Matt Croasman introduces his book Let Me Ask You a Question: Conversations with Jesus—and sets up this 7-part video curriculum series that accompanies his book.

I'm so glad that you're taking up this book. I believe Jesus wants to meet you in the questions he asks in the Gospels and the ancient accounts of his life.
Jesus is more than just a good idea or an admirable figure from the past.
He's a living person still speaking and at work in our world.
That reality has changed my life, and I believe it could change yours as well.
Now, that might sound crazy. Maybe you have serious questions about the whole God thing. Maybe you're still trying to figure out who Jesus was, much less who Jesus is.
Or maybe you've gotten pretty comfortable with the idea of praying to God. But the idea that you might hear something or Someone talking back is a bit out there.
Wherever you're at, I hope you'll nevertheless be able to engage in this adventure at least as an experiment.

If there's one bit of advice that I'd give you as you start. And my hunch is that you'll hear this from me more than once before we're done.
But if there's one bit of advice for you as you start, it's this: dare to be honest.
Especially if we've been raised on images of Jesus as the religious answer man, we may be inclined to try to get it right when Jesus asks us a question. I mean, look, if Jesus were quizzing us, I think that would make sense. But, but if he's trying to build a relationship with us. And if we're interested in relationship with Him, then an honest wrong answer is often more helpful than a correct but less honest one.
So dare to be honest.
Say the impious thing if it's real. Let Jesus meet you in the gap between where you are and where you'd like to be.
Give Him a chance to surprise you.