Daisygirl...it's obvious that you care deeply for this man because you've contimplated marriage in your mind with him...I think we're all guilty of that when we date someone we really like...doesn't mean we'll go through with it, but for most it's in our thoughts....I think that's normal. I don't see that as a red flag unless you're desperate, which I don't get that from you at all.

It's one thing to be around your BF and his son on the weekends...but, what happens when you move in. Then you'll consider that your home too with rules and considerations of your own...and what happens when his son doesn't agree with you and he will, protests, pitches fits, etc....and then dad is pitted against you. Will your BF stand up for you or his son? Me thinks if dad is feeling guilty, it's going to be his son.

If this was me I'd go very, very slowly...put marriage out of your mind, enjoy dating for at least 2 years before thinking of anything permanent...I think you'll see everyone's true colors within that time frame. Normally after 1.5 years they come out and you can decide whether he's really worth being with or not. I would not move in with this man if his son is still living at home. At his age he's a grown man and like Chatty says...he needs to be treated like a man and made to fend for himself. If dad mothers him he's not helping his son be a man, either.

And if you're really serious about your BF then try to get to know the son. Take him out for a burger and talk...just the two of you. It takes step kids years to feel comfortable/accept step-parents...and then, sometimes it never works out.

It sounds like you've found a nice guy, but even nice guys can be manipulated by their grown kids...and when there's an outsider (you) in the mix, it can make for some issues down the road.

I don't envy your position...this is going to be a waiting game with lots of patience on your part.

Good luck, keep talking to your BF and I hope dad guides his son towards the door and independence and manhood.