Prior to the music trio coming to Ponyville, Derpy had a hopeless crush Ponyville’s timekeeper, Doctor Hooves. Sweetie Drops (under the alias “Bonbon” at the time) often acted as wing girl to the pegasus, but the latter’s clumsy nature often causes the plans to backfire. As it turns out, Doctor was also interested in the klutzy mail girl the first time they crashed into each other. He’s just not great at interacting with others since he doesn’t have many friends at the time.
 
Let’s just say they finally hooked up thanks to Bonbon.
 

 
It’s been so long since I last did a DtB6 drawing. This is kinda of a continuation of the previous DtB6 picture of how the B6 became friends (in my necessary headcannon).