This is a great story Greg. The twist on throwing Penny in the fountain makes this a potential Country hit. However, if you're not the performer, you need to ask yourself what male country artist would portray themself as fat and ugly? If you say "a loser" you eliminate the problem that using a physical trait creates."Some real fat books" could be "Self-improvement books".
You could also write about how much you spent to change your woeful looks instead of lipo and nose job. That way you're not being specific enough to turn off a potential performer because of a physical trait - yet establish that your looks were also an issue with women.
Your chorus is strong and easy to remember.
I suggest making the part where you talk about buying the diamond ring your bridge. However the last line there seems rather weak. "She was cuddling with another man and I became upset."may work better. Follow that with "So I snuck up behind them and..." before you finish with your last chorus. On the last chorus you end with "And I sure hoped she drowned". I think it's too mean of a line to make this lyric as fun as it could be.
You may want to rework the last line and the previous rhyme line on the last chorus.

http://www.soundclick.com/Summeoyo
http://www.ourstage.com/profile/summeoyo1