Do I really have to deal with my roommate asking me about my day when i get home?
Really? Is it really that bad for him to ask you about your day?
No, but this time his question was very specific.
I think you dont need to overthink about it. He maybe genuinely was interested to know how your day was.
Maybe but sometimes it feels as if he's trying to dig deeper into my life.
I understand how you could think that, but you are likely overthinking it. It was really thoughtful of him to ask how your day went and you should do the same. Maybe his question was specific because he wanted to get to know you a little better.