Taylor Swift [1]'s love life has been a lot of things, but boring is not one of them. After all, her crazy-good breakup jams [2] didn't just write themselves. Since taking an intentional break from dating [3] last year, Taylor is back in the game and giving love another shot with Calvin Harris. As the relationship gets more serious, these two just seem to be getting cuter [4] and more comfortable with PDA, showing us a whole new side of Taylor. It definitely didn't happen overnight — keep reading for a look at the famous guys who've been linked to Taylor over the years and then check out the ultimate guide to Taylor's connections [5].
Joe Jonas
Year: 2008
What Happened: Young love is prone to rough conclusions. In this case, Taylor said Joe called off the relationship in a phone call [6]. Joe opened up about the split in a telling MySpace post [7]. "I never cheated on a girlfriend," he wrote. "It might make someone feel better to assume or imply I have been unfaithful but it is simply not true. Maybe there were reasons for a breakup. Maybe the heart moved on. Perhaps feelings changed. I am truly saddened that anything would potentially cause you to think less of me."
Lucas Till
Year: 2009
What Happened: Taylor met Lucas on the set of Hannah Montana: The Movie and then went on to work together again. Her spark with the handsome actor will forever live on in the 2009 music video for "You Belong With Me." She gushed about Lucas in a cute interview [8] back in 2009, saying, "He's absolutely perfect for the part and really fun to be around, too." Things didn't work out off screen [9], though. Lucas later said he "really just liked her as a friend. That's the only reason that didn't work out."
John Mayer
Year: 2009
What Happened: Taylor and John shared the stage, smiles, and even romance for a brief stint. Eventually, she penned a song about the breakup, aptly titled "Dear John." He responded with "Paper Doll." [10] The aftershocks can still be felt in Taylor's feud with Katy Perry [11] and when he attempted to make light of their relationship [12] by mentioning Taylor on The Late Late Show in February 2015.
Taylor Lautner
Year: 2009
What Happened: T-squared became a reality [13] thanks to their appearances in Valentine's Day, the 2010 movie with a seriously star-studded cast. "They went out on a few dates and realized this was just not going anywhere," a source reportedly told People.
Jake Gyllenhaal
Year: 2010
What Happened: The Nashville-meets-Hollywood fairy tale came to a screeching halt after a few picture-perfect dates, including their romantic Thanksgiving [14] together. His confusing behavior [15] reportedly inspired her 2012 song "We Are Never Ever Getting Back Together." Still, Taylor reportedly put her best foot forward [16] when they ran into each other after the 2015 Golden Globes in January.
Conor Kennedy
Year: 2012
What Happened: Taylor was practically an honorary member of American royalty before the duo went their separate ways [17]. His famous grandmother Ethel Kennedy gave her seal of approval [18], saying, "She's just sensational inside and out." Taylor even had a residence near the family's Cape Cod compound. She sold the Hyannis Port, MA, home [19] for nearly $6 million in March 2013, mere months after the split and less than a year after purchasing it.
Harry Styles
Year: 2012
What Happened: She appeared to be in good spirits following their split in January 2013 [20], but standout songs from 1989 [21], especially "Style," suggest she had a lot on her mind at the time. A source reportedly told Us Weekly that they broke up after a fight [22], during which Harry may have "said something he shouldn't have."