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Dear dixie082:
I like your willingness to get to know him better and your other thoughts and evaluations.
You wrote that you don’t want to overstep your boundaries with him above, and then you wrote: “I want him to understand how valuable he is as a person, and how worthy he is of the love and support he deserves in a relationship.”
This is my point about that: to help him understand how valuable he is as a person, you have to present yourself to him as a valuable person. If you present yourself as not valuable, not important, all-there for him and none for you, as if all that matters is him, then …
What you are communicating to him is that the person who values him is not valuable.
For him to value himself because you value him, he has to value you first. So do overstep your boundaries every time (over) stepping your boundaries means asserting yourself, telling him how you feel, what you really think, what you need (ex. his answers, his honest answers).
Always be true to yourself first, respectful of yourself. You have nothing to lose and everything to gain practicing this principle.
anita