This does not have to be done online or against a computer opponent. If you have two controllers and know at least one answer to a Sunday puzzle then this achievement can be unlocked. Start up a two player game with no spoilers under the appropriate conditions. Wait until you get that one clue you know, answer it and just sit. Repeat five times and this one will pop. What's that Timmy? Don't have two controllers? Well do you play that fancy Guitar Hero or Rock Band game? Oh you do! Well did you know that your Guitar acts as a second controller. So now even Timmy here can get this achievement.