No I’m not trying to control the relationship. But it’s a weird balancing act of being a good friend and be in control of the relationship, offering a good friend financial help, and ensuring they’re ok financially. Obviously this is a very rare situation that I’ve never navigated and don’t know if others who have.
Will I just end up upset, and down a lot of money? I personally think we will remain good friends forever even when I stop paying him. But deciding what, and how I should be expecting from him now that relationship has moved from me as the boss, to me as a good friend it’s weird uncharted territory. I feel like I need to give him an ultimatum at our next meet up and move the relationship back to more business-like. But there’s no where to go and ask about something like this.
I feel very torn, and unsure what to do in this situation. To his credit he’s been extremely honest.