Sentimental Journey

Both are episodic anime covering a small number of girls with no real connections. Both of them are based of Visual Novels that also share a multitude of similarities. Both series are 12 episodes and easy to watch over long periods of time since episodes have little to nothing to do with each other. Sentimental Journey's focus changes every episode, while Diamond Dust Drops Focal Character changes every 2 episodes. 

Each arc (or episode) focus on a girl. Both adorable slice of life with individual stories. Also based on a game.  

Each episode tells a story about a girl and her dreams.  

Both of these shows focus on bittersweet slice of life type plots. Asatte no Houkou's plot is better developed, with more depth, than Sentimental Journey's though, because SJ is a series of short stories. Still, both convey a similar feeling and if you watched SJ for the slice of life setting and enjoyed the "almost but not quite romance" characters, then you might want to give Asatte no Houkou a try.