This kind of revision experience can be so frustrating. Revisit the tried and true: take a break from it. Maybe you’ve already done that—sixty times. Try it a sixty-first time and this time put it out of your mind entirely. Forget about it. Really. You’ve been working on it for six months. What happens if you step away from it for six months? Some stories demand a more significant break. It can feel a bit like giving up, but that’s not what’s happening. When you do return to it, you and your state of mind will be different enough that the next revision may be the one that brings things in line.
When all else fails, shake up the story as much as possible in an effort to really see it anew. Ask a series of “what if?” questions that knock the story on its head. Look at those elements you’ve taken for granted. That father and son? What if they’re not related at all, but really unlikely friends? The ending where she accepts his proposal? What happens if she doesn’t? Or if she proposes instead? Or if he proposes something entirely different than marriage, such as an open relationship, an abandonment of the stable life they’ve set up, or a trip to the Ozarks. Not much will come out of most of the questions you pose, but the process may make you think about the story so differently that you do stumble upon the question that helps everything fall into place.
Here are a few other ways to shake up the story:
Change point of view strategy. If you used first, revise in third from a different character’s perspective. Do this for the whole story or for just a problematic scene.
Rewrite so that the current ending is the story’s beginning.
Choose a few key actions. Have the character do the opposite.
Again, these revisions likely won’t end up in the finished story. Instead, they encourage you to approach the story fresh. What changes? What new possibilities emerge? In going through this process, you’ll learn more about your characters and the story and, hopefully, find yourself headed in a direction that works.