I would nip it in the bud as soon as possible and here’s why: I was left with my dad’s car after he died. Before I could sort out selling it, my friend totaled her car in an accident so I lent her the car. Months went on and she did nothing to replace her car; she doesn’t make a lot of money but I’m sure she was reimbursed in some fashion by her car insurance company. I continued to pay tax and insurance on that car (including putting her on as a driver which cost more since she’d been ticketed once for driving while on her cell phone.) At one point, someone rear ended her and of course I received the insurance reimbursement for that accident. I finally told her she had to take ownership of the car completely and she did - but she still got the car for free. Then she had the nerve to ask me for the reimbursement check from the accident and I refused and told her that money had gone to the insurance and tax for the car for the year that she drove it while I was still the owner. Again, she was in more difficult financial circumstances than I was at the time and it was an act of friendship and kindness. However, an ex boyfriend just left her $100,000 in his will. Do you think she’d remember that I literally gave her a car for free when I could have sold it for about $10,000. Some people just see themselves as needy and deserving and will take what others will, sometimes foolishly, give them. Saying “thank you” over and over is appreciated, of course, but it still smarts!