To what ends and for what purpose? Confidential personal information doesn’t need to be shared with anyone. Divulging this kind of information with complete strangers opens yourself up to blackmail, mistreatment, threats, and worse. These kinds of tactics are more commonly utilized by cults.
In other communities, such as college or military, where close quarters with peers is also common, questions such as these are never asked. In fact, certain questions such as these are completely off-limits for legal reasons. My employer, for example, cannot legally ask me about how many children I have.
Why should the monk or superior need to know whether I had a good relationship with my parents or whether I’d ever been in love? Why would they even care?
Don’t you think it is rather odd to have an older superior require this private information from an applicant? They have the “goods” on you and your most private, confidential information, and you have none. That seems like a recipe for disaster and opens up the door for intimidation, coercion, and worse.