September 7, 2024; 4 Elul, 5784 Sponsored anonymously for the Refuah Shleimah of Yair Nissan Ben Sara

QUESTION: A friend of mine has a moral dilemma. Before I present my dilemma, permit me to provide some necessary background. My friend’s parents are successful business owners. They have mostly retired and have hired my friend, their son, to run certain aspects of the business. They pay him well, but he still struggles to make ends meet. Now, his child is dating seriously and is about to get engaged. Generally, his parents will help him with his family Simchas (e.g. weddings, Bar Mitzvahs) and so my friend will be looking to them to help pay for the upcoming wedding...