It’s no secret that Madonna has mentioned on numerous occasions in the past that she often finds herself drawn to younger men post-Guy Ritchie because they’re the only ones who seem to be adventurous enough for her. Open and willing to try new things (Britney Spears, too, knows something about that with her own younger fiancée, Sam Asghari).
And it’s true, when you’re an “older” woman who hasn’t lost her soul or chutzpah to capitalism and The Man (by instead becoming capitalism and The Woman), it’s more of a challenge to find someone in your own age bracket to identify with. Someone who hasn’t surrendered their joie de vivre entirely. And, more to the point, someone who isn’t already divorced with multiple children that you don’t want to fucking take on. God or whoever knows that Madonna already has a litter of her own and doesn’t want to engage in any Yours, Mine and Ours shit.
A movie, incidentally, that plays just as heavily into the plot of Licorice Pizza as waterbeds. Madonna revealed no spoilers, however, when she posted a series of images of herself at a private screening and captioned it, “Saw the movie Licorice Pizza! Omgggggggggg!! Felt so inspired I had to clean the theater.” Considering Madonna’s own upcoming as-of-yet-untitled biopic—and her dilemma with casting—her enthusiasm for the film is certainly understandable on this front (and on the front where her “greatest love of all,” Sean Penn, has a part in it). But the underlying ardor for it can only be a testament to her own comprehension of what it is like to be the older woman in a relationship. Where sometimes the tradeoff for more agile dick is the immaturity that comes with it (you know, like pantomiming masturbation with a gas can).
Madonna, having been “linked” to her backup dancer Ahlamalik Williams since roughly 2019 (though he was already dancing for her on 2015’s Rebel Heart Tour), is no stranger to the May-December romance. After her divorce from Stick-in-the-Mud Ritchie, she had dalliances with Jesus Luz (a model), Brahim Zaibat (also a backup dancer for her, and theoretically the person who inspired “Unapologetic Bitch”—though that also could have been Timor Steffens) and Kevin Sampaio (another model).
Her penchant for the “attractive but a bit daft” is in contrast to Alana Kane’s (Alana Haim) eventual acceptance of Gary Valentine (Cooper Hoffman) as more than “just” a friend. Theirs is an ever-blossoming romance based purely on friendship as the foundation, whereas Madonna always seems to be most allured by the “aesthetic” of a younger man that draws her in.
Williams, however, is more of a departure from all the rest. Not “conventionally hot,” there appears to be something else to their dynamic. Maybe he rolls with the punches more than the rest, or knows better than to act “overly” attached—something that got Jesus Luz booted from Madonna’s fold (no, that’s not a vaginal reference, though it definitely works as one). For all we know, part of Madonna’s dating only younger men could also be a larger aspect of her statement on breaking down the long-standing stigmas against older women, including “being allowed” to date younger men in the same way it has always been permissible for older men to “date” (read: fuck) younger women.
To this point, the May-December romance when the woman is the December is inherently less creepy (save for the example of Norma Desmond and Joe Gillis) because women are rarely the predators or pursuers in such scenarios. What’s more, women are more often in it for a relationship as opposed to the simple “thrill” of fucking someone younger and hotter. And yet, even still, people are more offput by the sight of a “hag” with a “boy.” Because, as Madonna has pointed out time and time again, society would rather see a woman kept down, put out to pasture and hindered from any sense of joy or feelings of desirability past the age of forty. But if Madonna and Alana (a fitting rhyme) have anything to say about it, such outmoded views of women and who is “appropriate” for them to date won’t last forever.
