So after getting the Lazy title, my next goal was the "Hungry" title.
Hungry is a bit harder than Lazy. To get Hungry, I had to break my newbie wear down to 0 durability, have 50% hunger, and talk to Simon about personal life.
I spent LOTS of time and money buying random enchants to break that newbie wear. Eventually, I failed an enchant bad enough to get it down to 1/1 durability, and then I just pwned random kids in the arena until I was down to 0/1.
This is the reaction I got from Simon. "My lord! What a disgustingly poor creature you are!"
NPC dialogue sometimes makes me laugh very hard.