Celebrity Dating Gossip Is Getting Me Through This Pandemic

From Brad Pitt and Alia Shawkat (maybe) getting cozy during quarantine to Ben Affleck and Ana de Armas’s endless paparazzi walks, I can't get enough of celebrity odd couples.

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Over the past couple months, very few things have brought me any lasting sense of joy or pleasure — at least, not anywhere near the level I’d grown used to pre-pandemic. Dark, sorry, but true! I’m depressed, worried about the future of my job and of my industry, and riddled with class anxiety. But I’ve got a few old standbys that bring me precious moments of comfort these days: grabbing to-go cocktails from my favorite neighborhood bars, working on bad quarantine art and trying not to care how bad it is, taking weed gummies, and — thank god! — celebrity gossip.

One of my current favorite nuggets: Brad Pitt and Alia Shawkat are hanging out (and maybe dating???). Last fall, in the midst of a fawning press cycle for what would become his Oscar-winning role in Quentin Tarantino’s Once Upon a Time in Hollywood, Pitt was attending comedy shows and art gallery openings with Shawkat, sparking dating rumors. Right before lockdown, in March, they went to a concert together and stopped at an In-N-Out afterward. Dreamy!

The tabloids have been all over Brad and Alia — not only because Pitt and his relationships have starred in gossip pages for decades now, but because Shawkat is nowhere near as famous as he is, and she’s about 25 years his junior. She’s also queer, and visibly so, having rocked a shaved head or a short cut for a while now; once the tabloids caught on, headlines have frequently reduced to her a “bisexual actor,” presumably for the titillation factor. What must Jennifer Aniston think?? Even before the much-dissected run-in at the Golden Globes between Aniston and Pitt earlier this year, Star and People and the like have refused to let poor Jen move on with her life. (Also, as Who? Weekly’s screamingly funny episodes during the pandemic have made clear, the tabs are truly desperate for content right now.)

A lot of the gossip blogs identified Shawkat only as a “mystery woman” early on in their friendship, until it became wider knowledge that the person Brad’s been growing close to is an actor best known for her roles in Arrested Development and Search Party, in addition to being a writer, musician, and artist. Anyone who doesn’t pay much attention to pop culture beyond the blockbusters might consider Shawkat the way a bland, much-maligned girlfriend character is treated on Arrested Development: Her?

But Shawkat, though she’s only modestly famous at this point, isn’t bland at all. She’s an excellent comedic performer with memorable turns in shows like Transparent and Broad City, and a writer whose credits include 2018’s Duck Butter, which both charms and disturbs. The film, in which she also stars, sees her dating and sleeping with a(n increasingly unhinged) woman; it’s one of the many queer characters she’s played. For that reason and for so much more, I find it absolutely delightful to imagine Pitt, who sources have said appreciates Shawkat’s work, watching her weird gay film in which someone (spoiler) shits in a pot and threatens to smear it around everywhere.

Brad and Alia’s whatever-ship is one of my favorite kinds of celeb pairings precisely because they’re seemingly such an odd couple: the age gap, for one thing, and the discrepancies in their levels of mainstream fame, but also their varying positions in the entertainment ecosphere. A few others are kicking around the gossip cycle now too, including my ultra-faves Gina Gershon and Ben Sinclair. (More on them later.) I love whenever two people from very different but equally beloved parts of my cultural consumption find something of value and beauty in one another, and not only because I take them as yet more evidence that I have great taste. ;) More so, I just think it’s lovely whenever anyone, celebrity or otherwise, finds connection across boundaries that were maybe not quite boundaries at all.

Ever since Michael Paterniti’s iconic GQ profile of Pitt from 2017, which was Pitt’s first major interview since the demise of Brangelina, I’ve been back on the Brad train. The photos of him rolling around in various national parks for the magazine spread — ugh! They’re gorgeous; he’s gorgeous. He always has been, really, but toward the end of his marriage with Angie, he’d started looking pretty rough. (Of course, then and now, I have no real insight into Pitt’s private life and am therefore ill-equipped to say whether he’s actually a Good Person. Reports that he hit his son on a private jet, which emerged during his bitter postdivorce custody battle with Jolie, for one thing, are extremely troubling. For whatever it’s worth — and in the American criminal justice system, it’s not necessarily worth much! — an investigation into the abuse claims was closed in 2016 with no findings of wrongdoing.)

Now, sober and retrospective, with a refreshed and youthful vigor, Brad’s back and better than ever (or so it seems, at least). He’s realized, perhaps, that he’s really a character actor trapped in a movie star’s body, whose best work has always been in scene-stealing supporting roles. I could easily imagine he’d feel more at home, at this stage in his career, dating someone who’s doing interesting work at the margins of the mainstream — one of the reasons why I kinda hope that, even though they haven’t confirmed it and sources keep telling the tabs there’s nothing romantic or sexual going on, Pitt and Shawkat aren’t merely best buddies. (If they are, though — still love that for them!)

Like Kenzie Bryant at Vanity Fair, I’ve been having fun filling the void in quarantine asking myself (and all my friends) whether these guys are actually dating. Obviously we should tread carefully here; the tabs have worked themselves into a vicious frenzy over since-quashed dating rumors about Pitt’s friends before. But that doesn’t mean we should ignore enticing evidence. Last month, Shawkat was spotted biking out of Pitt’s gated community in Los Angeles — on her birthday! — which suggests at least a friendliness strong enough to constitute in-person hangs mid-quarantine. Hopefully, if they’re following the spirit of social distancing, they aren’t seeing many other people, which suggests quite a close bond indeed.

I’ve been trying to figure why the idea of this couple tickles me so much, and I think a number of different things are going on here: For one, I’ve always been hopelessly in love with Brad, first as a closeted lesbian — and even now, as a fully out lesbian — in much the same way I used to be in love with Leo (though my Leo lust quickly died after he grew out of his twinky phase). Both men weren’t just handsome as young stars — they were pretty, their gold-standard masculinity spiced up with a dash of the androgynous. I think I was drawn to Brad’s beauty at a time in my life when I thought men were the only kind of people I could desire. I always liked him best when he played a strange but sexy weirdo (the Ocean’s trilogy, Burn After Reading) or when his leading roles were ridiculous and campy and therefore kinda gay (Interview With the Vampire, Troy).

While Leo has grown more bloated and remained dead set on never dating women older than 25, Brad has only gotten more handsome. He also seems to morph into a version of whomever he's dating at the time (classic lesbian behavior). Leo’s dalliances with a parade of skinny, young supermodels only depresses me, but Brad’s potential hookup with a younger woman only delights. Why?

In many ways, a Brad/Alia pairing would be a regurgitation of the oldest celeb story on earth, more evidence for a thriving patriarchy: A powerful man dates a much younger, less powerful woman. But for me, their relationship (whether friendly or otherwise) troubles an otherwise dated and disappointing narrative. Yes, Shawkat is young and beautiful, but she isn’t exactly the type of woman we’ve come to expect in the arms of aging actors in the midst of their midlife crises. She’s in her 30s; she’s Iraqi American; she’s not tall or ultra-skinny or blonde; she’s queer; she’s cool.

While Pitt might be more famous, Shawkat has a small but significant cultural cachet in the art worlds of LA and New York. It may seem like she has more to gain from a relationship with an extraordinarily wealthy and famous man — and therefore more to lose — but Pitt stands to find firmer footing in more alternative and experimental spheres, which is where he seems to be steering his lifestyle as well as his career. I have to imagine he’s not just another geezer dating (or friend-dating) someone younger because he’s afraid of his own mortality, but that he genuinely values Shawkat for her mind and artistic imprint on the world. That only heightens my estimation of him, tbh. Again — I could be totally wrong here! But a girl (especially a depressed one in lockdown) can surely dream.

A confession: I also might be a little more invested in this potential relationship than the average fan of one or even both of these celebrities because I’m also in a relationship with a significant age gap. Ours is the same as Alia and Brad’s: about 25 years. Even though I know that lesbian relationships with age differences don’t carry quite the same stigma or baggage as older guy/younger woman couples — which are often stigmatized for good reasons — I can still feel weirdly sensitive when anyone slams prominent May–December relationships. Before I started dating my girlfriend, I probably would have been grossed out by Florence Pugh and Zach Braff, for example. Now I can’t help but feel sympathetic for Pugh, who’s tired of the constant judgment she’s facing from her fans.

I find it fascinating at what ages and in what contexts our internal alarm bells start ringing. To a lot of people, Pugh, at 24, seems much too young to be dating a 45-year-old. But would her maturity be more credible at 25? At 28? Everyone’s comfort levels are going to be different, but I know that my own sense of what’s appropriate when it comes to seemingly mismatched relationships has shifted since I fell in love with someone twice my age. (I also recognize that people’s negative responses might be somewhat different if the 45-year-old in question here weren’t, specifically, Zach Braff.)

Another celeb couple who’s brought me and many others some much-needed joy during this pandemic has been, of course, Ben Affleck’s blossoming relationship with Ana de Armas. He’s 47 and she’s 32 — a gap for sure, but not a huge one — and their attention-grabbing antics during lockdown have led some to write them off as a publicity stunt. I have no idea whether they’re wearing matching half-heart necklaces in earnest, and I don’t really care whether the relationship lasts, but you know what? I’m here for #Benana. Can’t really fault these maniacs for giving the people exactly what they want.

A relationship I genuinely believe in, though, is the pairing of actors Gina Gershon, 57, and Ben Sinclair, 36. The star of lesbian classics like Bound and Showgirls and the actor, writer, and director responsible for HBO’s High Maintenance haven’t been super public about the status of their relationship, though Sinclair makes frequent appearances on Gina’s Instagram, and they’re currently riding out quarantine together in their shared home. What a delightful partnership!! It just makes me happy whenever anyone finds love despite or because of their differences, whether generational or otherwise — and especially when those connections flout traditional norms. In Sinclair and Gershon’s case, we don’t tend to see older women with younger men — and as a huge fan of older women generally, I love when others appreciate what I appreciate. But it’s not like Sinclair is doing Gershon a favor or anything. I mean, I love him, but he is just okay-looking while she is smoking hot!!!

That’s what I really enjoy about all these seemingly incongruous pairings, which (however slightly) scramble traditional power dynamics and offer us bystanders evidence for different kinds of love. I’m not gonna go so far as to say these good-looking, mostly white and heterosexual celebrities are queering anything, but they aren’t following the strictest of social scripts, either. We need not reward any famous people for their bravery in dating other famous people. But we can idly imagine how good the sex is. And right now, I’ll take that. ●

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