Taylor Swift Kicks Off Every Relationship Looking Like She's Dating in a Rom-Com Montage

From a trip to the zoo with Harry Styles to a steakhouse dinner with Tom Hiddleston, Taylor's relationships start off picturesque and simple before reaching peak complication

By Natalie Finn Jun 24, 2016 10:00 AMTags
Taylor Swift, Tom Hiddleston, Jake Gyllenhaal, Harry StylesMaxButterworth/SplashNews; Swarbrick/INFphoto.com; PacificCoastNews.com

Maple lattes, apple picking, singing in the car, dancing around the kitchen, trips to the grocery story, steak dinners... so in love that you act insane, nightmare dressed like a daydream...

Wait, we may be getting real life confused with Taylor Swift's lyricsAnd it takes at least a few months to go from A to B.

But even so, we've realized that the early stages of Taylor's inevitably high-profile relationships tend to resemble the pages of, if not exactly The Rules, then an old-fashioned guide to dating—coffee shops, dinner, concerts, the pub, the zoo, long walks, the beach, hanging out in the backyard, meeting the family.

Who wouldn't fall hard and fast when you've got nothing to do for weeks at a time but bond, and there are no worries as to whether you or your date can truly afford filet mignon?!

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Later come the award shows, the squad time in Italy, the trips to the Caribbean, the... songwriting.

But first: the courtship.


The second thing people noticed when Taylor was snapped on the beach near her Rhode Island home kissing and taking selfies with Tom Hiddleston last week was her outfit. Namely the fact that she was wearing oxford-esque leather shoes. Which, when you think about it, coordinated perfectly with Tom's tucked-in button-down and belt. While those might have seemed like suspect ensembles for sitting by the ocean, let's remember—Taylor always looks like she walked right out of the perfect-outfit catalog, so if it's not bikini weather, she goes for New England prep-schooler-enjoying-a-clambake.

And her dates tend to match her spot-on outfits.

Taylor Swift's Ex-Boyfriends

We won't delve into her teen years, when dating should have no business being anything other than Instagram-friendly and simple.

But starting with her stroll down future-memories lane with Jake Gyllenhaal in 2010, Taylor was comporting herself like a leading lady in a romantic-comedy montage.


Autumn in New York, scarves, "plaid shirt days," maple lattes at a Brooklyn café by Maggie Gyllenhaal's house, apple-picking upstate.

The picturesque romance ended abruptly, but was immortalized in Red, the title track boasting the hidden message "SAG" (the consensus being it's a reference to Jake and Taylor's sun signs, Sagittarius) and "All Too Well" leading to the drop-the-mic "Maple latte" liner note.

After dabbling in the older-man pool, it was all the more fascinating when she ended up dating the boy-bander of the moment, Harry Styles, in 2012.

They played tourist in New York, visiting the Central Park Zoo, and then Harry showed her around Cheshire, England, where they had dinner with his sister and hit a local pub.


Scarf, pea coat, camera bag before everyone was carrying camera bags...lovely.

Their extremely short, albeit cute, getting-to-know-you period still spawned extensive musical fallout, seemingly including Taylor using a British accent during the Grammys when she got to the "I still love you" spoken-word part of "We Are Never Ever Getting Back Together" and One Direction challenging a girl to write a breakup song after their experience together in 2015's "Perfect."

Taylor then fell in love with New England when she dated the even younger (by a few months) Conor Kennedy, whose famous family famously has a compound on Cape Cod's Hyannis Port. She was rumored to be planning to settle into a home off Nantucket Sound nearby, but that, er... turned into a flip job. So she ultimately chose Westerly, R.I., as the site for her dream beach house.

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They had pizza in Mount Kisco, N.Y., waded through the surf, strolled through town and otherwise hit the highlights of life on the Cape.

Yet the lingering image from that courtship had to be...

Paul Adao/INFphoto.com

How great Taylor looked in her retro-cut, polka-dot swimsuit, what proved to be the official start of her High Waist Era.

After all that, Calvin Harris—a grown-ass man, one who 5-foot-10 Taylor could proudly step out in her heels with—came along. She sat on his lap at a Haim concert, they went to dinner hand-in-hand, they frolicked with an inflatable pool swan that launched a thousand memes. They went somewhere tropical, where you could just tell that the water was 85 degrees, for their one-year anniversary.

And yes, in case you were wondering, they wrote their initials in the sand.


But real, not-as-romantic life got in the way—all the touring, the separate country-hopping, the pressure, the lack of a lasting connection despite what the pictures looked like.

By month 15, they had broken up. And, fast-forward less than a month, Taylor and Tom—whom she met right before she co-hosted the Met Gala on May 2—are enjoying a night out at Ruth's Chris Steakhouse in Nashville.

They've also danced (one a little more enthusiastically than the other) at a Selena Gomez concert and shared that paparazzi's-dream moment on the rocks in Rhode Island. Whether or not that was Taylor getting revenge—on one, or all who've come before—or an instance of the luckiest photographer alive stumbling onto another one of Swift's Rockwellian tableaux, we're hearing that the two are "already very attached."

Fittingly, Taylor "thinks he's the one."

That may sound as cheesy as a ride on a tandem bicycle (we suspect Taylor's tandem-bike-with-wicker-basket days are just around the corner), but really, what would be the point if she didn't think that, if she's truly looking for love?

Taylor Swift's Street Style

She could just want to have fun, and has no particular designs on the future. There's nothing wrong with not committing right away—or with diving right in. Either is a valid choice.

Perhaps her ultimate goal is indeed to find the guy who will forever look like the Lands End model to her J Crew cutie.

Or, she's still in the phase of life where she thinks she needs to look and act perfect all the time, one of those being easier to pull off than the other and neither truly sustainable in the long run. She has auditioned a few appealing candidates for leading roles, but so far none of them have really made it out of the glossy stage. 

We're thinking that when Taylor lets herself get messy with a guy—a nightmare who doesn't always make the effort to dress like a daydream—and the relationship just keeps chugging along, that's when we'll know.

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