* 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 HeroicBSOD after learning Artur let him win in a chess game he beat him in.
* In a 2013 arc, [[spoiler: Jenny moves.]] [[spoiler: Jenny]] breaking the news to Nate gives us one of the heartbreaking lines ''ever'':
--> [[spoiler: Jenny]]: Last month, my mom told me there was a 50% chance we'd [[spoiler: 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 CrowningMomentofHeartwarming would show up.
** [[http://www.gocomics.com/bignate/2015/12/06 "How was school?" "Great!"]]
* The third panel of [[http://www.gocomics.com/bignate/2001/12/25 this Christmas strip]]; [[MeaningfulBackgroundEvent look closely at Nate's wish list]] and you'll see that the list says: [[DepartmentOfRedundancyDepartment 1. Dog, 2. Dog, 3. Dog.]]