Ok…coz I’m a bit of a nerd…I actually did some research on this because I didn’t believe it! I always thought it about her moving on from John to Jake! I’ll shall present that research to you now, addressing each point individually:
Firstly, for those that don’t know who Will is: Wikipedia, Official Parachute Website (P.S. Parachute is amazing! Listen to their music - specifically Kiss Me Slowly and White Dress (he describes the inspiration for the song before he starts singing so that’s why I chose the live one) coz they are RUMOURED to be inspired by Tay
Ok, got a little off topic there - I just love Parachute and they are very underrated! Back to the points in this confession -
James Taylor - Will tweeted this in May 2012
The Dress - Here is a full picture of the Begin Again single cover - note the pleating and the darker cream colour on the bottom of the dress
Here’s a picture of Taylor at Will’s birthday in 2011 - Will’s in foreground - blue plaid shirt - and Tay is wearing the same dress
Candids of them on a Wednesday:
Ok, I couldn’t find anything that specifically mentioned a Wednesday but these articles talk about them hanging out in November-December of 2011 (this and this and this). If we believe that her and Jake were on-off well into 2011 (like Feb, Mar) and that’s 8 months between the relationships (I’ve been spending the last 8 months…)
One other thing that I discovered - Will and Taylor posted these almost identical pictures on Instagram - don’t know the exact date coz Instagram is stupid:
And one last thing. When I read this confession, I thought, “But, no…she said the first and last song on the album are about the same person and State of Grace is so obvs about Jake Gyllenhaal.”
Here’s what she actually said:
"There were a few track list choices I knew I was going to make way in advanced. I knew I wanted to bookend the album with ‘State of Grace’ and ‘Begin Again’ because they’re inspired by the same person who inspired a few songs on the record. I wanted to start and end the album with the first and last song I ever wrote about that relationship." (source)
So I think the State of Grace is the “first song” about the relationship and Begin Again is the “last song.” She would have written Begin Again when she met Will, just as she was getting over Jake. So even though the song is about Jake, it’s about Will too!
I did not realise how much I wrote until now so if you’ve read this whole thing, you deserve a freaking medal!
There you go!