He does have a good heart, and is trying but is impulsive, depressed and pig headed and proud. Bad combination.
sounds like he needs to be disabused of the notion that being a BAD BOY is desirable, attractive or the only option available to him.
and as for the condoms, is he fully apprised of the plethora of STDs out there and how condoms are not fullproof in preventing them?
God bless you, Knitting. You have your hands full.