Jake, a little attitude adjustment would be appreciated. The whole "nice guys finish last" shtick is getting a tad old. This also includes phrases such as "I've been on so many first dates," "I don't know how many times I've been told I'm too perfect," and "I'm soooo unlucky in love." This last phrase is what I want to focus on.
I think there's a big difference between saying you are unlucky in love, and your story being unfinished. Maybe he's had some bad breaks along the way, I don't really know, but just being single doesn't mean you are unlucky.
Some high school sweethearts are firsts, onlys, and forevers; that's a great story. Some have peaks and valleys (maybe even trenches) before getting their broken roads blessed (can't get enough of that song).
Those stories are just as cool. Your story is special however it plays out.
Finally and furthermore, I'm going back to the high school sweetheart thing. We all may not be 18 anymore, but that doesn't mean that there isn't someone out there for us who IS. Don't give up hope.
(That ending's what I call a curveball.)
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