FimFiction Link - Short ID: 154342/dear-anonymous
Published: Apr '14
Dear Anonymous would've been a long slow burn romance. Instead, it's only a 5k word dead romcom.
I liked the set up for this story. There's a new dating service in Equestria where you submit a profile and you're matched anonymously with somepony else. Then, you start exchanging letters with that pony and see if it leads to something nice.
The fic does a good job establishing Twilight's state of mind going into this whole thing. She's kinda insecure, kinda thinks this is silly, but ultimately decides to try it.
And then the story died right after she gets assigned a penpal. Classy.