There are a number of ways Poor Boy can be hurt in this game. The most common ways are being struck by those he tries to kiss or by not sneaking by Underground Residents (or Mr. Cheapot's dog) while they are angry. Another common hazard is the Poopie which can be found throughout the game while scavenging for useful junk.
- Encountering Dr. Dandy at night may prompt him to take your blood, causing 20 points of damage.
- In the path leading between District 1 and District 3 of Long Life Town, occasionally the fortune teller will stop you. A fortune of "Very good" will restore 11 hearts. A fortune of "Very bad" will cause 11 points of damage.
- In 9 Long Life Town, there is a spot where you can jump down. This will cause 16 points of damage.
- In Undasura Park, there is a slide that causes 3 points of damage when used and a set of swings that can do the same. But every other time you use the swings, they will restore 3 hearts. A spinning globe-like jungle gym will dizzy Poor Boy, causing him 12 points of damage.
- Failing to sneak by Leo out of the bathhouse will cause 2 points of damage. Taking a bath "incorrectly" will cause Leo to yell, causing 2 points of damage. Soaking in the bath for too long will cause 4 points of damage.
- Acknowledging the Invisible Man in Scarecrow Field will prompt him to attack you.
- Ringing the giant bell in Worldly Desire Temple while Monk's daughter is awake will cause 3 points of damage.
- Telling Bell that you are "Nobody" will prompt her to attack you, dealing 3 points of damage.
- Drinking Miss Zombie Mika's tea the first time will cause 23 points of damage. 44 points for the second and 59 points for the third.
- In the cemetery past midnight, a reaper will appear who will take damage in multiples of 4 starting at 4.
- Eating Frogs and Dead Cicadas will cause 1 point of damage
- Eating Wilting Flower will cause 4 points of damage
- Eating Funny Cola will cause 6 points of damage
- Eating the Heart Breaker medicine will cause 4 points of damage
- Eating a Cluster Mamaryllis will cause 12 points of damage
- Reading a comic at a bench risks 4 points of damage if the comic is boring.**
- Using Tobacco reduces you to 1 Heart Point.*
Note: * If you are already at 1 Heart Point, you will become Heartbroken and the game will end.
Note: ** Poor Boy will tear up the comic if it is "the worst."
While not hazards, Drinking Fountains can each only be used once until you sleep again.
- Undasura Park +3 Hearts
- Worldly Desire Temple +8 Hearts
- Scarecrow Field +12 Hearts
- Funny Bone City +16 Hearts