1. He used to have a lot of money but he lost it all when his business failed.
2. I didn't use to keen on classical music when I was younger, but I quite like it now.
3. I used to have interest in my work.
4. I didn't use to eat ice-cream when I was a child, but I eat ice cream now.
5. Jim used to be my best friend, but we aren't any more.