Dear dixie082:

His relationship with the 23 year old woman is a lose-win relationship in terms of money/ material resources: he loses, she wins. In other areas, I don’t know. It is not an enviable relationship as far as I am concerned, not from his point and not from hers.

Here is your thinking as I see it, more or less: you think that if you listen to his relationship problems, he will see how compatible the two of you are; how incompatible he and she are, and he will, over time, come to his senses and end his relationship with her, starting one with you.

What in effect may happen instead is that you will be encouraging his relationship with her to continue, the exact opposite of what you are hoping. What may very well happen is this pattern: he complains to you about her; you listen, supportive of him; he goes back to his life with her relieved of distress, relieved because he got to complain to a woman who is sympathetic to him, and so he is able to endure more of his girlfriend’s lack of empathy and her using of his material resources. Frustration will build in him over time about her, he relieves it with you and goes back to her for more of the same.

If I was you, being still interested in keeping him in your life, I would be asking him questions, getting to know him. You can use any and all time you are in contact with him to get to know him. That will not be wasted time, if you can do that without being harmed.

I would ask him questions, simple, direct, in as gentle way that you want, but questions clear enough. You owe it to yourself, to get to know the object of your affections and attraction. Who is he? What motivates him?

Please post again, anytime. I will be curious to learn how this develops. Best to you!

anita