- In one of the earlier strips, Nate being dumped by his first girlfriend... right before Valentine's day no less.
- Strip afterward continues this by having him stare at a picture of her before ripping it up in anger. He stares at the pieces dejectedly before going to the art teacher and asking for some tape. A pretty painful gutpunch to say the least.
- Nate's Heroic B.S.O.D. after learning Artur let him win in a chess game he beat him in.
- In a 2013 arc, Jenny moves. Jenny breaking the news to Nate gives us one of the heartbreaking lines ever:
Jenny: Last month, my mom told me there was a 50% chance we'd move to Seattle. Then last week, she told me it was more like 80%. Then yesterday she said it was 100%.Nate: 100% never sounded so bad.
- When Nate had a new girlfriend named Trudy, these mixed with Crowning Momentof Heartwarming would show up.