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|Full Name:||Ashley May|
|Family:||Shelly May (mother)|
Wayne May (father)
|First appearance:||Psycho Family Disney Trip|
Ashley is a college student whom Jesse befriended online. After talking with each other from time to time, she and Jesse decide to date each other, and she becomes his new girlfriend. She made her debut in I Met the Girl of My Dreams At Disney World, the first in a series of "I Met the Girl of My Dreams at [insert location here]" videos. She has since made many appearances throughout Jesse's videos and other social media platforms, as she is not as shy as Jesse's previous girlfriend was. On October 24, 2020, Jesse reveals that he and Ashley have broken up because she was getting tired of Jesse caring for himself since he is always concentrating on his YouTube job, making stories on StoryFire and playing video games instead of hanging out with her, specifically what Jesse dubbed the “big marketing push”. When Jesse was later trying to reconcile with Ashley at first, her father, Wayne, forbids him from seeing her before manhandling Jesse and kicking him out.
Just a month after the break up, Ashley was trying to find Jesse after finding out from his brother that he was residing in his new lake house. This was because according to her "she wanted to work thing out with him". However, that can be considered controversial. Soon afterwards, she visited Jesse's cameraman Nick, who gave her the address to Jesse's new home. Ashley then broke into Jesse's home, where the two have a falling out because Ashley mistakenly thought Jesse was hanging out with another girl (although it turned out that he was actually hanging out with Nick), eventually leading to her destroying Jesse's Xbox Series X and $10,000 TV, causing an enraged Jesse to kick her out and nearly damaging his relationship with Ashley.
Some days later, Ashley came over to Jesse's house to talk with him and patch things up. Since she was filming with his camera, he however took it back. They engaged in a sentimental conversation where their arguments had. They both got into a hot tub, despite Ashley not wanting to go in at first. They continued their dramatic and sentimental conversation/argument over at the lake, but then later hugged each other. Shortly after, Ashley reconciles with Jesse and decides to move into his lake house, suggesting that Jesse needs to take a break from doing his videos and hang out with her more instead. It has been revealed that Jesse and Ashley are still together in real-life, revealing the break up series was all staged.
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