10 Video Game Enemies You Felt REALLY Bad For Killing

3. Jen - Prey (2006)

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Human Head Studios

The original 2006 Prey may not be a great game, but it does nevertheless boast one of the most memorably upsetting boss fights of the last two decades.

Protagonist Tommy spends the early chunk of the game seeking out his girlfriend Jen, who like him has been abducted by aliens. But things take a tragic turn when he finally finds her, only to discover that her body has been fused with that of an alien creature.

A boss fight ensues in which Tommy is forced to destroy the monster and in turn mortally wound Jen. At the end of the battle, a dying Jen begs the player to kill her, which they have to do in order to continue.

The only small solace, however, is that the game makes it incredibly clear the afterlife is a concept in this world, and at the end Jen is seen together with Tommy's grandpa in the afterlife. Phew.

So, as horrifying an outcome as Jen's death was, at least she became more than just worm food.

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Stay at home dad who spends as much time teaching his kids the merits of Martin Scorsese as possible (against the missus' wishes). General video game, TV and film nut. Occasional sports fan. Full time loon.