Anyone raised by a mom who has been married seven+ times is BOUND to be a mess. How could they possibly not be?

And let's just assume as a given that StepSon's (SS) relationship skills are poor. Again, consider the role model.

And you've already said he drinks too much.

Again, going back to BioMom (BM), you know/knew she poisoned SS against both you and his father, so while SS probably doesn't actually hate you (you or Dad), he probably doesn't have a whole lot of emotional investment in you either. And if you get too inconvenient (or pesky) -- out you go. Sorry to be blunt, but this shouldn't come as a surprise to you...

Gratitude? (Who?)

Expect to be disciplined? Heck no -- He's an adult. Technically, anyway. And I doubt he'd ever consider either you or Dad as people who could legitimately administer discipline... (Remember, you didn't raise him.)

I'm also going to assume that you didn't get $100,000 to guarantee his loan by being lucky -- That you and Dad are intelligent, successful people who generally make smart financial decisions. Well -- This certainly doesn't sound like one of them...

So -- Do you want to preserve the $100,000?
Or the relationship with your SS?
Because I'm betting you won't be able to do both.

Do stepchildren expect not to be disciplined?

Adults expect not to be disciplined, particularly by people who did not raise them. (While I am somewhat skeptical of "not allowed" to see him, I acknowledge that it is possible you and your husband made every possible effort and were stymied at every corner, but even if that is true, you still did not raise him and do not actually have a parental relationship with him).

Now, my husband worries that his company will go under and he will lose his $100,000 and if that happens, I will be the one blamed because I pushed him, so I suffer with worry double time now. Even if your SS were the most responsible person in the world, the likelihood that a new small business will go under is fairly high. If you and your husband were not willing to deal with that possibility, you really shouldn't have agreed to this arrangement, let alone pushed it.

I am not saying you are *wrong*, in any kind of ethical sense, and you certainly seem to have your heart in the right place, but you do seem to have a view of reality that is somewhat skewed in your own perception.

I believe I was used and he snowed me. When we got to the point where I was more comfortable with him I saw he was having a problem with going to work, due to relationship difficulties, and drinking. I told him I thought he drank too much and so for the past few months he really hasn't communicated with his father or myself. Absolutely possible that you were snowed, sure. Also possible he thought he was developing a close, understanding, and non-judgemental relationship with his estranged dad and step-mom and was hurt and surprised to judged and "disciplined".

I am not saying my hypothetical is correct. But you are from my perspective jumping to some pretty big conclusions about his motives. You also took a pretty big risk with your money, and while he may be truly irresponsible or going back on his agreement, you may also lose your money just because investing in a small business is a risky move and the economy is not exactly the greatest right now. He may even have cut off contact because the business is in trouble and he dreads you and your husband's reaction. Perfectly responsible? Not really. Somewhat normal? yeah, kinda.

I don't think discipline is the right word. Adult conversation would be more fitting. I also told him that I thought it was terrible that he didn't call his father on Father's Day or on his birthday, just this month. He told me it was the responsibility of the parent to call the child, which I suppose if he were a child, that would be the case. I tried to make him feel better and told him his dad doesn't even call his three daughters, all grown, successful adults. I told him they faithfully call him once or twice a week.

No.......we were not allowed to see our stepson but a handful of times while he was growing up because we were dirt poor and had no money to hire a lawyer. Everytime his mother was involved with a new man, and there were many live-ins between marriages, she would tell us that he was our stepson's father. His mother even lived with a guy who was our stepson's age for six months.

The accountant we requested he use is ours and from a very prestigious company. We have done business with him for over 20 years. He said the company was not in very good shape financially and he needed to talk to my stepson. My stepson hired a different accountant and to this day, he has not called our accountant. I believe that is disrespectful.

My stepson has a six-month-old baby who does not have his name and he has seen him once. He pays no support. I told him I felt he should send the mother some money. The other child he has, who is 14, he sends his mother $25/week. She has never taken him to court. He rarely sees him - may three to four times per year.

I guess I'm supposed to be a little mouse in the corner and forget about morals and respect and common courtesy and decency when it comes to him and keep my mouth shut and not attempt to make him a better person because I didn't raise him, right? Is that what you are saying, quirk?

It seems to me that you are trying to tell him what to do with his life and his business. He might have snowed you but I think you went too far with the 100k of loan. Knowing his lack of business savvy, you and his F should not even get involved, let alone putting up $100k. It appears that you were trying to buy his love and to change him. At his age, you can offer general advises but I think you should not be too involved.

Someone wrote this and I want to leave you with it:

"The beginning of true love is to let those we love be perfectly themselves, and not to twist them to fit our own image."

You have been trying too hard to make him into someone he is NOT.

it is pointless to tell people that they drink too much, if he is an alcoholic he knows he drinks too much, by telling him you accomplish only one thing: he now places blame on you rather than himself.

if you don't trust him with money, then it is a bad idea to loan him money. sounds like maybe dad feels guilty for not raising him and now tries to buy his love?

he has a son he is not raising? i am not surprised. he had a dad who didn't raise him so he does the same...it often works this way.

i think you should let dad build his own relationship with his estranged son without you giving him advice.

my own parents who raised me do not give me much advice since i am an adult, I can't imagine being too happy over unsolicited advice from people who did not raise me and aren't even related to me. i suggest you back off and let dad deal with it.

i agree with shakti, you can't make him into somebody he is not. and yes disciplining or giving unsolicited advice at this age is generally a bad idea.

If he is an alcoholic, he WILL blame YOU and everyone else for his problems. He WILL lie and make promises he can't/won't keep. He WILL use any excuse to cut off communication with you if you try and confront him with the truth about his alcoholism. He WILL be nasty to you and use you, and blame you. He won't be able to see your point of view, only his own. That is what alcoholics DO! It is part of the illness. Try not to take it personally.

This situation will require you to have healthy FIRM boundaries! You can love him but that doesn't mean you should enable him! You my benefit from going to Al-anon to get help for yourself in how to deal with an alcoholic.

The hurt is there because you tried to treat your SS well and you expected him to be more appreciative of this. He isn't able to do this! Emotionally he has serious issues that have nothing to do with you - but you are receiving the brunt of his anger.

I know these things because my brother-in-law and his son are both alcoholics and my sister is a classic co-dependent enabler!

You love your SS, but loving him and still having healthy boundaries is VERY important!

Good luck!