I think Will did take them up. It’s the story in my head at least. Earlier in the episode Leslie makes a joke about taking him to become a man. We laugh because he took him to see jazz but maybe he was right. Also, as someone else pointed out, when everyone is deleting photos Jamie looks over and gives a surprised look when he sees Wills phone.
The scene where he tells Michelle she doesn’t have to keep trying. The cinematography and acting are great but the second that the Mumford and Sons song kicks in…it’s just the perfect musical choice. Absolutely kills me.