I'm wondering what you mean by strong when you say strong woman.

Also, in what way would the match be perfect? Which i guess is another way of asking what you (or the woman in the article who was successful in her career) are envisioning as a perfect relationship.

You are encouraging him to work on assertiveness and self-esteem. If he is successful, and he becomes more assertive and develops greater self-esteem, then the relationship presumably will no longer be between a strong woman and a MWLSE. What would that mean for you?