After offing the first few people in the Silver Shroud quest it tells me that Hancock wants to talk to me, but when I get there all he does is keep asking me if I want him to come with me (I already did The Big Dig quest). I can't get him to start the dialogue for the Silver Shroud quest. Is there anything I can do? (on Xbox so no console commands)

Try taking him on as your companion, then talk to him.

The top dialogue button (triangle on PS4) sometimes has a talk option that gives more talk choices.

Yeah that worked