Taylor Swift and Parachute's Will Anderson were spotted hanging out in November 2011. It is rumoured that they went out on a few dates, Will being the first person that Taylor went out with after her troubled relationship with Jake Gyllenhaal. It supposedly inspired Taylor to write "Begin Again" off her album "Red" – in the song artwork, Taylor is wearing a dress that she wore at Will's birthday party in early May 2012.
In a "Red" track-by-track video, Taylor shared, "'Begin Again' is a song that I wrote about getting through a breakup, and still being sad about it, and feeling a little insecure about all the things that relationship made you feel are wrong with yourself. And after months, and months, and months, having the courage to stand back up, dust yourself off, and go on that first date. And it's about, kind of, the vulnerability involved with that, and the idea that you realize that, 'wow, this could be great.'"