If only Tom hadn't lost all his money on the stock market.

Tom wishes he weren't broke.

Tom's wife wishes Tom hadn't lost all his money.

Tom's wife wishes he would get a job.

Tom wishes he could get a job, too.

It's time Tom got a job.

He would rather not have lost all his money. He would prefer not to have lost all his money.

He would rather not be penniless. He would prefer not to be penniless.

She would rather he hadn't lost all his money.

She would rather he got a job. She would prefer him to get a job.

He would also rather get a job. He would also prefer to get a job.

He had better get a job.