How can you tell is he's ready?

I can understand your frustrations, eight years does sound like a long time. At the same time though, eight years is only a long time if everything is going smoothly in the relationship. There would be nothing worse than getting into a marriage and experiencing serious issues right from the beginning. Your boyfriend might think he's ready but he's probably only truly ready if he's willing to work out his habits with you and give a full effort.

P.S. Everyone has habits we can't cope with. There called differences. You've been coping for 8 years now. As long as their not hygencially incorrect, abusive, or major substance abuse habits, avoid concentrating on the negatives.

Honey, you've got one piece of delema there! As for the court thing? In my opinion I would wait till it breazes over or he does his time to get married 'cause theres nothing like having your Husband locked up. See marriage as something like a celebration of your union, to celebrate all the things you have gotten through like, court, time, other children, fights, etc. If he does do time? Nothing like a celebration of a union to help him forget about it. I believe if its been 8 years and he says he's ready, he's really probably ready. Not a lot a men can even get those words out of their mouth so jump pon dat gyal before it's too late. How bought setting a date, lets say, 2 years from now, to have something to work towards, like a relationship goal. If it's too soon, when the date is closer you could always push it back or even move it up!!!! You don't have to annouce it to the whole world until you are both serious and start making the guest list and picking dresses etc. Take it little at a time, as you've already pushed through 8 years and couple of kids. Keep moving on strong and don't be afraid to claim your man (set the date before court, get married after). I wish you da best and send many blessings to your union.