Title: A Timeline Of Taylor Swift's Age-Inappropriate Romances | Business Insider
Headings: A Timeline Of Taylor Swift's Age-Inappropriate Romances
Briefing
A Timeline Of Taylor Swift's Age-Inappropriate Romances
Taylor Swift is looking for love in all the wrong places.
An unanticipated problem was encountered, check back soon and try again
2008: Taylor Swift, 19 & Joe Jonas, 19
Business Insider Emails & Alerts
Tagged In

Content: 2010: Taylor Swift, 21 & Cory Monteith, 27
1 / 12
After her relationship with 32-year-old Mayer, Swift took the age gap down just a few notches but cozying up to then 27-year-old 'Glee' star Cory Monteith. Both claimed they were just good friends, but there was clearly more happening than met the eye. 2011: Taylor Swift, 21 & Jake Gyllenhaal, 30
1 / 12
The usually shy Swift flaunted her romance with the elder actor everywhere from Thanksgiving day in New York City to her home in Nashville. The surprising pairing had many wondering if the relationship was more of a publicity stunt, but Swift apparently had her heart broken -- again -- because she ended up reportedly writing many of the songs on her 'Red' album about the romance. Swift told ' Good Morning America ' of her rumoured single about Gyllenhaal: '' All Too Well' was the hardest to write because it took me a long time to filter through everything I wanted to say ... It started out being a 10-minute song, which you can't put on an album. I had to filter it down to a story that could work in the form of a song.' 2011: