I've got alot of experience in this area as I've had many a friends who were involved in drugs or spent time incarcerated.
You mentioned that he was clean for 6 months and opted to go to jail to avoid being on probation. For me thats the first flag. If he's truly on the right path, he wouldn't volunteer to go to jail to avoid probation. He's basically saying that he can't go the next 2 years or however long his probation without getting into trouble, so instead of becoming a revolving door, getting caught for violating probation, doing a short stint, getting a little time added to his probation, getting caught again, and the cycle continues forever.
So on one hand he's smart enough to know his weakness. That he'll go serve his time now and that way not have to worry about violating his conditions. To me thats a huge flag.
But if you are going to be open to the concept first and foremost, you need groundrules and things to watch out for.
Groundrules
- He must become a productive member of society before you agree to let anything go to the next level (you don't want him to be dependent on you)
- He must continue to avoid his old friends.
- He must make new friends (again you don't want him to become dependent on you)
- His life must not evolve entirely around you and your daughter
- You must go through the normal dating steps, you can't instantly become the brady bunch (if he lives with you, then he has his own room and you's go out on dates etc)
You do have a lot of positives going for you. Like you said, you don't have the negative history of a relationship. He did quit for 6 months before he opted to go to jail. However you've got alot of baggage to deal with so your starting the relationship "in the hole" or downhill so to speak. I've known hard core alcoholics, weed smokers, pill poppers and smashers and the most degenerate people are the ones who stick a needle in their arm.
Hopefully he wasn't doing heroine that long and didn't develop a huge addiction. I wouldn't be too worried about the coke as its a very manageable drug as long as you don't rock it up.
However I'd watch out for Red Flags
Weed: considering its the one drug that he's done for the longest, its the most dangerous. More dangerous than heroin you ask? Yes because its viewed as harmless but has proven time and time again that marijuana is a gateway drug. It leads to other drugs. The minute he talks of smoking just a joint, you have to tell him, he's out of your life.
I'll add more if I can think of it but thats a good start.