Taylor Swift has established herself as one of the world's most successful musicians of all time, with ten total Grammy Awards, an Emmy win, millions of fans worldwide, over 50 million records sold, a net worth estimated around $360 million, and looks that stop traffic wherever she goes.
From a distance, things seem to be great for Swiftie—all except on the boyfriend front, anyway. Her serial monogamy has become the punchline to countless jokes, from early days romancing a Jonah brother to short dalliances with the likes of Lucas Till, Taylor Lautner, John Mayer, Jake Gyllenhaal, Tom Hiddleston, Calvin Harris, Harry Styles, Conor Kennedy, Eddie Redmayne, Cory Monteith, and Zac Efron (that Billboard knows of, anyway).
Of course, with such a track record, it's almost surprising when Tay-Tay is caught without a boytoy—but it does happen, as evidenced by these 20 pics of the country-pop singer looking glum or unconvincingly happy without the requisite arm candy.
20 Tinder Profile
Taylor looks bright-eyed and bushy-tailed in this selfie, though the facade only lasts for about a second. Upon further examination, she looks a little sad, her eyes just a bit pink and swollen, like the weather might have reminded her of days gone by when the boys were swarming and she didn't tear up at the sight of old couples eating quiet dinners nestled into cozy restaurant booths.
19 Shucks
"Oh, well," Swift seems to be saying to herself in this candid, "At least it was good while it lasted." In all black, she looks to be mourning the passing of yet another boyfriend right out the slip-n-slide that is her life. But cheer up, girl, there are plenty more fish in the sea who want to be the subject of break-up tunes, no doubt!
18 No, You Don't Understand, Men Are The Worst
Here, Taylor Swift looks like she's taking out her breakup grief on a good friend after another one bit the dust. As if her friend didn't know, she's making the time-tested and time-proven point that, "Men, seriously, listen to me, men are the absolute worst." But when all of your dogs over the years have been mean and vicious, what does that say about you?
17 Rough Life
This photo of Taylor Swift looking totally lonely and depressed on a park bench in New York City—despite being dressed in a perfectly put-together ensemble—has become a meme in and of itself. Almost akin to Keanu Reeves famous bench pic, this one is more hilarious given Swift's enviable life and ability to attract attention everywhere she goes.
16 Cat-Lady Icon
Taylor Swift is pictured above having won the Icon Award at the Teen Choice Awards in August of 2019. The prize, though, comes with a surfboard looking dubiously resplendent in terrible airbrushing and a few awkward-looking cats. Was Swift really getting a prank played on her? Or is this a reference to her famous love of cats, which might be another reason the boys seem to flit away like butterflies being chased by cats?
15 On The Prowl
Swift's style has evolved over the years to match her music, which has transitioned from country to country-pop to pure self-indulgent pop. There's a bit of irony in the fact that Taylor might not like how much everyone peers into her laundry list of brief relationships, yet still produces song after song about herself dealing with her laundry list of relationships.
14 Believe It—Or Not
Once again, here's another photo of Taylor Swift in public, looking completely and totally satisfied that she's in the company of a best-girlfriend—in this case, Karlie Kloss, once again. The look of shock on her face must be echoed by all the guys she's gone through over the years, who would probably agree that she seemed pretty peeved at their departure in all those breakup tunes.
13 Comfort Food
Ah, comfort food—nothing quite fills the aching void in the heart and stomach that's left behind by yet another quick-in-the-door, quick-out-the-door romance like some good-old comfort food. But come on, TayTay, at least put some relish and ketchup on that hot dog! No one likes a bun that's dry as a bone!
12 Deep In Thought
The blank, spaced-out look on Taylor's face in this picture makes it look like she's suddenly realized that maybe, just maybe, the fact that all the boys in the world might not want to date her might, just might, not be because boys are the worst. But the contradictions only pile up from there, unfortunately, because if she doesn't need boys, why does she always find new boys?
11 Don't Need No Man
Taylor Swift's list of besties includes some of the hottest, most popular women in the world. On again and off again, though, she also gets into some fun feuds. Regardless, no one could possibly be left thinking she might want a man around when surrounded by the likes of Selena Gomez, Karlie Kloss, Emily Ratajkowski, Cara Delivingne, Blake Lively, and whoever else she's busy insulating her image with at any given moment.
10 Nobody Here Beside Me
On a cold, wintry day, it doesn't get much better than going for a stroll in the park, wrapped up in a warm jacket and scarf with the boyfriend on an arm keeping everything warm and cozy. Or at least, that's what it seems like Taylor Swift is reminiscing about with a twinge of regret that she couldn't get the last one to stick around through the colder months.
9 Wanna Go Upstairs?
Part of Taylor Swift's appeal used to be the down-home, country-girl type of attitude that was embodied through a bit of country twang, simple style, and classic good looks. All that is on display here, though her faux-hipster outfit and that look on her face must have been what countless unsuspecting future ex-boyfriends were attracted by on the back staircase (where the paparazzi don't lurk) up to her penthouse suite.
8 Best Friends
If nothing else, Taylor Swift has definitely earned her reputation as a master of earned media coverage. She's always in the tabloids, making news when she finds a new boyfriend, breaks up with said boyfriend, parties with her girl squad, or releases another record-setting record. But all the pics of her with besties like Karlie Kloss have ended up seeming a little forced over the years.
7 Who's There?
There are so many candid snaps of Taylor Swift walking across empty sidewalks online that it almost seems like she sets up times and places where the paparazzi can catch her looking pristine and unphased by the city bustle. The only problem is that all those pics end up making her look a little bit overdressed for being all alone.
6 Sweat It Out
There's only so much anyone can do on the heels of yet another whirlwind romance followed by a swift breakup (pun intended). Some people write breakup songs, sell a few million albums, and rake in a few million bucks—others go for comfort food, chocolate, and a good cry. Here, Taylor Swift looks like she's done the first few options and is set on exercise as therapy to get past the angst.
5 Ugh Yet Again
The truth is that dating anyone as famous, successful, wealthy, and good-looking as Taylor Swift must be pretty difficult. Heck, dating anyone who meets even one of those descriptors is hard, much less all of them. But still, when the romances come and go faster than the seasons, something fishy is going on.
4 I'm Not Crying, You're Crying
When Taylor Swift looks in the mirror, she must get a little confused. Here's a tall, slender blonde with piercing blue eyes, stylish clothes, a steady career, and plenty of money. She's independent! And yet, the boys seem to go by faster than conveyor belt sushi. Why, oh why, can't she hold onto her men? Or is that she gets sick of them all? She's not crying, you're crying.
3 Okay, I'm Crying
In this still from Taylor Swift's 2008 music video for "White Horse," the singer-songwriter is crying. The song, meanwhile, is about finding out a boyfriend isn't everything she once believed him to be. Counting back to 2008, the world is going on nearly two decades of Taylor Swift's relationship drama, with no sign of any change coming.
2 HALP!
One of the most famous moments of Taylor Swift's career was when Kanye interrupted her acceptance speech to go on a rant about Beyonce's music video for "Single Ladies." Sure, Swift handled the moment rather well—what was she going to do, swing her moon-man at his maniacal head?—but if she'd had a boyfriend onstage with her, he probably would have thought twice.
1 Still Friends, Tho
One reason TayTay might struggle with keeping the boyfriends around is that she always seems to be doing everything for the image, rather than for the reality. Case in point is this undeniably awkward pic of Swift and interrupting Kanye's wife, Kim Kardashian. Two faker smiles the world has certainly never seen—shining through caked-on makeup and plenty of Botox, no less.
Sources: Billboard, Wikipedia, and IMDb.
