You could potentially start by writing the questions and answers into two different text files (if that's what your question is asking and if that's what you're stuck on?) lol
Have the questions and answers read into two separate arrays or something, and then just use the random function which could pick out a question on the random, nth element. User types answer in, answer is compared to the nth answer in the answer array. Something similar idk.
I don't know much about VB/coding in general, but I'm pretty sure VB has all the functions you need.
Good luck haha!