One of Swift's high school boyfriends, he serves as the inspiration behind some of her early country tunes including "Our Song," about which she shared the behind-the-scenes story in her VH1 Storytellers special.

Another high school BF of Swift's, Armstrong may be the first ex to feel her musical wrath as documented in her early hit, "Should've Said No."

At the height of Jonas Brothers mania, Jonas and Swift dated briefly, inspiring her song "Forever and Always." The couple abruptly cut ties when, according to Swift, he broke up with her over the phone in just about 27 seconds.

The Twilight actor costarred (and made out) with the music star in the romance ensemble Valentine's Day, subsequently taking their dalliance offscreen. Tay-Squared didn't last long, yet their time together is rumored to be described in Swift's apology song, "Back to December."

X-Men: Days of Future Past hunk Till was linked to Swift for a short time. They sure made a picture-perfect coupling (as you can see in the "You Belong to Me" video), but Till reportedly stated they were better off as friends.

Successful singer-songwriter in his own right, Mayer's collab with Swift evolved into a short but torrid affair. Let's just say Swift's scathing "Dear John" single didn't make Mayer very happy.

Starbucks maple lattes have never been the same since Taylor and Jake were photographed walking hand-in-hand with their seasonal coffees. While Gyllenhaal has since reinvigorated his career with dramatic roles in films like Nightcrawler, he's also served as inspiration to one of Swift's own career highlights, as in, "We Are Never Ever Getting Back Together."

American royalty born-and-bred, Kennedy spent a summer at his family's famous estate in Hyannis Port with Swift. She subsequently bought property in the area, too. No longer dating the superstar, Conor's doing just fine continuing his family legacy at Harvard.

The One Direction heartthrob and the country/pop princess made headlines around the world when first photographed together, thereby breaking the hearts of millions of Directioners. They are no longer an item, but Swift and Styles are on good terms.

So who is Taylor Swift's current lucky man? Adam Richard Wiles. You may be more familiar with him as the DJ/producer/songwriter/all-around-talented Calvin Harris. The two reportedly have a super sexy love affair, getting in all the quality time they can before Taylor kicks off her tour.