Have you ever... any money? (e.g. lottery) (WIN)
won
Have you ever... or ... something on eBay or a similar site? (BUY / SELL)
bought or sold
Have you ever... your wallet or bag? (LOSE)
lost
Have you ever... money to somebody who didn't pay you back? (LEND)
lent
Have you ever... something and immediately regretted it? (BUY)
bought