Dear Prudence,
I am much older than my siblings and more settled in life. Our parents still work and struggle to save for retirement. I am usually the one who steps up to help my other siblings. I cosigned a loan for my brother to get a car and gave my other sister money when she needed to replace her roof and air conditioner. Then there is the baby of the family, my sister, “Annie.” There is a 14-year gap between us.
Annie is in her mid-20s and acts like she is 12. She has a massive sense of entitlement. We already butted heads over her thinking I owed her a free vacation when she turned 21 and dropped out of school because I gave our other siblings free trips as graduation gifts. She and her fiancé work retail but massively live beyond of their means. Both have shopping addictions and have maxed-out credit cards. They live with his parents because they have several evictions on their records. I got married last year. We paid for it ourselves and it was a huge event. Annie wants a similar wedding and can’t pay for it herself—so she thinks I should.
I sent her a check for a few grand and she threw a fit. It was insulting in her opinion. I told her that going to the courthouse cost $50 and to be happy she got anything—a fancy party wasn’t a need, it was a want. Annie will not shut up about the subject and accuses everyone of ganging up on her. We had plans to rent a beach house for a family vacation this summer but I don’t want to spend a week listening to my sister complaining. I still want to see my family but not with this going on. Should I cancel?
—Sister Trouble