Those who come to gamble know very well that if they make a loss then there is no way to recover it. If you want to recover the lost funds, you have to play again and test your luck.
I have seen many gamblers who lose all their cash by gambling to find another way to add new funds, but most of the time those gamblers make losses again.
Yes I think he already knew the risk and the possibilities that he may face in the future so we don't need to care to much he know what he is doing, he just need some advice on where can he play with a little deposit or little bet at first and of course he is just researching for a good and trusted one, I highly recommend stake and freebitcoin, he may choose between it, I might be wearing duelbits but I haven't try to play in this maybe in the future.