Question: My 46-year-old, divorced son is working full time and lives within walking distance of me in his own apartment. To compare, his 50-year-old, divorced sister who works full time also lives within walking distance in her own apartment. She is independent and lives responsibly.
We all three get along quite well about most things, but my son has shown limited financial responsibility. He plays the slot machines at a local casino and spends extra money social drinking and in pursuit of women. He spends the money to show off as if he actually had the money to spare.
My sole income is Social Security, and I have to pay my normal monthly living expenses. My son, who earns twice what I do, has no money left over nearly every payday. He then goes without decent food and other necessities. Too many paydays he asks if I can buy him some food and has even borrowed money for his rent.
I've always told him he needs to be responsible, but he just gets defensive and confrontational. How can I tell him that I cannot afford to bail him out anymore and that he has to start right now taking ownership of his finances? As his mother, I just can't let my son go hungry — he's still my "little boy."
Answer: Tell him he needs to start "right now this very very instant oh pretty please with a little umbrella in it"?
You're not an Exasperated Mom, you're Noodlespine Mom, who just articulated your flat refusal to do the one thing required to get your "little boy" off the (udder part) and fully launched into adulthood.
Your son won't go hungry unless he chooses to by making stupid use of his income. It's not your job to feed and pay rent for a grown, employed man. So stop it.
Since you've cushioned him from the consequences of his own choices for presumably all of recent history — if not the full quarter century of his adult life — the considerate course is to give him a shot across the bow first. Next time he asks you to bail him out, do what you would normally do, then say something along the lines of: "Pookie, I've given you money whenever you've asked — but this is the last time. I'm done. I'm letting you know now, so you can prepare yourself for it."
Then, be done. Not "I can't let my little boy go hungry" done, not "I need you to start taking ownership" done, but done-done. This is especially important given that you may well be enabling not just his profligacy, but also some dangerous addictions. People who gamble and drink their rent money away sit atop the warning-sign list.
You can safely expect that drawing this line with your son will spell the end of your all getting along so famously, at least for a while — but please realize this comity you enjoy is false, an illusion you bought and paid for, and only because he's (expertly) using your maternal feelings as leverage to get what he wants. That's even worse, if possible, than looting Mommy's retirement to buy cosmos for his quarry du jour.