: If I were you Id stay out of it. In law realtionships are funny things. Because he is gonna have his connection to her and to you. So youd be caught in the middle. You can advise him not to give her money. Or if he wants to actually go and PAY the bill himself so that she doesnt gamble it away. Gambling can destroy a family. At the same time especially if the two of you plan to get married I wouldnt advise getting bad blood between you and his mom.