How did she even know it?! Ray had a really hard life.
Is it true love or just a con? Ultimately, Ray landed in prison for selling drugs.
Their relationship was discovered, Courtney was fired, ultimately sent to jail and is currently still on probation.
Soon after that, he began dating another girl, Nelly.
Unfortunately, that period of stability didn't last very long.
And obviously the answer to that question depends largely on each individual parolee and their situation.