This is likely to be long so I apologise, but the circumstances are slightly complicated and I don’t want to drip feed. The context is perhaps not directly relevant but goes towards my feelings on the matter so I’m including. I’ve bolded the TLDR.
I had booked to go on holiday with a friend last month. We were moving around and were meant to stay in 3 hotels and the trip involved a return flight. We have been friends for many years and are close.
Unfortunately I had to cancel the trip at the last minute due to the serious illness of an immediate family member. This was not something that could have been foreseen at the time of booking. As I would expect, she was very understanding - I’m sure she was disappointed and I apologised for the inconvenience but at the same time in the context of what was going on for me at the time, the cancelled holiday was nothing.
The flights and the first two hotels were non-refundable but the final hotel (which she had booked) was within the free cancellation period. My friend agreed that she would cancel the third hotel and therefore we would not be charged.
My portion of the cancelled trip was covered under my travel insurance. I have successfully claimed for this. However, her portion of the trip was not covered under either her or my travel insurance due to the circumstances of the cancellation (if her family member had been ill it would have been and if I had been ill it would have been but illness of my family member didn’t qualify under her policy). She spent a while deciding whether to go on the trip alone but ultimately decided not to. I understood her reasons for not wanting to go alone and I offered to make her whole for the cancellation. She didn’t ask me to do that but did accept my offer and I transferred her the money. Although I wasn’t thrilled to spend several hundred pounds on a trip I couldn’t go on, I felt reimbursing her was the right thing to do - I didn’t see why she should be out of pocket as a result of my family emergency or forced to go on a trip alone. So far, so good.
It has now emerged that she failed to cancel the third hotel when she decided that she wouldn’t go alone (we were still within the free cancellation period at that stage). We were a no show and she has been charged for the booking. Although she hasn’t yet explicitly asked me for money, I feel she is circling around it (not clear whether she feels we should split it or I should pay entirely). She also isn’t fully owning her mistake. So far I have given vague sympathetic responses.
My gut reaction is that this loss results from her entirely avoidable mistake. I’ve already spent several hundred pounds on this cancelled trip and I’m not willing to pay more. If she asks me for money, would I be unreasonable to refuse to pay?
But then part of me thinks that I should suck it up for the sake of the friendship - it won’t be that much extra money. And also that the holiday booker takes on some risk and if I got it wrong I’d appreciate people being understanding and splitting the mistake. But part of me is really quite irritated that she is bothering me with this - I think in the same circumstances I would be shielding her from as much admin as possible. And I feel I have already been generous enough in reimbursing her for a holiday she could have gone on. Also I really do feel I wouldn’t have made this mistake were the situations reversed - she is not an organised person.