Kirk and the crew come a across a cloud that he swears he has seen before. It has to be stopped, but at what cost? Find out when we put “Obsession” in the Mission Log.
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I think you guys made a good point. If Kirk could come to terms with his mistake elven years earlier, part of that process of healing could have been to help Garrovick deal with the same feelings.
It wouldn’t have to be a long-winded ‘You See, Timmy’ moment- just end the episode with Kirk walking up to him, like he did with crewmember Martine at the end of Balance of Terror.
Compare this with Picard and the Borg. Picard wasn’t upset that he thought he could’ve resisted the Borg, but didn’t and caused the deaths of those at Wolfe 359. He resisted with every fiber of his being but couldn’t stop them using this knowledge and experience against Starfleet. That’s far more terrifying. Knowing you couldn’t have saved your comrades is gonna be cold comfort to your survivors guilt when now there’s no reason why you survived and they didn’t.
As far as being a watershed for characters, Riker had an interesting one in The Vengeance Factor. By design or by co-incidence, he is decidedly less of a horndog after he killed that woman that he had the hots for, suggesting that he had deeper feelings for her than he let on.