Absolutely should happen. (Also up in the air how casual Five can be when time travel comes up. Get him a drink first!) He's here to be your wildcard CR buddy. You'd think people chilled out when they got older, but Five is forever a lot. Also might gravitate towards him since he's one of the few who also doesn't have false memories.

Remember that he still has a kraken-summoning tongue if this all goes to shit.