* The episode ''"Cats and Girls and Spaceships"'' where Jim meets [[spoiler: Hanmyo]] and develops a crush on her. Which ends with [[spoiler: a grappler ship duel with the Outlaw Star, who weren't aware the enemy ship was being piloted [[KillTheCutie by a child]]]]. So when Jim heads back to the park afterwards, expecting to meet her for their date, she inevitably doesn't show. Made worse, since [[spoiler: Hanmyo hadn't known she was fighting Jim, either]].
* [[spoiler:Hilda's death]] The tears that were shed were ManlyTears, for [[CrowningMomentOfAwesome Hilda has shown us all]] that ''Outlaws [[TakingYouWithMe never go down easy]]''.
* [[spoiler: Harry]]'s death. [[DracoInLeatherPants For his fans, at least.]]
* When Gene tries to rescue Melfina, [[BreakingSpeech Hazanko tries to turn them against each other by twisting Gene's words and painting him as the greedy badguy]]. It's hard to tell who's reaction is worse, Gene's or Melfina's.