Awkward Moments as Vintage Paperbacks

Pulp fiction that only makes sense if you’re a little bit awkward

Jack Shepherd
3 min readDec 4, 2021


Have you ever been stuck in an endless “I’m good. How are You?” loop? Have you ever felt like skipping the country and starting a new life because you thought someone was waving at you but they were waving at the person behind you? Have you ever literally forgotten how a smile’s supposed to work and ended up just kind of baring your teeth at someone like an angry cat? Here are 9 truly chilling problems for the socially awkward, helpfully illustrated by vintage paperbacks.

The Chilling Horror

A pulse-pounding tale about a normal interaction gone horribly, irrevocably wrong.

Signet Books/Jack Shepherd

The Ghastly Thriller

A terrible mistake that turns into an endless waking nightmare.

Ace Books/Jack Shepherd

The Story of a Dark Past

A haunting reminder that we can never outrun our past.

Gold Medal Books/Jack Shepherd

The Gritty Crime Novel

The macabre true story of a villain so odious, you won’t believe it happened!

Avon Books/Jack Shepherd

The Heartbreaking Tragedy

A tear-jerking melodrama about the birth and death of something beautiful.

Dell Books/Jack Shepherd

The Noir

A vile criminal act. A life in ruins.

Private Detective Stories/Jack Shepherd

The Urban Realism



Jack Shepherd

I have a newsletter about crossword puzzles and a podcast about rom-coms. Formerly editorial director @BuzzFeed. Email: JackAShepherd at gmail