice. I had to learn to let it go, and to stop taking on guilt that, really, doesn’t belong to me. If this experience resonates with you, if in your job and in your work, you have also been burdened with a guilt that doesn’t belong to you, please share in the comments below. Pretty sure we’re not alone in this.

Now to your questions.  

Question from Kiki:

I'm so curious about Taylor and Travis and initial logistics. Are NDAs typically signed before they even have a first date? What kind of legal and privacy maneuvering has to happen before two super famous people can hang out for the first time?

Lainey’s Answer:

We’re probably going to fight about this but… I don’t think Taylor Swift had Travis Kelce sign an NDA. Am I naïve? Am I losing my edge?

Before you write me off, this isn’t coming from any kind of romantic illusion about TNT, as Sarah likes to call them, and pushing aside the possibility of an NDA because it would ruin my fanfic. There’s nothing fantastical about my rationale at all. Rather it’s about the way I read Taylor and Taylor’s performance of her celebrity. Yes, of course, she is as controlled and as strategic about her image as any celebrity ever was. But that’s also why, in the maintenance of that performance, I don’t think she’s passing around NDAs to her potential suitors.

Because her whole shit right now, in her current era, is about being chill. Up for anything. Drinking out of plastic cups at the football game and high-fiving people in the suite. Sending over an NDA before the first date kinda undermines the character she’s playing right now.

The more interesting question, though, isn’t Travis and an NDA but all the supporting cast in their rom-com. The other WAGs, the adjacents who are orbiting their romance. Are they being presented with NDAs before they show up at her NYC home for the viewing party that she threw for KC’s game in Germany? I don’t know that she has to take it that far to ensure privacy. Were they asked politely either by Taylor’s security or other members of her team not to post photos without permission? Sure. Probably. I buy that. But was there a piece of paper presented to them to sign when they stepped out of the elevator? I’m not sure she’d have to take it that far.

And then you have to consider what it’s like for those people. Here they are, one minute they’re a little community of supporters travelling to and from the games alongside their partners and the next minute, one of the biggest popstars in the world is inviting them to hang…

Like there’s also the psychology of what it’s like for those people, too, you know? Because most of the time, when you’re in that moment, you’re not thinking about how you can get this info to TMZ, you’re thinking instead about how you can figure out a way to repeat this opportunity next weekend. And none of them wants to fuck with the chance that they might not be invited whenever Taylor decides to open up her home again and allow them through the doors.

I’m saying this with confidence because I have been there. Maybe not at Taylor’s level but I’ve been to an exclusive party or two in my life, something very private, with celebrities all around, and even I, as a gossip columnist, have restrained myself from creeping a photo from the corner because I did not want to risk missing out the next time.

Taylor Swift watches next to Donna Kelsey in the second quarter as the Kansas City Chiefs play the Chicago Bears at Arrowhead Stadium in Kansas City, Missouri on Sunday, September 24, 2023. (Photo: Jon Robichaud/UPI/Shutterstock)

Are there instances when very famous people do the NDA thing? Of course. Beyoncé is an example. But at the same time, is Beyoncé ever going to fucking invite the wives and girlfriends of a bunch of football players into her home? Please. Beyoncé performs fame differently than Taylor. Taylor, right now, is the girl who is actively befriending the other WAGs. In making that choice to live this way, at least for the moment, she can’t have it both ways. Which is why I don’t think she’s trying to.

Question from Alice:

Lainey appears to love both Mimi (Mariah Carey) and JLo. Can we revisit the Mimi and JLO feud and if push came to shove - what side would Lainey actually be on? Like, is Lainey more Team Mimi or Team Jlo? I went down a rabbit hole and read that JLO allegedly "took" songs from other female artists (Chante Moore, Christina Millian, Ashanti, Brandy). Does this explain why JLo doesn't have female celeb friends? Mariah actually does.

Lainey’s Answer:

You are, of course, referring to the classic work of art called “I don’t know her” …

…which is a film we have all watched many, many times and will continue to watch many, many times until we are dusty and forgotten.

Mimi or JLo? If push came to shove? Sorry, but I will borrow from both of these women here and refuse to answer! And the reason I refuse to answer, aside from fear, lol, is because we need them both. No one wins when there is one or the other. The reason why “I don’t know her” is such great gossip is because they both exist, and they both exist spectacularly. That’s what makes it a hall of fame moment. We’re not dealing with a A-lister stomping on a D-lister. We’re dealing with two superstars in the same shady space, and the molecules in the ecosystem that have to adjust themselves around their alleged disdain for each other. It wouldn’t matter as much if they weren’t at the levels that they occupy independently. So, with all due respect, to even suggest there could be a side is to undermine the only side that we should protect and honour – which is the side of gossip. I am on the side of gossip, period.

As for the rabbit hole, yes, JLo probably did take songs from other artists. Yes, that is the reason some people don’t fuck with her. But that’s also not the whole story of JLo’s fame. She is relentless, she is a hustler, she is better at being famous than so many people who are so much more talented. And that is unrelated to why she doesn’t have any female celebrity friends. Does Mimi have female celebrity friends though? She is friendly with many celebrities, but I don’t know that we can say that she hangs out with a lot of female celebrities. Neither of them does, really. JLo used to be seen a lot with Leah Remini but it’s been a couple of years for those two and there’s never really been any exposed tea about why they’re not together as much as they used to be. But you could say the same of Angelina Jolie who also, for the most part, doesn’t perform celebrity friendship the way others in Hollywood do. With these women, is it necessarily about them…or is it about the opting out of celebrity squadding?

What I can say about JLo, and this has been obvious for years, is that she does have a very close circle of friends who are women and they are not famous. She is also super tight with her family. And sometimes, with some celebrities, that’s an active choice. We have gossiped a lot about the transactional nature of celebrity friendships, sometimes we have even judged them. When JLo was with Marc Anthony, for a while there she rolled around in a crew that included the Beckhams, Will and Jada Pinkett Smith, and Tom Cruise and Katie Holmes. Remember that? Tom and Katie’s sudden split seemed to bust up that weird caravan of couples. And some might say that’s a good thing.

Jennifer Lopez, Marc Anthony and Leah Remini return to the Hassler Hotel in Rome, Italy after attending Tom Cruise and Katie Holmes' rehearsal dinner on November 16, 2006 (Photo: London Entertainment/Shutterstock)

Question from Lil:

This is something I've been wondering about for a long time so I'm asking about it here, if even only for my fellow Laineyphiles' comments. Why is Drake? He's a mediocre rapper/singer who has no variety and from all appearances is a total douchebag (no offense to actual douches that serve a valid purpose). Maybe Drake is a better actor than musician, of this I have no knowledge never having watched his acting. I just don't understand why Drake is so popular. Fully acknowledge this could be because I'm old. 😃 My rap taste leans to Kendrick Lamar and Eminem.

Sarah’s answer:

I will answer this because I, too, wonder why Drake? all the time! Every time he’s in a headline, I am like—why is this guy taking up my time? I have never in my LIFE liked a Drake song. I know a lot of people do, he’s very successful! But I can usually find ONE song to like by an artist, but with Drake…nothing. Just zero response to everything he has ever done. So I have actually thought about this, because I find his music so bland, so plain oatmeal, and I don’t get why HE is one of the biggest rappers right now.

I guess he’s kind of like Justin Timberlake, in that he was on a teen show that made him popular with kids, and then he parlayed that into a music career, he had a built-in fanbase when he made the leap. But what I have really landed on is this—as you said, your rap taste leans to Kendrick Lamar and Eminem. They are both very talented rappers and artists. But they’re challenging. Run The Jewels is challenging. Megan Thee Stallion is challenging. Going back in time, the Fugees and Tupac are challenging. Bad Bunny is challenging. Tyler The Creator, Childish Gambino, Lil Nas X, Roddy Rich, Cardi B—they’re all challenging.

By challenging I mean, they have complex musical influences that incorporate a lot of different sounds—especially someone like Bad Bunny, who brings a truly global sound to hip-hop—they may have catchy Top 100 hits, but their lyrics can be loaded, touching on hot-button issues and real shit affecting real people’s lives—poverty, injustice, racism. There are extraordinary artists, lyricists, and rappers working in hip hop, using the medium to tell complex stories about complicated people in complicated times and places.

Drake attends the 'Euphoria' TV Show Premiere in Los Angeles on June 4, 2019 (Photo: John Salangsang/Shutterstock)

Drake is not that. Drake is the suburbs. He is safe. He is not challenging. His lyrics go in one ear, and out the other. The only time anything he says sticks is when he’s talking shit about a woman whose name he needs to keep out of his mouth. Drake is hip-hop for people scared of hip-hop. And a LOT of people are scared of hip hop. And so, Drake as the “#1 rapper” is born.

Lainey’s Answer:

Drake is from Toronto, I am from Toronto. I am obliged to care about Drake…and I do. I agree with Sarah in that Drake’s music isn’t necessarily, um, deep. But I’m into it. My favourite Drake song is “Find Your Love”; I will always have time for “Find Your Love”. My second favourite Drake song is “Passionfruit”. I have a working theory on Drake and I’ll be writing about him when I can get the piece out of my head and onto the page but for now, what I’ll say is that the answer to “why Drake” is because he, like JLo, is very good at being famous. Drake is excellent at media manipulation. He is the master at creating a viral moment. And he can be funny. His problem is that he doesn’t actually value his actual skill set. More on this when I can figure out my thesis. 

Question from Erica:

Stephanie's piece on Tyler Perry is just so, so good, and it made me think of a question I've wondered about off and on for years: how do you find new writers for LaineyGossip, and what are you taking into consideration when adding a new voice? (To go back to the Stephanie example: she also covers Bravo/The Real Housewives. Were you looking for someone to cover those, or did you come across Stephanie’s work and find things that make sense for her to cover?) LaineyGossip has such a distinct voice and point of view, and writers for the site seem to seamlessly advance the LG brand and voice while bringing their own deeply specific perspectives. It’s really cool to watch.

Lainey’s Answer:

THANK YOU! We love Stephanie’s voice on the site – and yes, reality television is her beat, along with Maria who is also an expert on Housewives and the Bravoverse. Stephanie and I used to work together on The Social, the talk show in Canada that I co-hosted for ten seasons until recently. She was a producer for about a year and a half and then she moved over to ETALK before leaving for another opportunity. So I was familiar with Steph’s storytelling, her insight, and her experiences. Steph was also writing her on blog on the side, and I liked her work. So when the time was right, we hooked up for a meeting and talked about her gossip interests, I thought she’d be a valuable addition to the site, and Sarah and I discussed it and we moved ahead.

What I appreciate most about all the writers who contribute to LaineyGossip is that they all have their own lens through which they’re processing celebrity stories. Stephanie has shared a lot about her dating life, being a single mother, the anti-Black racism she’s encountered, and her mental health. Who we are shapes how we view celebrity and what we’re trying to do on the site is to present celebrity analysis through as many lenses as possible.

Like Steph, most of the writers who are featured at LaineyGossip are people I’ve met through the Canadian media industry, with the exception of Sarah, who is American. That includes Duana, Sasha, Hayley, Maria, Joanna, Melayna, and Cody. I had professional encounters or working relationships on one level or another with all of them in advance of them joining the LaineyGossip team. Basically, we’re all trying to collaborate with our friends, and this has really become standard practice in media/comms/arts/marketing over the last 15 or 20 years. Co-writing and co-directing teams are common in Hollywood now. Friends are forming production companies with each other. Influencers are starting brands together. So I’m coming to a bigger point…

It used to be that we were told – never work with friends, don’t go into business with friends. In certain cases, sure, it’s a bad idea. But while I acknowledge that my example might be narrow, I personally have observed that in creative spaces, especially among women, we’ve seen great results. The key is communication and honesty, and I know this is a basic bitch thing to say. But sometimes the basics get missed, or they’re just not appreciated enough. For example, maybe it’s because we all come from creative backgrounds, but feedback isn’t the issue that I’ve heard it can be in other industries – because with writers, we have all at one point or another hated our own work anyway, lol. 

My favourite piece of advice that I try to share with as many people as I can is something Duana passed on to me from someone who passed it onto her: “You can’t fix nothing.” As it applies to writing, this refers to your first draft, which is often the hardest to get out. Because getting started is, for many of us, the biggest challenge. Because it’s perfect until you begin, you know what I mean? But then you’re sitting there staring at a blank page and then the fear creeps in and you’re like… ugh, I suck, I’ve got nothing.

Right, but then you can’t fix nothing. Nothing is nothing. But a terrible first draft, at least, can be improved upon. So to go back to feedback, in my experience working with all these amazing writers, we’re not sensitive to the feedback. We want the feedback – it helps! We KNOW it’s bad, what we want is to make it less bad. Nobody is sitting here thinking we’ve just written a masterpiece. Quite the opposite, actually.

I’ve probably drifted here from what you were originally asking, but your question was about the different writers representing their unique voices on our site. And you can’t get there, with writing, and figuring out your voice, unless you keep writing and you keep fixing the shit that you’re writing. And it’s way better to do that if you’re not alone.

Sarah’s answer:

Nothing I’ve ever written has been bad, I don’t know what Lainey is talking about with this “feedback” nonsense. No, seriously, I go places, film festivals, tons of screenings for various critics’ groups I belong to, I’ve done some panels at various comic/fan conventions. I meet people, and I listen to them. If they’re interesting in person, I look up their work. If the work doesn’t suck, I file their name in my mental rolodex under “someday”.

Someday, I hope to extend to others the opportunity Lainey extended to me, to share this platform with new voices. Growth comes slow but steady, but it does come eventually.

So on that note, thanks for reading our work and for reminding us that we’re not alone. Please feel free to squawk your feedback at us any time.

Keep squawking, keep gossiping,

Lainey and Sarah