Wow, either your boyfriend really wanted to sleep with this stranger or he's a total sucker. Did he ever get the money back? Or proof that she actually started the business?

Something like this should arise concern that your guy is reckless with his money. On the one hand, it's his money and can waste it however he wants. But it doesn't bode well for how he'd be in a long-term relationship. If he lent the money to this woman before he met you, then you really can't say anything about it. But if he did it while you were dating, it would be fair to tell him that it makes you uncomfortable that he's chatting with women online and sending them large sums of money.

He definitely should be allowed to help his friends if he wants to, but the whole "online stranger" aspect raises a few red flags. What are her intentions? What are his intentions? Is he helping a friend or trying to sleep with her? Is he getting scammed? Is he too nice and gullible? And what if you end up moving in together and splitting household costs? Do you want to be with a guy who gives out large sums of money to people he's never met in person? All things to consider. If this is in his past, and he's a good boyfriend otherwise, I wouldn't sweat it. He could have genuinely wanted to help someone he met online and trusted. While it may not be something you would do, it's already done and there's no use dwelling on something he did before you were together. It's strange and a bit dumb, but maybe he meant well. But if he is still sending money to random women online, you should definitely talk about it. Also, you might want to take this into consideration if you're looking at long-term plans with this guy.