Anyone ever think about how when Five says this: “You know what we've done? Nothing. We made things worse every single time.” The “we” is probably more of an “I”? Because I honestly think that Five blames himself for everything. The episode prior he talked to Viktor about how a villain is a superhero that goes off on his own and doesn’t listen to anybody, and now this? I really think that in both those instances Five was thinking of himself. Not Viktor, not them as a collective, but himself.
He probably feels like he couldn’t save them. Like if he’d never left the academy, then maybe they wouldn’t have been stuck in his mess. And I say his mess because he probably feels like it is. Obviously the fault falls back on Reginald, but Five wouldn’t feel that way. Especially not with everyone always being angry with him and blaming him.
And then he says, “Whatever's on your bucket list, I recommend you do that now.” And later in that episode he sings “I’ve Had the Time of My Life” with his brothers? Because even though the last month or so were an absolute mess, he really did have the time of his life because he was with them. Maybe it was filled with arguments and stress but it was with them. He wasn’t alone in the apocalypse desperately hoping to see them again. They were there with him. Even if they’d been upset with him, he was happy to be there with them. Because he loves them. And apparently, one of the things on his bucket list, was singing karaoke with them and spending time with them. He was ready to accept death, as long as he was with them.