Ashley May .

{Construction}} Ashley May is Jesse Ridgway's girlfriend who was a recurring character of the fourth season of THE DEVIL INSIDE SERIES.

History
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 previous girlfriend was. It is implied she broke up with Jesse because she was getting tired of Jesse’s focus on both the videos and StoryFire, specifically what Jesse dubbed the “big marketing push”. When Jesse was trying to reconcile with Ashley at first, her dad in particular manhandled him, yelled at him, then kicked him out of their house.

Just a month after the break up, she 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 Nick who gave her the address to Jesse's new home. Ashley then barged into Jesse's home where they got into a fiesty row which resulted in his Xbox Series X and his $10,000 TV being destroyed.

In, "I Lost the Girl of My Dreams", some days later, Ashley came over to Jesse's house to talk with him. Since she was filming with Jesse's camera, he took it back. They engaged in a sentimental conversation where arguments were had. They both jumped into the hot tub despite Ashley not wanting to at first. They continued their dramatic and sentimental conversation/argument over at the lake then later hugging eachother. Shortly after, she moves into his lake house. It is unknown if the events of the breakup then reconciliation were real or staged as part of a series.