I think everyone deserves the benefit of the doubt and a free pass. Mortgage companies, utilities and service providers will in fact generally work with a customer if there is financial hardship so I don't see why it can't at least be considered in situations like this. Going through a messy divorce seems like a genuine reason for losing a handle on life in general and I think I would probably also work with this parent. Do I have to? Absolutely not, my number one priority is my family and my business but the beauty of running my own business is that I get to make those calls and assess the individual and whether I think it is a good idea in each circumstance. I am not about to sit and judge her actions when I do not know fully what is going on only having a portion of the information. Yes she could be taking you for a ride, but that is an assumption only you can make...sob story is anyone's guess but I'm not about to be insensitive to her circumstances having made a succession of screw ups in my life and being eternally grateful to those who have taken a chance with me as those people have helped me when times were rough. I have been faced with a dilemma that was of my own doing and nobody needed to care but they did and it was what enabled me to count my blessings and get my act together. A parent going through a divorce is trying very hard to be a better parent and I can totally understand why her sons birthday party is a priority whether she can afford it or not. The added guilt it would cause her in addition to things would be simply awful. We are not in her shoes so we see things more factually, not emotionally but it doesn't make her circumstances any less real. I couldn't sleep at night knowing that someone in need was flat out turned away. I am notoriously empathetic but I think a lot of that comes from the fact that I have been through a lot so my heart is open to others...it back fires a lot lol I think boundaries are important and that you should put it in writing that she pays weekly, you will waiver the late fee on this occasion but it is a one time situation and she should never even ask again in the future. Having compassion is fine but you definitely need to set boundaries and stick to them to prevent being taken advantage of in the future. If she can't pay her daycare bill now, how is she going to pay the late fee on top of it?? It then becomes your problem when standing to firm results in her leaving all together and you being out of pocket. Just because she is in a personal pickle asking for help does not mean that she will be a serial problem parent. Maybe a break is just what she needs, and maybe it isn't but I'd for sure give her a chance before I painted her all sorts of trouble. I've been doing this for 9 years and given people the benefit of the doubt on occasion and its never come back to bite me in the ass, but that is because I haven't let it.