Don't Ruth and Boaz blow your theory out of the water, and if not, how should I be thinking about this? Even though I've written on the "Ruth/Boaz" question in a number of contexts, it's still a question that comes up often.
As you mention in your question, it can appear at first glance like Ruth provides an example of a woman initiating a romantic relationship with a man in a way that "liberates" godly women from the sometimes frustrating position of waiting on Christian men to show initiative and leadership in potential dating relationships.
The book of Ruth is the story of a sinful lost family who is falling away from the one true God who shows mercy and grace and brings them back from oblivion and condemnation to the honour of being a direct ancestor of Christ. Just as Solomon had to "eat crow" in writing the book of Song of Solomon wherein he gets dumped by the hottie Shunamite for a shepherd boy, so too the story of pure monogamous love between Ruth and Boaz his grandfather, stands in sharp contrast to his polytheism. It may surprise the reader to learn that the average age when children were born to parents was 87 years.
2., Boaz was the father of Obed by Ruth, and Obed the father of Jesse. David was the father of Solomon by Bathsheba who had been the wife of Uriah." (Matthew 1:5-6) b.
We know Naomi returned to Bethlehem when the famine was over, because Israel had repented and Eglon was killed by Ehud.
Alas, as tempting as it can be — for both women and men — to read Ruth in that way, it is simply incorrect to do so.
In seeking to apply Scripture to our lives, it's obviously hugely important that we correctly consider the genre, context and authorial intent of the book or passage we're reading.
Why call me Naomi, when the Lord has afflicted me and the Almighty has brought calamity upon me? Have I not charged the young men not to molest you?