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How to start talking about finances and setting boundary for this kind of situation?

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Question - (4 February 2014) 4 Answers - (Newest, 5 February 2014)
A female United States age 36-40, anonymous writes:

I recently just got into trading and have been having some luck with the stock market. I have been updating my boyfriend on my gains and research. Last weekend when we went out, he had told me he wanted to give me a couple of grands to invest. I assumed it was the alcohol talking, but today I told him I doubled my investment and now he's asking me if I would be willing to invest on his behalf. We've never talked about our finances...and I'm kind of iffy when it comes to talking about people's money besides my own. He's giving me play money. I don't know how to go about it. He probably makes 4x more than me, and it's okay if he looses the money. But I would feel horrible if I have to be responsible for losing it. Does anyone have any advice on how to start talking about finances and setting boundary for this kind of situation?

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A reader, anonymous, writes (5 February 2014):

Show him how and give him tips or better yet go to a casino with him and gamble that way.

I made my money through similar means but in much longer term investments and not in the most morally correct but perfectly legal way (thanks to your country's consistent warmongering, 9/11 served me as well as your own elites) and my wife asked a similar thing.

First off there is no way I would gamble someone else's money, it's just not worth it, I told her how but frankly it was too late (Obama came in, so she'll have to wait until the republicans come back in and you invade Iran, that'll be a very nice earner if you know which defence companies will benefit most from having their CEOs in government) and she'd have to find another way of doing it more akin to what you're doing and basing it more on luck.

What I did was a sure thing. American wars are the biggest money spinners which is why you're always at war, yeah, yeah peace, freedom, democracy blah blah believe that crap if you want.

My point is when it comes to gambling just make it a rule that you don't so with other people's money. Advice and tips can be given for free and you can just tell him what you're putting your money into next time you dabble and he can choose himself to put his in if he likes too but not through you.

That way you're sharing the wealth but none of his risk. If he loses you've lost too, and his money never went through you so it never becomes an issue.

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A female reader, So_Very_Confused United States +, writes (5 February 2014):

So_Very_Confused agony auntI would not take it but rather you can show him what you do and how you make the choices and let him make his own decisions.

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A female reader, Aunty BimBim Australia +, writes (5 February 2014):

Aunty BimBim agony auntOffer to teach him how to do it for himself.

Tell him you are on a roll right now but there is no guarantee it is going to continue, and that you are not prepared to risk your relationship if things go belly up and your winning streak ends.

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A female reader, anonymous, writes (5 February 2014):

What you are doing is gambling. Is it day time trading?

If you are not investing long term Iit is basically gambling. I would never take anyone's money for this. Just tell him that you will feel terrible if you loose his money.

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