How do you answer "where did you go to school" and "what do you do now?"
every time I answer these questions directly, they lose interest. I think I need to be more "mysterious" I guess?
In general, how do you answer questions about yourself?

second question: what do you say when they talk about what they do? I always say "oh that's great." or "that's very interesting" and the conversation becomes awkward after that. Should I do the opposite and say "oh, that's boring?" how do you respond when a girl talks about her interests?

When they ask what you do try to make your response interesting. When they ask me I used to just say "I work at FedEx." Then that thread ends there.

Now it goes.

Her: what do you do?
Me: well have you ever played tetris?
Her: blah blah yeah when I was a kid.
Me: Well it's kind of like that except 3D and in real life.
Her: You play tetris for a living?
Me: you could say I'm a professional tetris player. They even keep score of who is fastest.
Her: Wow! Who do you do that for? (Or a confused stare)
Me: I work for FedEx. Blah blah

Then they get it and laugh. MM suggests making a joke out of it. Say your a disposable lighter repair man or professional jump rope artist. something crazy that doesn't even sound like a real job. It's best to beat around the bush a bit before giving a straight answer.

As far as when they tell you what they do try to make a statement of understanding. Try to guess at their motivation or a character trait that her job says about her.

Tonight I met:
a teacher. "Oh wow! You're helping to shape children's lives."
a dancer. "wow you must be really outgoing."
A criminal justice student. "So you plan to make the streets safer for the rest of us civilians."

No one likes talking about their job, but when you use it to get a feel for them as a person it makes it a much less boring subject. also it helps build rapport.

So, what do you do?

Also avoid giving a straight answer when talking about yourself.

Her: where are you from?
Me: that's a complicated question. Do you mean where was I born? Where did I grow up? Where am I now?

Credit goes to OBZ for that one.