My Hot Date (and other embarrassments) by Noah Van Sciver
Since it's initial publication in 2015, My Hot Date has becoming something of a modern classic. It's a coming-of-age story, told by one of this generation's best story-tellers.
This autobiographical story is set in Phoenix, AZ in the late 1990s. A young Noah Van Sciver is a poor skater kid, trying to figure out what it means to "become a man." He meets a young woman in an AOL chat room sets up a "hot date" with her at a local mall.
This story is hilarious, sweet, and sad, and perfectly captures those moments of self realization, where we can often feel so far internally from how we project externally.
This expanded edition comes with the story's 20 page follow-up story, "Holly Hill."