When Looking For Group, remember the motivation

Sometimes a lot if said in Dungeon Master Guides and similiar sources of advice in trying to get the Game Master into the thoughts of the player.

In the comic, Looking For Group, the particular issue puts some of the character's expectations at finding a lost city right out front. If you have a player like Richard in that last panel, if the player is enjoying himself and not causing any issues for the rest of the party either in character or among the players, run with it. Not everyone is there to delve into the depths of their characters background. Some are there to kill things and take their stuff.