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1* In one of the earlier strips, Nate being dumped by his first girlfriend, Angie... ''right before Valentine's day, no less.''
2** 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 Mr. Rosa and asking for some tape. A pretty painful gutpunch, to say the least.
3* Nate's HeroicBSOD after learning Artur let him win in a chess game he beat him in.
4* In a 2013 arc, [[spoiler: Jenny reveals that she's moving.]] One strip has one of the most heartbreaking exchanges ''ever:''
5-->[[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%. ''(walks away)'' Then yesterday she said it was 100%. ''(SNIFF)''
6-->'''Nate''': 100% never sounded so bad.
7* When Nate got a new girlfriend named Trudy, these moments mixed with SugarWiki/HeartwarmingMoments would show up, specifically in this [[http://www.gocomics.com/bignate/2015/12/06 strip.]]
8** Another strip has Nate find out that Trudy is a seventh-grader while Nate is only a sixth-grader. It's heartwrenching to see Nate so despondent, thinking that Trudy would never hang out with a sixth-grader.
9-->'''Nate:''' Ha! Some dream girl Trudy turned out †o be! The minute she finds out I'm in sixth grade, she BAILS! I guess I'm not MATURE enough for her! I guess I'm just a little KID!
10-->''({{beat panel}})''
11-->'''Nate:''' ''(utterly heartbroken)'' I guess I'll go home and cry into my blankie.
12* 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]]"
13* One summer strip begins with Nate complaining about Mrs. Godfrey putting Nate in a difficult situation in summer school, followed with two panels of Marty berating Nate and [[TheReasonYouSuckSpeech explaining why the predicament he's in is his fault, and his alone.]] The strip then ends with Nate lying in bed with [[HeroicBSOD 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.
14** Doubly depressing when compared to all the times Nate getting in trouble has been PlayedForLaughs.
15* In one of the novels, Nate's messy locker appears to have caused Francis to lose a very valuable and important video camera the school lent him, landing Francis in ''massive'' trouble. The ensuing fight culminates in Nate revealing Francis's EmbarrassingMiddleName to the whole school, prompting Francis to end their friendship. A distraught Nate [[HypnoFool has a hypnotist hypnotize him to be neat]] and at first, this seems to pay off, with all of Nate's teachers gushing over his homework looking so perfect but things quickly go sour when Nate's new neatness causes him to waste the time his father gives him for drawing before bed getting the lines for his comic panels just perfectly straight and then prevents him from being able to eat his TrademarkFavoriteFood. To top it all off, even cleaning up the locker completely doesn't turn up the camera so between that and Nate humiliating him, Francis still wants nothing to do with Nate, who is clearly utterly miserable.
16* [[https://www.gocomics.com/bignate/2024/03/11 This strip in March 2024]] kickstarted a month-long arc when Daphne, Nate's current girlfriend, is told and practically gaslighted by her friends into thinking she and Nate should break up because everyone in their school is expecting them to break up already and they might as well get it over with. What follows for the next two weeks is a sad and nail-biting storyline when Nate, after being informed by Randy, starts to believe that Daphne is going to break up with him, causing him to become depressed and heartbroken. He even tries to approach Daphne herself to ask her if she wants to break up, after Teddy told him he should try to get it over with as soon as possible.
17** Nate's reaction in [[https://www.gocomics.com/bignate/2024/03/18 this strip]] is particularly heartwrenching. You can practically see him reliving the memory of Angie's breakup all over again.
18** Readers were especially tense and anxious during this arc due to the slow and gradual buildup. Many were freaking out in the comments about how they don't want Nate and Daphne to break up, due to being his healthiest and cutest relationship, while others assumed a ForegoneConclusion that it would end in them breaking up due to cynicism in thinking Peirce wouldn't keep them going for longer than a year, given the track record of Nate's past relationships. It's honestly sad to see how much of a CosmicPlaything Nate has become that many already believe he's bound to fail. You'd want to hug the poor kid.
19** Ultimately, the end of the arc turns around into one of the most SugarWiki/HeartwarmingMoments in recent years after Nate and Daphne talk it out and realize they don't want to break up with one another, [[https://www.gocomics.com/bignate/2024/03/28 reaffirming their love for each other]].

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