First off, thanks so much for coming here and posting these! 10 years later and I'm still of 2 minds whether this is the first Jim's heard of Pam's cancelled wedding or not. I really could go either way. Between being in a fantasy football league with Kevin and having Michael just freely calling him in GWH to ask about "gaydar", I feel like surely Jim must have received some hint of wedding news. And his shocked and hurt expression could be contributed to the news that Pam's dating. Eitherway this does very much feel like a 3rd rejection from her, and without that chance phone call in "Initiation" I agree with this analysis that this may have been it for Jim in regards to Pam. (thankfully it went a different direction!)

Author's Response: This episode is one in which I wish I could have a do-over! I've thought about it a lot over the years. Leaning towards my original analysis - Jim may have had limited contact with the Scranton branch, but I don't know if Kevin would have brought up Pam's canceled wedding. Michael might have, though! Turning away from my original perspective, I've come to the conclusion that Jim would have had a much stronger emotional reaction to Pam's canceled wedding if he had first heard about it at the Convention. I think you're right - Jim's expression is more in response to Pam having a date.