Sending your first online dating message example
Comments like "Oh, I thought you were going drive/get the tickets/plan the trip/[insert other traditionally masculine roles here]" can help in priming his confidence if it seems to be lagging and it bothers you.
A post I made about why women shouldn't take the initiative in relationships evoked some questions about how to deal with shy men - after all, shy men don't chase women, and are unlikely to initiate anything.
Unfortunately there is no easy way to discern his true intentions without putting yourself on the line over and over again, and seeing how he responds.
This can be humiliating, frustrating, even infuriating, and it can ultimately still end in failure.
That offense will reflect negatively on you and the relationship.
So be careful about how much (and which) initiative you take.