Basically if anyone you don't know in real life asks you money this is a huge red flag. Like red flag of all red flags. People should condition themselves that once they reach their pockets for money then something is wrong, stop immediately and reevaluate. I understand that scammers sometimes are very good and you don't need to paranoid towards people, but once real money is involved your guard must go up!
That's easy to say, especially in hindsight, but when it's someone you've messaged for 3 or more months, gets into trouble and then asks it's difficult to be cool headed. You convince yourself that you DO know them, and it's above board. Of course, like in this case, once it goes on long enough the penny does drop, but by then it's too late.