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|Full Name:||Ashley May|
|Alias||Jesse's New Girlfriend|
|Family:||Shelly May (Mother)|
|First appearance:||Psycho Family Disney Trip|
Ashley May 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 Girlfriend was.