Ugh… I know what to do, I just feel trapped. On one hand, I can look at the big picture and see that this is not what I want for my life, or my future. I’m not an ambitious person but with small steps and hard work, I’ve been able to grow professionally, financially and academically. It’s true that I’ve been lucky with some opportunities that I’ve been given without asking for them,… but I can’t understand how he hasn’t been able to get his life together for the past two years since I moved here.

On the other hand, I feel sorry for him because I can see him struggling… some of it has been bad luck, others have been due to bad decisions. He tends to be a dreamer, not basing his views on reality, and then things don’t turn out as he expected and I have to “pay” for it. Last time I gave him a verbal ultimatum, and he said “we can even sign a contract, this is the last time I’m going to ask you for money and I will pay you back by september”. I didn’t do so because it’s cold and insensible to reduce a relationship to a signed piece of paper. But september is here, he didn’t pay me back the last amount of money I lend him and he is asking me, yet again, to pay for his share of the rent, at the last minute, when I have no other choice.

I haven’t even kept track of all the money I have given him out of good faith, trusting that he will pay me back someday. But now I feel like this piece of paper is necessary. Should I do it?