I'm not sure how to describe this mess of a situation! But healthy would never come to mind. At some point your male friend needs to understand that a professional personal counselor is his best option. Without that, he risks the destruction of a very good friendship. I'm not that person, but I have found myself in a situation where I was also confused, never able to enjoy a healthy relationship (marriage), and in general not moving myself forward. I found the courage to seek professional help and am so glad I did. That decision has to be his and his alone. Somehow you need to find the strength and support to help him find the path to a healthier life.
Best Wishes!
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On the information you have provided, this seems a really understanding friendship. With a very solid core. It might last longer than usual. But, things change.
That being said, doesn't seem manipulative at all to me.
But I might be wrong I have a very little info on how the person is, how he says and does.
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