Quoting your fun sized advice: “A man would also understand what it really means to settle.” I’m a man and I don’t know what you’re talking about, so what does it mean to settle, or should I ask a real man?
It’s a play on words, chief. Settling has both negative and positive cultural connotations within its various phrasings.
Too often, people with prince charming disease get freaked out about “settling down,” and they use the phrase “to settle for” when they should use the phrase “to settle into.”
In other words, both men and women who expect romantic perfection are terrified about becoming established in a relationship, and they confuse the notion of being satisfied with less with merely being satisfied.