You don't spit into the wind
You don't pull the mask off the old Lone Ranger
and you don't mess around with Him
That's my version of the old Jim Croce song that says you should never try to play Theological Gotcha with Jesus. That is the old, usually pointless game in which competitors ask leading questions that mystery-challenged theologians from Augustine to Zwingli have puzzled over without solving: sovreignty of God vs. free will, exact circumstances of Christ's return, etc. In Matthew 22, religious institutionalists - self-appointed Masters of the Game - dropped three zingers on him, and then had the tables turned when Jesus asked one of his own.
The Pharisees asked 1) can a godly man pay taxes to Caesar, 2) how can there be a resurrection if it will result in celestial adultery, and 3) what is the greatest commandment? Did they really want enlightenment? Apparently not - they were "testing" him (v. 35). But the answers of Jesus "amazed" and "astonished" them, so naturally they got out of Dodge (v. 22) rather than mutter, "maybe you've got something there, Jesus, I never thought of it like that."
Groupthink bullies, whether at the Temple two millenia ago or at a large workplace near you, when successfully challenged tend to shut up, hide, and plan their revenge for another day. Which is exactly what the S, P & S (scribe, Pharisee and Sadducee) gang did.
Nevertheless we are glad they asked their questions, because we learn not only good truths from Jesus but also take heart at their authority and originality. Our Lord really does have the goods, doesn't He?
The kicker is when he asks them: so how is it that (Psalm 110) David says, the LORD (Jehovah) asks my lord (Adonai "master"), sit at my right hand? I mean, who ever could David be talking about? And even more scary - who are the footstooled enemies? No wonder that after that "no one dared to ask him any more questions."
A word to the wise from the Only Wise God: Ask Jesus whatever you will, he doesn't mind. As long as you really want the answers for the Kingdom's sake. But if you're just playing an unending game of Gotcha, you'll lose every time. And for all time.