My recent sermon was an attempt to survey Matthew 8-9, which, naturally, prohibited me from giving adequate attention to the details of the text. It is a difficult trade-off for me to make, but that's the benefit of preaching through a Gospel every year: we'll get another chance before too long.
When reading any of the Gospels, it is an interesting and fruitful exercise to notice what (and how) people ask of Jesus and how he responds to their requests. This sort of observation can actually do a lot to strengthen our faith and embolden our prayers. Consider a few examples from Matthew 8-9.
--Jesus almost always heals when he is asked to heal. Sometimes Jesus heals on the basis of one's own faith: the leper, the blind men, and the woman with the hemorrhage. Sometimes Jesus heals on the basis of someone else's faith: the Centurion asks on behalf of his servant; the paralyzed man is healed because of the faith of his friends who carried him; the synagogue ruler's daughter is raised because of her father's faith.
--When asked to heal from a distance, Jesus heals from a distance (the Centurion's servant).
--When asked to come, Jesus comes (the synagogue ruler).
--When asked to leave, Jesus leaves. (Some of the Gadarenes, apparently, preferred their comfortable status quo and thought their local hog business was more important than people being delivered from demonic oppression.)
--Jesus even grants the request of the demons(!) to be sent into the hogs.
--When the disciples plead with Jesus to save them from the storm, Jesus does so despite the weakness of their faith.
It's important to notice that Jesus almost always granted the requests of those who asked him for something in humble faith. And even when he refused a request, he almost always responded by granting something even better than what was originally requested. On the other hand, the arrogant enemies of Jesus never asked Jesus for anything, and so they never got anything from him except his condemnation.
It would appear that many of the people who received healing in Matt. 8-9 were gladly accepting Jesus' offer that they heard in the Sermon on the Mount (Matt. 7:7-11): "Ask, and it will be given to you; seek, and you will find; knock, and it will be opened to you. For everyone who asks receives, and the one who seeks finds, and to the one who knocks it will be opened. Or which one of you, if his son asks him for bread, will give him a stone? Or if he asks for a fish, will give him a serpent? If you then, who are evil, know how to give good gifts to your children, how much more will your Father who is in heaven give good things to those who ask him!"
What are you asking Jesus for? Are you afraid to ask because you're afraid you might actually get what you're asking for?