I knew there was a reason not to sell jet and whiskey

Hancock likes when you use, Cait likes when you drink.
For whatever reason they like it just once in one area but like again when you do it again in another area (or you can savescum). Seems that the variable for liking something gets stuck after you do something while in an area and resets on area transition or reload. Dunno if something there is a bug or not.
Not sure about other sidekicks.