Play My Girl The Game
In My Girl (from Soda Drinker Pro and Vivian Clark creator Will Brierly) you play as Thomas J in a coming-of-age story that's... well, I'm sure you've seen the 1991 movie. In this game you are Macaulay Culkin's character. So you know what happens.
Spoiler: It's bummertime. Even the MIDI version of the song "My Girl" adds to the bummer vibe.
You can play My Girl right here.