Recently, I am in a catch-22 situation. I have a long time friend who every once in a while will ask me out for coffee or dinner. We are not the best of friends because of our difference in lifestyle but have known each other for almost 10 years, so let's say our relationship is luke-warm but I do enjoy his friendship. He lives in an expensive condominium in district 10, drives a luxury car and is a white collar. He socialises with the rich and often goes to posh restaurants. He travels business class and stays only in 5 stars hotels. While I stay in HDB, takes public transport, likes to go hawker center. So one day, much to my surprised! He wanted to borrow a sum of money from me. Ok, let's not go into details how much and for what purpose. It is not a lot but substantial. He does not gamble so must be needed to tide over a bad period. The dilemma here is he is supposed to be the richer among the 2 of us. If I don't lend him money, there goes the long time friendship over this not much but substantial amount of money. If I lend him the money, I find it very hard to justify that I am lending him money to upkeep his lifestyle.
So the question here is....if you are in my shoes, what will you do?