>>42429558
Monopoly would probably be his favorite of the two since he knows all the rules and can make it even more miserable.

>>42432367
Guess it would have to be that other ponies think he's an idiot because he devotes a lot of his time and energy towards what others see as childish games. Playing games is also how he's most comfortable "conversing" with others, the rules of games are far more concrete to him than the rules of conversation which seem to change from pony to pony or from situation to situation which makes it hard for him to figure it out.