So here goes, My boyfriend and I are planning to get married... he is more than I could have ever asked for … I honestly never thought I’d meet anyone like him. He is sweet, dedicated, virtuous, loving and honest- except when it comes to a recent happening… giving money to his sister. When we first were dating, we had that talk about our families and he said his sister used to use heroin but she got clean from it, I took it as “wow I thought heroin was extremely hard to get off of, she must be strong” and didn’t think about it again until a little later when we took her somewhere and I saw her in my rearview mirror rolling a joint in the back seat which I didn’t mention until we got home because I thought it’s the first time I met this girl and I just wanted to keep the peace- and we were almost to her house anyway… later when I mentioned it he claimed it had to be a cigarette but I know there is a difference between the way you roll a joint (im not a drug user but I’m also not retarded) So I let it go, and didn't care that much- in fact I thought well marijuana is a lot less damaging then heroin, but almost a year later she flees the state, quits her job and leaves all her crap at her house for guess who, him to move…he moves it to his moms at his expense (I chipped in too) of around 250 bucks and now guess who's back on drugs according to the parents and asking for money. He doesn’t know I know this but he has been giving her money because she's making all these stories that her and her druggie boyfriend had some unforeseen costs, and she is in fact not on drugs despite what their parents told him, but getting supposed treatment for opiate dependence- yaaa right,…. Not sure how she thought moving to the most expensive place in the country with no job would turn out but she is 30 so she should have thought about that… now for the drug story.. treatment programs are 1000’s of dollars but either way, if she was clean and now needs treatment either she was never clean or she's not getting treatment she's in relapse. And either way, it makes me want to vomit because she's so blatantly irresponsible and she's using the sweetest person in the world for her sick habits and lifestyle. What bothers me most is it seems like he's in denial or making excuses for her and has failed to mention it to me... I think he didn't mention it because he does care about me and he knows how I feel about drug users (my theory is you can lead a horse to water... ) they have to help themselves and there's nothing we can do besides moral support. I really want to marry this man, I love him sooooo much and we are so happy together… but in this case his niceness and possibly naivety – I haven’t quite figured out how he is not realizing he's paying for her drugs and irresponsibility.. but it is jeopardizing our future together because I will not sit my whole life and watch people use my husband especially if we have children which we both want... we worked SO hard to get to where we are, and we are struggling too, we live frugally paying off our student loans, working a lot of hours... we both have lived our whole lives on the straight and narrow to get where were at. How do I bring this up that letting his sister leach off him is a dealbreaker without him digging in his heels or getting defensive that I just don’t like her or something.. I’m scared he will not open his eyes to what she's doing let alone understand my perspective…even though he's very smart. And don’t get me wrong I have strong family values, in fact I push for us to do things with his family, take his mom, grandmother and even one time his sister out etc… and my priorities are to help those in need if they appreciate it and have tried for themselves, but this is far from that. I just don’t want to lose him and I’m scared he will continue falling to her lies and feeding her sickness. Thanks for reading my rant and I would appreciate any feedback… I know most of you will say move on,, but I swear I don't think I will ever meet anyone like him again since I haven't until now... Peace

The crux of the issue is how much should you interfere in his spending, married or not? The simplest answer would be to tell him you aren't chipping in and you will be keeping all your finances separate from now on, because you feel that he is supporting drug use, not rehab. Of course it isn't that simple, because what he gives away won't contribute to your present and future together (as you said), but there is nothing legal or otherwise that a spouse can do about the other spouse's spending. He could buy a boat or get a mistress or give to his favorite charity and your only options are to take it or leave it.
I think I might do a little quiet fact checking were this my situation. Yes, of course drug users are habitual and often very clever liars. Find out, even if you have to hire a PI, and tell him without triumph or I told you so's. Then, depending on his reaction, tell him you will not combine incomes even after marriage.

If you marry him, get a prenup and have totally separate finances. That includes separate tax returns, by the way. He may not need his "eyes opened." He may very well already know the truth and just not want to face it.

How do you bring it up to him without it being a deal breaker? I don't know. If the situation is a deal breaker for you (either now or later) I'd rather address it now. He may be perfect in every other way - except for this. Can you live with that?

Just as a side note I find your phrase "im not a drug user but I'm also not retarded" to be very insensitive.

I do realize your brother either used or uses - is that playing a part in this problem? https://www.askmehelpdesk.com/other-family-people/sister-homeless-refuses-work-668414.html

I personally think that money should never exchange hands bettween family, or friends, at least not without some accountability and expectation from person lending.

Maybe your boyfriend would consider having some proof before giving money- a simple contract that includes the name of the rehab/treatment centre, so information can be confirmed before money changed hands.

Maybe your boyfriend would consider some sort of family counselling with other family members to address what to do to support his sister,

But I note that you are not yet engaged, so separate finances should be the rule. If you choose to 'chip in' with his sisters' expenses, you have only yourself to blame for not saying no.

And of course, the flip side is you can't tell your boyfriend that he can't spend his money however he likes.

It would be no different if the issue with his sister was gambling for instance. It she were addicted to gambling, it might be easier to face because it is a 'legal' activity, and socially acceptable for anyone to gamble. But the bottom line is the same- money being flushed down the toilet by an addict.

If and when he decides that he had to address the addiction issue, along with the money going to support the addiction, will you be able to state your opinion, and help find solutions for him, and support him when he goes through the family upset that will follow when he is no longer keeping the peace along with other family members.

But, all you can do is mind your business. Not help out or loan money or bail her out of circumstances she will find herself in and needing emergency help. If he chooses to spend his money, and continue to spend his money on his sister, and ignore the obvious, no amount of nagging will help, until he too, is ready to be helped.

With the example you stated of the moving all her stuff, you are actually enabling him, to enable her.

Deal breaker? Not necessarily. But clearly when finances between you and your boyfriend become joint, there should be an agreement, in writing that one or the other cannot dip into the overdraft, or savings, without the approval of the other.

For now, I can't see where you can change what has most likely been a very long standing problem with him and his sister, and family.

Wow, thank you all for replying. Your thoughtful advice has brought me to tears, it just makes me very sad that I found this wonderful person, one in the world guy that maybe I cant, or won't be with because it hurts so bad to see this go on and my hands are essentially tied. All of you make very valid points and I agree with your logic. Its funny because when I first heard he had a sister in my age I was excited to think I could have a new great friend in my life. And yes to one responder, my sibling has had drug issues- but my family confronted him in an entirely different way. Peace