- 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 BSoD 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 Heartwarming Moments would show up.
- The third panel of this Christmas strip; look closely at Nate's wish list and you'll see that the list says: 1. Dog, 2. Dog, 3. Dog.
- A few strips begin with Nate complaining about Mrs. Godfrey putting Nate in a difficult situation (i.e. sending him to summer school), followed with two panels of Marty berating Nate and explaining why the predicament he's in is his fault, and his alone. The strips end with Nate working late into the night or lying in bed with a look of utter regret and hopelessness on his face, able to do nothing but think about how much he hates Mrs. Godfrey. Granted, Marty is usually correct in placing the blame on Nate, but it hits close to home for anyone who knows the feeling of making a big mistake and having to live with the irreversible consequences.
- Doubly depressing when compared to all the times Nate getting in trouble has been Played for Laughs.
Tear Jerker / Big Nate