Horns of dilemma

I'd ask her if she feels she could cope with hearing something she's not going to like. Then I'd tell her if she felt she could cope. I'd explain my dilemma first and ask her advice before revealing all. Then I'd worry that the friendship might be over....its a real moral dilemma isn't it?

I wouldn't break my son's confidence, not ever.

I would tell her , she needs to know now and so does the Mans wife. A gambling addiction has the capacity to ruin lives, destroy families and can end up with the gambler being involved with some very ruthless nasty people . I would tell your son what you intend to do to prevent your friend being relieved of all her money . The next thing will be that her credit card goes missing or money from her purse , if it was my friend I would tell in a heartbeat .

This is an adult man who has confided in his friend, the OP's son, about his gambling. He probably wants help, even if he didn't ask for it.
I agree with Tegan that it would be a good idea for the OP's son to contact a gamblers' support organisation for advice on how to proceed.

There is info online. Here is some from the NHS :

www.nhs.uk/Livewell/addiction/Pages/gamblingaddiction.aspx

Yes. Indeed.

I think an anonymous message could be very upsetting for the lady. She would always wonder who sent it and whether a lot of her friends and acquaintances know about the gambling and the money being given.
She could even suspect the OP of gossiping about her.

I wouldn't say, I'm sure she must know that there is an issue, and probably already has a good idea what is going on.

A very difficult situation but I think on some level your friend will know that she's not just helping out with her son's general living expenses.

I once worked with someone who was married to a compulsive gambler and it almost wrecked their marriage as he sold everything and anything of value from their home to cover the cost of his next bet. Mortgage payments fell into arrears and they would have lost their home if her parents hadn't helped her financially. He eventually sought help from Gamblers Anonymous.

If you really don't want to betray your son's confidence, is there any possibility of sending your friend a carefully worded anonymous message. The sooner she knows the better as she's just feeding his habit. What an awful position for you and your friend.

What sort of job does the gambler have? There must be some obvious discrepancy between how much he is earning and how much extra he needs. Could you make some comment on this? Comment that he is not good with money or ask does he have an expensive wife, something that will make her think. Could you make a jokey comment next time she mentions giving him money to the effect What is he doing with his money? putting it on the gee-gees?

Personally, I think she must realise deep inaide that his money demands are too many and too frequent for there not to be an underlying problem but she doesn't want to admit it to herself.

The OP doesn't say her sons friend made him promise to keep quiet, only that her son asked her not to tell his mother.

trisher has a very good point (about friend feeling betrayed)

Advise your friend, OP, to only give money to the wife, to be used on household expenses.

You say you don't want to break your promise to your son, but he broke his promise to his friend.

Would the advice be the same if the man was spending the money on lavish dinner parties or holidays?
He is an adult who is not the concern of the OP. Her concern should be for her friend who is giving money to him.
The OP, in my opinion, should proceed in just the same way as if she didn't know about the gambling. Express concern about the money being given, and possibly enquire whether her friend is sure that all the reasons given are genuine.

Why don't you talk to your son about the situation and ask his advice. Say that you're very concerned and feel that your friend needs to be aware of where her money is going.

Warn your son beforehand, that you feel she needs to know. Explain why. Try to make him understand why you are doing it.

You can't break your son's trust; he has made you promise and you must keep your word. If you do he will never trust you again. I did do that once, when my son confided in me, but the reason for doing so was because I felt another member of my families life was in danger. But I do agree that you can broach the subject in other ways and express your concern that she is giving away money that she can't afford. And perhaps advise your son to contact, in confidence, a gambling support group who would be able to advise him as to how he could help his friend.

Is it possible that your friend's son told your son because he thought/hoped that your son would tell you? He may be hoping that you'll tell his mother because he can't bring himself to own up? Just a thought . . . . .

I'd express concern that she is handing over large sums of money (assuming she has told you they are large) and ask her to be sure that she can afford it and will not be leaving herself short.
Possibly she is telling you about it as she is worried and doesn't know where to turn.

Tell her. She's an old friend. Your motives are good. Why wouldn't you?

She needs to know so she can stop feeding his addiction. He needs her to know, so it can be brought out into the open and dealt with sensibly.

I have no contact with her son, who trusted my son not to tell anyone ?

Her son lives miles away and doesn't have contact with people round here; trisher that's exactly I am afraid of

Presumably as your son knows other people must know as well. Do you see her son? If not could you text or phone him asking him to tell his mother because you have been put in such a difficult position and need to do something. If he then does nothing I think you have to tell her. If you don't and she finds out later that you knew and did nothing she may feel you betrayed her.

No, you can't tell your friend that you know why he's struggling for money. But maybe when she brings the subject up next time you could pose the 'hypothetical' suggestion that there's more to his financial problems than meets the eye, i.e. has she wondered if he's drinking/gambling/got another woman.
Risky though, as she could be offended at any such suggestion and you really don't want to destabilise a good friendship, especially as she probably needs her friends in light of her being recently widowed. On the other hand though, even if she appears offended, she might just give it some serious thought when she's alone. Which in turn could trigger a heart to heart with her son.
It is a difficult decision and I don't envy you.

Perhaps when your friend next mentions the topic, you can show by your face you think this is a serious issue...maybe you can say 'do you think the reasons he's giving you for needing money are true?'

But you can't get involved or suggest you know the truth, I don't think.