Perhaps of all the celebrity women who can relate to a song like Sabrina Carpenter’s “Please Please Please,” Britney Spears is the most equipped to do so. Even though it seemed like, at the beginning of her career, the “dating gods” smiled upon her with someone who was as then cachet-laden as Justin Timberlake. That notion didn’t last very long. What’s more, although Timberlake’s behavior and aesthetic should have been embarrassing at the time, it was instead the height of late 90s/early 00s cool (obviously, retroactive embarrassment caught up). Complete with Timberlake’s signature yellow “ramen hair” and, yes, the blaccent that Spears trolls so well in her 2023 memoir, The Woman in Me.
During their approximately three-year relationship, Spears was still in a cushioned period of being “America’s sweetheart.” Alas, once the two broke up and Timberlake went on what amounted to a “she’s a slut” campaign (or, as Spears put it, she was portrayed “as a harlot who’d broken the heart of America’s golden boy”), everything changed for Spears. The media attention she was getting only got worse and worse in terms of fixating on her “skanky” clothing choices and her so-called “bad girl behavior.” And it seemed that Spears, in part, simply decided to fulfill the image that the public had of her—in short, to give the people what they wanted.
Thus, her first fling after Timberlake (if one doesn’t count the dalliance that catalyzed their breakup, Wade Robson) was none other than Irish bad boy Colin Farrell (whose image has softened since that era). Granted, Spears wouldn’t have described it as a fling. Instead, she noted, “Brawl is the only word for it. We were all over each other, grappling so passionately it was like we were in a street fight.”
Although that brawl was short-lived, it didn’t take Spears long to find another fling opportunity that she tried to parlay into “till death do us part”: Jason Alexander. As the media ribbed at the time, no, it wasn’t George Costanza that Spears had eloped with, but some backwater childhood friend she found herself in Las Vegas with during a post-New Year’s Eve bender. “Forever” was hardly the word for their fifty-five hour marriage though. And Spears’ parents were quick to swoop in and do “damage control” by demanding that she get the marriage annulled.
And so, by early 2004, despite Spears’ scant “body count” on the dating history scene, everything had thus far fallen into place to align with the Carpenter-penned plea, “Please, please, please/Don’t prove I’m right/And please, pleasе, please/Don’t bring me to tеars when I just did my makeup so nice/Heartbreak is one thing, my ego’s another/I beg you, don’t embarrass me, motherfucker, oh.”
Unfortunately, Spears had yet to endure her biggest embarrassment of all: Kevin Federline. And just a few months after her drunken two-day marriage to Alexander, she would meet the odious “K-Fed,” arguably the worst thing that ever happened to Spears in terms of affecting her trajectory and leading it straight to a sham conservatorship. After beginning their torrid romance in the spring of 2004, Spears and Federline would be married on September 18, 2004 (though the marriage wouldn’t technically be legal until October 6, after the prenup was finalized).
The ceremony itself was a surprise to the guests who had been invited under the pretense that it was an engagement party. But lo and behold, Spears instead offered her guests a wedding befitting of her “Southern trash” vibe at the time. This extended to a menu of chicken fingers, fries and ribs, as well as having everyone change into matching pink Juicy Couture tracksuits once the (faulty) vows had been made.
The honeymoon period with K-Fed was quickly over after the back-to-back births of their Virgo children, Sean Preston (September 14, 2005) and Jayden James (September 12, 2006). It seemed Federline was more interested in going out and partying than staying home and raising a family (cue the lyrics, “Well, I have a fun idea, babe/Maybe just stay inside/I know you’re cravin’ some fresh air, but the ceiling fan is so nice”). This revelation dawned on Spears after it was already too late. The disappointment of the marriage, coupled with her postpartum depression, made for a lethal mental health combination. Ergo, all the stars aligned to paint her as having a “breakdown” (or, in other words, a normal reaction to the shit that was going on in her life). By November of ‘06, she had filed for divorce from Federline, just two months after the birth of her second son.
In the wake of Federline, there were more “randos” in between, including her AA drug counselor, John Sundahl, and paparazzo Adnan Ghalib, who Spears met soon after shaving her head on February 16, 2007. That relationship lasted until 2008…because, under the rules of the conservatorship, Spears’ dating life would be much more closely monitored. Something Jason Trawick didn’t seem to mind. That Trawick was already Spears’ agent seemed to indicate to Jamie Spears that he had her “best” “business interests” in mind at all times. Maybe that’s why he suspiciously made Trawick a co-conservator in 2012 (yet another reason many speculated him to be a “plant” in Spears’ life). Then there were the subsequent rando pairings of David Lucado (who cheated on her, quelle surprise) and Charlie Ebersol. This brings us to 2016, when Sam Asghari entered the fray after meeting Spears on the video shoot for “Slumber Party.”
While it seemed, for a time, as though Asghari might not be a shitheel ultimately using Spears as his cash cow like everyone else, things gradually revealed themselves to be slightly more sinister. That Asghari was also an aspiring actor only makes the following Carpenter verse all the more eerie: “I know I have good judgment, I know I have good taste/It’s funny and it’s ironic that only I feel that way/I promise ’em that you’re different and everyone makes mistakes/But just don’t/I heard that you’re an actor, so act like a stand-up guy.” Needless to say, Asghari did not. And Spears has since moved on to one of her worst selections yet: Paul Richard Soliz.
Hired as a “handyman,” of sorts, on her payroll, Soliz has a criminal record and possesses the same “deadbeat dad” aura of K-Fed. Whether or not Spears has learned her lesson and is just using him to fulfill her fetish for “felon dick” instead of actually trying to turn it into a serious relationship remains to be seen. But maybe, at this point, she knows better than to bother delivering the silent prayer, “I beg you, don’t embarrass me, motherfucker.” Her long-running taste in men pretty much seals the promise of that embarrassment. Which is why Spears might also be thinking to herself, “And we could live so happily if no one knows that you’re with me.”
