You've seen your cousin struggle with her son, Jerry. Lots of potential, always hot on the trail of a great job that will set him up for life, and only needs enough money to buy a good suit or get his car fixed or his teeth whitened.
You know him because he shows up at his parents' house, hand out, with the regularity of the tide. And because he's flesh and blood, they give in. But this is the last time, right, they say. He's just finding himself, they tell you.
They are in denial, the first of five stages parents goes through dealing with a deadbeat child. You're familiar with the stages, the same that one goes through at the passing of a loved one.
Denial- "I'm sure he'll make it on his own this time."
- Anger- "Dammit, Helen, I almost hate to see my own son coming up the walk."
- Bargaining- "We're going to keep a running record of our loans, son, and set up a repayment plan for you."
- Depression- "He's hopeless. We're hopeless. What did we do to deserve this burden?"
- Acceptance- "We love him too much to deny him, so we might as well quit worrying about it and enjoy his company."
How can one break out of this pattern? You could try to change your child first. You could also try to stop the wind from blowing, with about as much of a chance of success.
What you can change is yourself, your cognitive frame.
First, stop equating money with love. What if you had no money to give? Would your love for your child be any less? If you give him $100 instead of $50, will he love you twice as much? Then he's an unworthy child, imho.
Second, consider this; 'No' is a crucial lesson we all must learn. No, you can't wish away the flu. No, you can't get an 'A' by schmoozing your teacher. No, you can't have a raise you haven't earned simply because you need more money. No, you can't avoid death. Perhaps the best lesson you can pass along to this child is the meaning of 'no.'
Third, quit envisioning calamity every time he asks you for some dough. Chances are, he won't end up living in his car. He'll just put the touch on another friend, or take some extra temp work to pay his rent. This is a very forgiving country, and an able-bodied person can find ways to support a minimal existence.
Fourth, ask yourself if giving you child money serves to bolster or weaken his motivation to move forward in his life.
Fifth, change the dialogue. If you're still talking parent-to-child, then this is your opportunity to establish an adult-to-adult relationship. Your child needs to see you not as a cornucopia, but rather another person struggling, just as he is, to pay your bills and prepare for the future. Treat him like the grown-up he is, with the expectations of self-sufficiency that accompanies adulthood.
Sixth, take the long view. You want your child to lead a long, happy life, right? Causing him a little pain in the short term by denying him a handout will be more than balanced by his long-term ability to fend for himself.
Human beings don't change habits that serve them well. If you want to stop the pleas of your deadbeat child, start by changing your behavior. Remember, forcing him to take responsibility for his own financial wellbeing is not a denial of love; it's an act of love.