Dear Prudence,
I have a friend, “Jackie,” who has been homeless on and off for 10-plus years since their marriage ended and their house was foreclosed upon, simultaneously.
Whatever issues are there (anxiety, chronic excuse-making, etc.) make it impossible for Jackie to hold down a job, even though they are very intelligent and well-educated in several fields. Jackie has often borrowed money from me in the past, but in the last couple of years they went from loans to gifts as I knew there was no way for them to pay me back. My husband and I make just ok salaries but live in a very expensive area and rely on side hustles for things like vacation and home repairs. We also give money monthly to his parents, who had no retirement savings.
When Jackie transitioned last year, their situation became worse, as they entered into a demographic that is becoming increasingly vilified in our society. Jackie now calls me hysterical whenever the last sofa surfing host throws them out, looking for a place to stay. My house is very small, lacks privacy and, quite frankly, I loathe houseguests and have since I was a child. This would not be temporary, as in “my heater is being repaired.” This would be until I get fed up and asked them to leave. Every time they ask for money or a place to stay, I end up sending money to pay for a few nights in a hotel room (or car repairs, etc.) and then immediately calculate how many months of side hustling it took to pay for that. Then I get angry, and then I feel guilty for feeling angry.
Jackie needs to get a plan, get on disability, and get a low-income apartment. They have no parents and no siblings to help out, and their daughter is a recent college grad struggling to find a job, as well. Their ex-wife is not a nice person. How can I help Jackie without bankrolling or housing them? At this point, I don’t even want to text them to check up on their welfare, as any contact turns into a plea for money and housing. It breaks my heart, but we’re already helping to support my in-laws. We have our own retirement to worry about, too. It keeps me up at night.