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I've moved your question out of Other Money & Services to this forum topic area so that it will be more likely to be noticed and addressed. Also, it seems to me, to be more about a relationship issue anyway.
I say it would depend on how long you've been together, whether or not you trust him, if he needs help, etc. I was going to help out a boyfriend once, glad I didn't because we weren't together long. Be careful about giving money away, especially if you're not in a committed relationship.
It really depends on what type of relationship you have with your significant other. There are too many factors to consider:
1) Are you living together?
2) Is it long distance?
3) How long have you been together?
4) How serious is the relationship?
5) Has money been a huge factor in the relationship in the past?
6) etc. etc.
I also think it depends. I wouldnt go out and buy him a car. But hey if it were a million bucks then why not. If it were a few thousand then I might flip for a nice weekend away.
On the other hand if he is being sneaky with things then I may not be so ready to jump at letting him cash in on my winnings.
Whats your story so we can answer better and give you better advice. It seems vague to me about your boyfriend.
I'm curious why you would throw in the thing about the boyfriend being sneaky. Generally when people are asking about what they would do with winnings (including who they might give some to), they don't generally throw in a wrench like if the boyfriend is being sneaky.
So are you really asking about your sneaky boyfriend? And is this boyfriend (imaginary or real) really being sneaky, or maybe just living his life that doesn't include telling his girlfriend about every detail of everything he does? I find a lot of times when people think someone is off being sneaky or "hiding things," they are really just wanting a little bit of deserved privacy.
(I once had a boyfriend that thought if I ever didn't tell him any tiny little thing, I must be doing something awful. Sometimes I was just at home doing absolutely nothing and simply got tired of getting 20 questions about everything I did. It was a very nice way to chase me off.)
If there truly is something bad in the sneakiness, then the winnings being shared with him is completely irrelevant. Either you want to be with someone or you don't. If you don't want to share money due to something like that, sounds more like you shouldn't be with him. The sneakiness and the money are two entirely different subjects.
But back to the question... since I'm extremely practical about money and all money I have is thrown into the pot and budgeted just like everything else, whether I won that money or not would not have anything to do with whether I shared it or what I might buy for someone. I wouldn't just give away the money to a boyfriend, but yes I might buy some stuff if that were in the overall budget. A car? Only if it were a LOT of money, and I mean like a big giant lottery, not a raffle. Because most of it would be invested for the future. And any boyfriend of mine would know how I am about money and not be the least bit surprised over it.
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