He was ashamed of pretty much everything except sex.
He's ashamed at the idea of being emotional with his sister, and he's ashamed to the point of complete despondence when he isn't able to have sex with his co-worker. Yet he's not really ashamed when his boss or his sister uncover his porn habits, or when he wanders into the seedy gay club.
His addiction is so severe that he's not only unable to resist sex, but he isn't even aware of when he should. This need for gratification has an effect on the way he treats everyone, most notably his sister. There are a few scenes that suggest that he has a sexual attraction to her, but it's not so clear-cut. I think that he is normalized to constant, unusual sexual behavior, so much so that he doesn't know when he's crossing a line with her. (She may not know, either.) The OCD also comes into play here - a lot of people with OCD suffer from intrusive sexual thoughts of people they're not normally attracted to. He wants to love her like a brother, but he can't because of shame over these thoughts.
I think the reason it shows the woman's ring at the end is that he's finally fighting the compulsive behavior of his sex addiction. There's an earlier scene that I think is key to understanding this ending. He scolds his sister for sleeping with his boss, we see the type of mindset he has about the "need to act" instead of taking time to think:
"You know he's got a family? You didn't see the wedding ring on his finger?"
"No."
"You're a liar."
"I'm sorry."
"You're always sorry. That's all you ever f--king say."
"Well at least I say I'm sorry."
"Try doing something. Actions count, not words."
"I'm sorry. I'm sorry. I f--ked up. I'm not perfect, I make mistakes, but I'm trying."
"Some people f--k up all the time."
(The last line is an attempt to admit that he's a f--k up too, but it comes out emotionless so it's hard to catch)
By the way, the scene where he follows the woman on the subway is my favorite. He really does have delusions that he's a heartthrob that literally no girl can resist. (Rather than the creepy guy on the subway who stares at girls and then follows them.)
Sorry these thoughts are so disorganized, I've just finished watching it!
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