- Genius Bonus: In the music video for "Your New Boyfriend", when the E-Girl replies to one of Lonely Boy's e-mails, her name shows up as "Pandora Braithwaite", a character from Adrian Mole. In the book, Pandora was briefly in a relationship with the protagonist when they were teens, but broke up with him once he refused to accept that she wouldn't have sex with him. The protagonist then proceeds to send her multiple letters proclaiming his love for her, after which she threatens to contact the police and tells him to get psychiatric help.
- Heartwarming Moments: When "Your New Boyfriend" initially premiered, some of Wilbur's friends reacted to it on Philza's stream. After the premiere finished, Wilbur messaged Phil saying that he stopped watching his own premiere to watch his friends react to it.
- Nightmare Fuel: The E-Girl trilogy is a parody of a very real phenomenon. If you're a woman on the internet, ESPECIALLY with a platform, you've likely encountered at least one guy with the same mentality, and while some are harmless, others are decidedly not.
- Tear Jerker: Almost every song from "Your City Gave Me Asthma" can be counted as this.
- "Your Sister Was Right" is a straightforward song about someone realizing how toxic they were to a partner that left them. It has culminated in this fan animation about Wilbur's character in the Dream SMP, a former Wide-Eyed Idealist turned self-hating Shell-Shocked Veteran Fallen Hero who eventually dies from Suicide by Cop.
http://tvtropes.org/pmwiki/pmwiki.php/YMMV/WilburSoot
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