There is one important thing that is possibly being overlooked in this conversation. CW was upset that K promised an all expenses paid trip but he was being put in a situation to step up and pay. This indicates a lack of trust because even though he was just loaning her the money, he felt she would not pay him back. How do you love someone in a middle age relationship without even this level of trust? If you love someone and know she has put in a lot of effort to do something nice, would having to help them out temporarily irk you this way? If you went to dinner with a friend and they forgot their wallet would you be that upset if you had to pick up the tab regardless of whether you thought they were going to pay you back later?
What bothered me personally was what I perceived as the lack of empathy on CW's part (sorry, CW - don't mean to be harsh here but just stating my observation). It was all about how everything affected him without looking at things from her perspective. I am not saying he should not break up with her, but this is something he needs to address as part of his self-improvement if he wants things to be successful when he eventually meets someone that is a better fit for him
