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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. In 2020, it is somehow revealed that she broke up with Jesse because she was getting tired of him doing his YouTube job and making stories on StoryFire instead of hanging out with her, specifically what Jesse dubbed the “big marketing push”. When Jesse was trying to reconcile with Ashley at first, her overprotective father in particular forbids him from seeing her before manhandling Jesse and kicking him out as a result.
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 barged into Jesse's home where it turns into a meltdown between the two, resulting in Jesse's Xbox Series X and $10,000 TV getting destroyed.
Some days later in "I Lost the Girl of My Dreams", Ashley came over to Jesse's house to talk with him. 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 should take a break from doing his videos and hang out with her more instead. It is unknown if the events of the breakup and reconciliation were real or staged as part of a series; this also goes for the events of all previously mentioned videos, excluding the one about the breakup(?).