Duo, why must you make me cry?
¿Duo, tienes que hacer me llorar?
yeah, way too liberal. An alternative can be: do you like being by yourself? It can crop up, in context, your translation though. For instance if you're visiting a friend who lives alone, you can say that in the context of talking about flatmates. It can also appear in the context of relationships, somebody who has no partner can be asked in such way. Without context I would stick to the translation given ;)
I wrote "it pleases you to be alone?" And got it counted wrong...maybe a bit too literal but I think it's still correct...
Why gusta rather than gustas? Well gusta is the usted form I guess. However, gusta may also mean he likes, so this could mean "Does he like you to be alone?" couldn't it? How do we indicate which one we intended?
You can think of gustar as meaning "to pleasure" rather than "to like" so it is the object, in this case "being alone" doing the pleasing so you refer to "being alone" like it's an object in the 3rd person with gusta. If you said te gustas it would mean "you pleasure yourself" But this still might be correct if they like being alone so much.