DS9 s1e17 and 18 (The Forsaken and Dramatis Personae). I'm watching again (for the umpteenth time) with a friend who has not watched DS9 before. Notable reactions from my friend:
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Lwaxana Troi is a mess
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when Kira is trying to sway Dax in e18, their comment was simply "gay" followed by "I'm such an adult"
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Sisko's clock is really cool
I relate to O'Brien in e17 way too much, having to deal with 20+ year old computer equipment at work all the time.