Separate yourself emotionally from their choices. Second, focus on encouraging good steps. When you see that person doing something right, tell them that they're doing something right. When you see that person making a good move, give them praise. That way they will know and start doing the right things and eventually start to help themselves. Then you can give them opportunities to work on, so they will grow exponentially. By the way, hit me up at Vegascasino if you're a player there, poker or black jack. Hope my advice helps.
Letting them know you appreciate them as human being is enough. Maybe he/she is just down because of their life decisions but yes don't stop encourage them. You seem like a wonderful and full of positivity person. I'm playing poker too, where can i hit you up ? VegasCasino? Not familiar with that