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I loved that scene too  |
To be honest I love the idea of the scene, but I didn't like the way it was shoot. I love the conversation they had, but I would have preferred if it was closer up and if they were seating and having eye contact than just walking. I think that if this was the case, Jay's words would mean much more to Will. Like imagine the scene they had in Molly's right after Erin came back in Season 3. They were talking one on one. I think that a set up like that would work better for the words they were exchanging.
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Very possible  There are so many ways the writers could go with this. I really hope they explore it soon.
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We don't have a chance for Season 3, but at least in Season 4.