LW is reluctant to say no because she doesn't want to be seen as "cheap" by the rest of the group.
I would have
to say 'no' a second time because I wouldn't want to be seen as a doormat. I would never think 'cheapskate' if I saw someone defending their boundaries and refusing to be a doormat.
I've mentioned this before but my friend Dina pulled this all. the. time.
She only did it to me once because the second time she tried it, I told her - in front of a bunch of our girlfriends - that I was driving her back home to get her money. It was a Girl's Night Out, and another gal, Carrie, offered to cover for Dina. Carrie sighed, knowing what she was letting herself in for, but I figured if Carrie wanted to be a doormat that was her prerogative. Asking if she was sure (because I didn't mind driving all the way back to Dina's though we would be late for our movie) I took off and let her handle it.
Dina seemed to intuit that I was not a good candidate to cover for her when she didn't want to pay as she never pulled that on me again.
But we found out later from some mutual friends that Dina and her DH, Rick, were flabbergasted to get a bill from Carrie and her DH, Sam. Apparently Dina had pulled this on her so much, that Carrie - crushing under the weight of the final straw - wrote out all the times she covered for her that she could remember going back maybe 4 or 5 years and invoiced
her. I never heard whether Dina paid her back but I did note that their friendship cooled off for a while. They did eventually become close again and Dina did learn her lesson, at least with Carrie.
We, all three of us gals, live in three different states now and I have no idea if Dina is still like this.
I will cover for people but I have no problem hounding them for my money, I don't care if it's $10. But I'll never
put myself in a position to have to hound them a second time by loaning money. I hate to be in a position to ask someone to cover for me because I find myself without means to pay for something so that is one thing I have genuine anxiety about. I hate to be a burden on someone else and cause them any anxiety about whether I'm going to pay them back.