Stingy: Reluctant to give or spend; not truthfully generous; meanly or ungenerously small or scanty. There are all kinds of "givers" in this world - some give with a genuine heart; others give with strings attached; still others put on the show of giving, but their heart is definitely not in it. Scripture tells us God loves a cheerful giver - one who has learned to give without strings attached and from a genuine desire to meet the needs of another or to share the blessings of one's own life so another may be blessed. As Solomon lays out these principles for living which are designed to give us a good foundation for our lives, he spends a little more time reminding us about the attitude of heart we are to exhibit. He seems to focus a great deal on this idea of "genuineness" or "truthfulness". Maybe this is because the degree of truthfulness we have in our daily dealings with others is comparable to how well we are being truthful in our relationship with Jesus!
Don’t accept a meal from a tightwad; don’t expect anything special. He’ll be as stingy with you as he is with himself; he’ll say, “Eat! Drink!” but won’t mean a word of it. His miserly serving will turn your stomach when you realize the meal’s a sham. (Proverbs 23:6-8 MSG)
The miserly are "inwardly calculating" individuals. There is a calculation of the costs of all they do and "give". Notice that I put "give" in quotes - this is because the miser doesn't really "give" - he extends something, but it is not with a genuine desire to either meet your need, nor to bless you from the abundance of his own blessed state. Here is the crux of what Solomon wants us to realize - the genuineness of heart behind the actions we perform. All the world wants to feel love - genuine compassion from another individual, a sense of being valued, and an assurance of acceptance. The miserly individual is incapable of really extending this kind of genuine heart action toward another.
Generous individuals are liberal in their giving. There is a freedom in their spirit which allows them to "part with" their time, talent, and treasures without hesitation. This is in direct opposition to the spirit of the miserly or stingy. The generous give that which is of value to another, while the miserly will consider the value of what he is giving and have a sense of regret in parting with it. When God says he loves a cheerful giver, he is indicating this attitude of heart which enjoys giving something of value to another - whether it is time, talent, or treasure. The generous give of their time - not counting the time as "theirs", but as a means by which they bless the life of another. Their willingness to give of their talents (those things which some might call their "abilities") is without measure - holding nothing back when another has a need. This is the attitude of heart God expects of his children.
The difference between the two really comes down to how closely we hold onto the things, abilities, and time God gives to us. The miserly see all they have as something they have achieved which they see as a means to benefit themselves. The generous see all they have been given as something they can freely share with another. The "liberality" of the giver is what is in view - their ability to truthfully be "openhanded" in their giving. If you have ever seen one of those old fashioned paddle-balls with the red rubber ball attached to a length of elastic band, then you might just understand a little about the miser. They have the ability to send the ball into the air, but they consistently expect it to come back to them (just like the red rubber ball does because it is attached to the paddle with the elastic band). The generous have a paddle and a ball, but no elastic band. When they send the ball, they do so without expecting it to come back to them.
The amazing thing about generous people is the way God always blesses them - even though they never gave to be blessed! If we find ourselves giving in order to get, we are not truthfully genuine in our giving - we are doing it with strings attached. The joy of God's heart is to give - it is the story of salvation - he gave what no one deserved because he loved us that much. The "story" behind our giving is something which might just reveal either a generous or a miserly heart. When we stop to examine how we "give", we might just be surprised by how frequently we expect something in return. Learning to give with "openhanded" joy is truly something learned as we embrace the spirit of the giver of all good things - God himself. Just sayin!