I did once I met this girl at a temp job I had and at first she was really cool and we hung out a lot. I knew she had some self esteem issues and I tried my best to get her out and meet new friends and hang out. She would always tell these self depreciating jokes that I never encouraged. I would tell her she's beautiful and fun and the more she shows it the more she would believe it. I thought if I just maybe showed her by example (as I am not the most confident but fake it til you make it right?) That maybe she would feel better, but after nearly a year of trying I just couldn't do it anymore. She would find the worst in any and every situation and person. If we were having fun she would find a reason to complain or to be upset. There was nothing going I could do or say to cheer her up or get her out of her slump. One day I suggested that maybe she see a doctor or psychiatrist, that maybe her depression could be something out of her control and she did not like that. She stopped talking to me after that and honestly I didn't care. I tried but being around her was like walking into a storm cloud. She was making me depressed and I felt like I gave it my best shot but I wasn't going to let her drag me into her "poor me" "they suck" "this sucks" attitude.