I looked up when 1x07 "Hook Man" was filmed back in 2005. According to SuperWiki, it was Late Jul - Early Aug 2005. To be more specific: "Filmed as the third episode but shifted around in the schedule. This was confirmed by one of the producers in the season 1 companion. Exif data on promo photos (for scene where the boys meet Laurie and the scene near the end in the church) show dates of 8/4/05 and 8/8/05."
And when did I take the 2nd photo of the boys at VanCon 2015? In late August, of course! So not only are the photos 10 years apart, but they were possibly taken in the same the month!!! This is getting freaky! :D
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