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the first song, im in love with an egirl, follows the main character "lonely boy" who has an infatuation with a female twitch streamer, and believes that dating her will solve all of his mental health problems.
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the second song, internet ruined me, continues this pattern of lonely boy harrassing the streamer. it also further establishes him as an incel.
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your new boyfriend is the third song of the trilogy, and it was also the most popular. after it was released it quickly became extremely popular, placing on several UK streaming charts. this song also introduces the twitch streamers new boyfriend, jared.
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finally, his newest song is called soft boy. im not totally sure if this is an official part of the trilogy (four...logy?) but its here nonetheless. this one is about a "soft boy" or a guy who shows his soft side to girls in an attempt to get with them. also it took forever to come out!!! over a year since wilbur first showed off the song.