The only thing is you will really never be done...25 years ago I started seeing the most wonderful man- soo good to me-just wonderful- equally as fabulous to my kids. He had 2 sons, at that time early teens-they were the most awful children I had ever seen, but I only had to deal with them a couple weekends a month-when we did have them, he was the boss and did not put up with their crap. I loved him soo much and I always thought, some day when the boys are 18 I won’t have to worry anymore.....little did I know, it has been one hell of an uphill fight-DH lost one son a few years ago, now the other (SS38 ) is treated like a king, and I am always in the wrong. Yes, I still love my DH, but I must say I had no idea I would still be having problems after the kids were grown and out of the house. I am not trying to be sour grapes, but make sure you are a tough person and are ok with disengagement - I really do wish the best for you-

Oh wow, we actually have a lot in common. (I'm 41 and was a flight attendant too, although for a low budget airline, nothing close to VIP. lol). I get where you're coming from, it really is hard to find a person you click with that has everything you're looking for. And when you do, but they have kids...it is quite the quandary. You have the added difficulty of needing to get married to live there. I also try to instill in skids to open their minds, travel and explore, and we take them on trips each year and even got them passports (had to take BM to court because she refused to sign the papers, but we got them!).

When my SO and I first started dating almost 3 years ago, I moved in after only a few months. We didn't have the talk about rules and expectations for skids prior to me moving in, and I was very close to leaving because I found out how reluctant he was to make any changes, or enforce the changes. We fought a lot about it. My SO is really stubborn, but usually he will come around and see my side of things. I was sooo sick of cleaning up after everyone, skids having no responsibility, leaving food messes everywhere, no chores. I was about to lose my mind. I convinced my SO that we needed a chore chart- he agreed, and this has been in place for 2 years now. For the first year he didn't really enforce it, so I was like you, a broken complaining record...but I got my SO to see that it's important to me and my sanity to have a clean-ish house, it's good for skids to help out, and now it is pretty much a well-oiled machine. Skids do their chores, and he may have to remind them, but they're usually done before I'm home. If they aren't, I remind them, and they do it without complaining because they know that just not doing it is not an option. Granted, my skids are only 9 and 12, so we got to them earlier than yours. Now there are issues with SS12 lying (pretty minor, but still), and we cannot agree on this to save our lives, because we don't agree on punishment styles...again, something I really wish we had talked about ahead of time! Because now it is a source of fights. It can be really exhausting, and honestly, I don't think I could deal with your situation. My skids are VERY good, and even then it's hard. Yours sound like an uphill battle.

All I can suggest is to really try and hash this out with your fiancee before you move in. And I mean everything. Will you discipline, or just your fiancee? What is the plan for SS20? What conditions does he have to meet to be allowed to live there? If he doesn't meet those conditions, then what? How long does he have before he needs to move out? (Trust me, there are people on this site with skids living at home forever, and they are losing their minds and some marriages have broken up over it. I would set blanket rules for all the skids- at X age you need to move out if you're not in school full-time, etc). What about SS's BF, what are the rules for him? How is disrespect handled? What about follow-through on punishments?

It's really hard. (Did I say that already? Cause it is. lol). Hopefully you can learn from my mistakes!

For the last question, if you set rules now (if you are going to school you are allowed to stay living there, as long as you are also working part-time. If you aren't going to school, you need to work full time and then you have X months to move out, etc), you are giving them the rules they are expected to follow, so they know that they have to either get a full-time job or go to school, or they have to move out. That's the only way they will learn to adult. You are telling them the expectations, but they are also aware of the consequences if they don't meet the expectations (they move out.

I never had the luxury of just living at home, freeloading, while I was in my 20's. My dad told me all the time that when I was 18, I was out of there one way or another. I chose to get a full-time job and move out. So yeah, especially at 24, you don't get to live at home anymore.

What?? Whoa Nelly!

It's not your job or your role to do ANY of these things for this man's kids. They are essentially strangers to you. Please, please slow down and accept that these ferals already have two parents, and you are just, merely, and luckily only the girlfriend. You owe them exactly nothing, and that's what you'll get in return. They already resent you and your interference in their home.

You need to ask yourself some hard questions about why you feel so inclined to overfunction for these people and give so much so quickly. Do you have codependent tendencies?

I say this kindly - wishing doesn't make it so.

None of the members on this board started out disliking their skids. The frustration, anger, and resentment grew over time with constant exposure. As a stepparent, whatever you give - financially, emotionally, logistically - will be taken gladly and you will likely receive zero in return. You can give until it hurts and twist yourself into a pretzel playing Mary Poppins or Lady Bountiful, and it won't be reciprocated. YOU ARE AN OUTSIDER. THIS IS NOT YOUR FAMILY. These are damaged people living in dysfunction. And unless you can accept that and be fine with the existing dynamic, you're only setting yourself up for suffering and heartache.

My Australian friend showed me the "Tim Tam Slam". Unforgivable they are them!

His kids would not be in this position if he was a good parent. He may "do a lot for them" but he's neglected discipine, rules and structure - which are key parts of good parenting.  The kids manipulate him, lay guilt trips on him, and he doesn't address that. Is the older boy in therapy if he's afraid he's going to blow his brains out? So if he asks him to pick up after himself, he'll kill himself? That's manipulation. If he's that bad, he should be in the hospital. 

Good parenting involves the hard stuff of rules, not just the fun stuff.

I think that excuse is emotional blackmail....sometimes people live their whole lives giving in to someone and tip toeing around because they are afraid the person will harm themselves...if the eldest boy is depressed, he needs help from a professional, not enabling from his dad. 

 I don't think he's a bad man - but he has options for figuring out how to parent better and he's not using them.  I would have a hard time continuing to respect a man who lets his kids manipulate him this way, and who lets them be messy freeloaders (and adds in a boyfriend, too).  Perhaps you can overlook that one part of his character, or maybe you are just in love and thinking positive.  But many people on here say they gradually come to resent their partner for the poor parenting and inability to set limits, and it generally gets worse when the kids get older.  They don't "figure it out" because they've not been given the life skills they need.