A Couple of things here caught my eye in your posts.
What Part of BS and she is being Used can't she See ? Not to Mention, the Safety and Well-being of her son and herself ?
Being in and out of Prison, is not a one time, I made some money (into the Million $ Bracket) Defrauded or it wasn't Clean Money ) type thing.
Living with Mom, no Job, no Car, is not something even " Criminal " Millionaires can claim.Unless they are in for like 15 years and all assets were frozen. They almost always have some money put somewhere else in case they get caught then get out.
If he was a Millionaire before, a Decent person would have bought their Mom a nice home, a car and made sure they ( Mom ) was taken care of.Therefore ensuring the loan of a car from Mom or even just a beater car to use in case of bad times.
1) She needs to or and her Family need to do a Criminal Background Check on this Dude. Make sure that he isn't a Convicted Rapist, Child Molester, Wife or Other Assaulter. Never Stolen or burglarized, No Drug Convictions, DWI Manslaughter, Murder Rap's.
2) She needs to get a hold of her Life, Her son's Life, Take back her own Values,if she does not smoke or allow smoking around her son , Then She must Enforce that..
3) She needs to understand that Once Married She is responsible for any Bills he may incur while Married, His Bills, his " Tickets or Fines" he may get. Any Bills. like phones or Cable or Internet, rentals, Anything that he Charges or Orders. Can and Will Come back on Her.
For You ? I would just explain that you are getting not so good "vibes " from or about him. Wish her the Very Best, Hope and express that you want her Happiness. But you just cannot Falsely associate and act "OK"with someone who makes you uncomfortable.
With that, you are just being Honest, a true Friend and also possibly Protecting yourself & SO from getting involved in something you do not wish to be.
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