Considering such stories to be true, which is rare in the first place,
Case1 - Anybody winning money on betting has done so on their own accord, so how to wish to spend that money or pay back "debts" is their own choice and not obligation. It is wrong to steal money from anybody, of course paying back the money is an attempt to redeem, so at least the stolen amount should be returned if not with interest.
Case2 - I highly doubt this story, coming the type of account which posted the story, I am sure that the story is fake one, only used to generate buzz and get some likes and replies on twitter. Still then, what type of apprentice tells their boss about their bets, unless they took money from their boss to place the bet - in which case I would say that person is irresponsible about their money.
I totally agree on case 2 and I know for sure that the two stories are some pizzy-head fabrications; just maybe to acquire traffic as you said or, gain verification.
My emphasis are on case 1 and your replies; do you mean that if it were you, all you'd do is -- let out the money you stole from your girl's purse? Would that really make true, the love that you claimed to have for her? Do you know that if she decides to Sue you, you'll have to pay for property damages? I mean.... atleast, even if it's not a 50-50 deal, you should make things right.... after all, she didn't borrow you the money, you stole 'em 😹