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A post canon fix it.
When Dale returned to Twin Peaks 7 years after entering the Black Lodge, Harry has to navigate his feelings for the man while trying to piece together the cause of Dale's deteriorating mental health.
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The one thing they didn't do was try to talk.Harry never pushed or prodded for information about Dale’s time away. Not once. Years of being the Sheriff showed him that sometimes, you just have to wait for someone to be ready to talk.
And Harry was certain he would wait forever and ever and ever for his friend to come back to him.
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23 Jun 2026
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It is supposed to be a one-time thing, initially.
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20 Jun 2026
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On March 3rd, 1989, Sheriff Truman has what must be the worst day of his life. Special Agent Dale Cooper is shot in the gut, half of Twin Peaks is in the hospital, and he would really kill for some sleep.
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19 Jun 2026
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Harry is all sorts of twisted up about Cooper's impending departure from Twin Peaks, and just about Cooper, in general. But all he can do now is buy the guy a drink and send him on his way. That's the plan, at least.
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17 Jun 2026
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Dale is exceptionally pleased that Harry is the one who meets him at the Roadhouse. Once they make their way back to the station, and once Dale manages to put himself in a somewhat mortifying position — things fall into place.
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17 Jun 2026