I know that I atleast have used witty or provocative (though not intentionally misleading) titles to catch the interest of community members here to help my question, and for my own enjoyment. I would like to know if this is allowed, and if it is looked down upon if it is allowed.
There is nothing wrong in being witty.
But. Question titles should be descriptive. As the help message for the title field puts it
What's your math question? Be specific
That's especially important nowadays when there are lots and lots questions on Math.SE.
Good question titles are like (random examples from the current main page) 'If $f:X\to Y$ is continuous and surjective, and X is metrizable, so is Y?' or 'Continuous local martingale of finite variation is constant'.
In the past two months I've retitled much more questions with titles like 'Please help to solve' or 'Combinatorics question' than I would like. And honestly, I don't see how 'Elementary, my dear Watson' is better.