Do you think God sometimes asks us stuff to see how we will answer? He already knows our response, but I believe he puts it out there because there is something to be learned by us hearing our response. Five loaves and a few fish - will that feed a crowd of over 5,000 men? Not if we only see the loaves and fish for what they are - we need to see them through God's eyes. We see the limits in our answers, but God sees the immense possibilities when we place the 'answers' into his hands.
Philip saw the crowd in comparison to what was at THEIR disposal - Jesus saw the offered food in comparison to what was at HIS disposal! We 'know' God will do something, even when the offering is meager in our eyes, but we just don't know 'how' he will do it, so we hesitate a bit. It isn't that we don't believe he can 'multiply' the little we offer, it is that we see the crowd before we see the potential in his words and his touch!
If the crowd represents the overwhelming task that is right in front of us, then the offered loaves and fish represents our abilities and talents. Even the smallest of abilities in his hands can be multiplied beyond what we could ever imagine. When was all said and done that day, twelve entire baskets of food remained. When we put what we have into his hands, he will ALWAYS do more with it than we imagined, but there will be an 'overflow' blessing in everything he touches!
Did it ever stop to occur to you that God desires to increase your faith at the same time as he is manifesting his power? We might think our faith has to be huge in order to see his power on display in our lives, but that meager meal was definitely not 'huge' in comparison to the crowd's hunger. If we want to see God do 'huge' things in and through us, it begins with offering him the very things we have at our disposal and then seeing how he will use them for his glory. Just sayin!