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...