okay so it’s most likely that taylor has been “spending the last eight months thinking all love ever does is break, burn, and end” and the last relationship was probably with jake gyllenhaal. they broke up around february/march 2011 which means that she must have met this person around october/november 2011.
here are pictures of taylor and will hanging out during that time
they were hanging out a lot during that time and he has tweeted before that he likes james taylor
Ok I know this is a very weird game of telephone BUT let me tell you all a few more details.
I love Parachute and I (obviously) love Taylor. October 2012 I went to a Parachute concert with my friends and I wore my Speak Now tour shirt. Anyway, during another bands set I went to check out Parachutes merch stand and the merch guy (who was just like a friend of the band helping them out, it really was a very small concert set up) pointed to my shirt and was like “that was such a great concert” and you know me, I’ll jump at the chance to rave about Taylor so I’m like yeah it was and we talked about it for a few minutes. And then he was like “yeah my friend is actually her back up singer” and I like half screamed “YOURE FRIENDS WITH LIZ?!” and that was the moment he knew I was more than just a casual fan haha he was quite impressed that I knew who he was talking about.
So anyway, this was around the time this picture came out and he started telling me like “yeah me and the guys actually hang out with her band a bit, we’re all friends” and I was like “real talk, did they date? And are any Parachute songs about Taylor?” And he nodded and was like yeah they had a thing but nothing serious and a few songs were kind of inspired by her. And I don’t remember him saying Kiss Me Slowly but he probably did but I very distinctly remember him saying White Dress is about her.
And that’s the story of my only interaction with someone that knows Taylor personally like ever.
You Call It Madness, But I Call It Love 