Dan, Ann's boyfriend when her gambling addiction skyrocketed, lost all of his savings as a result of Ann's compulsion. Yet, through it all, he realized Ann was still the person he had always known. Despite the hardships, Ann and Dan's relationship is still intact.

Oprah asked Dan if there were any signals he feels Ann gave when she was struggling with her addiction.

"You know, Oprah, it's funny," said Dan. "A gambler is the most fantastic con artist. They can tell you any story. I assume it's probably the same with most addictions. But they tell you a story that's so believable, it's impossible not to trust it. I guess my advice to anyone is if you feel the story is too perfect, that's when you should start to question it."