Shivangi Sinha
Ashley Hills met Aubrey Trail and Bailey Boswell through a dating app. It was not until November 2017 that the police contacted her and asked her to come in for an interview. At the time, investigators were looking into the disappearance of Sydney Loofe, who had gone missing after meeting the same pair through a dating app. Ashley’s revelations about her experiences with Trail and Boswell helped investigators with the case, which ultimately led to their arrests in connection with Loofe’s murder. Hulu’s ‘Swipe Right on the Devil’ gives Ashley a platform to share her story, reflect on her experiences with the pair, and speak openly about her time with them.
Ashley Hills Became a Part of a Relationship With Aubrey Trail and Bailey Boswell
Ashley Hills shared that she had always been someone who craved love and attention from others and openly spoke about her insecurities. She also recounted experiencing alleged abuse at the hands of her stepfather from the age of 10. At 20, she decided to put herself out there and explore dating. She joined Tinder in 2017, where she met a woman who introduced herself as Jenna. Ashley later learned that Jenna was actually Bailey Boswell. As they began talking, Ashley said that Bailey told her about having a “sugar daddy” who took care of her financially.
Ashley went to Wilber, Nebraska, to meet Bailey Boswell and Aubrey Trail. She shared that Trail would often show her pictures of other women who were allegedly part of their group and had similar “sugar daddy” arrangements with him. Ashley said that she eventually entered into a similar relationship with Trail. According to her, in exchange for money, she was expected to spend a day each week at the apartment in Wilber and follow the house rules. She said in the episode that Aubrey allegedly paid her bills, gave her gifts and money. She stated that he also took her, Bailey, and another woman on an all-expenses-paid trip to Branson, Missouri.
During the summer of 2017, Ashley said that Aubrey told her he allegedly had a coven of 12 witches and that she could become the 13th member. However, she added that he allegedly claimed that she would have to take a life to gain her powers. She said that is when she started imagining their person to be her stepfather, and it started feeling like a thing she could possibly do. Ashley shared that Bailey claimed to be a witch with healing powers, while Trail allegedly described himself as a vampire who could fly. Ashley also later testified that Bailey had allegedly spoken about wanting to “pour acid into someone” and burn them.
Ashley Hills’ Testimony Proved Quite Powerful for the Prosecution
Ashley Hills was contacted by investigators after Sydney Loofe went missing. In a recorded interview featured in the episode, she initially said she would not reveal anything because she believed Aubrey Trail and Bailey Boswell could hear them from the room, given their alleged supernatural powers. She eventually described her experiences with the pair. Ashley added that, in the summer of 2017, she had been at a TJ Maxx while planning a trip to Pennsylvania when she suffered a panic attack. She said she had decided to end the arrangement and told Bailey she was done. Ashley maintained that she had not been in contact with either of them since then.
During her testimony, Ashley said she believed Trail could read her mind and admitted that she believed everything he told her, adding that she was “scared.” She also described Bailey’s supposed reaction when they allegedly spoke about torture and killing. Prosecutors later highlighted Ashley’s testimony that Bailey’s “eyes lit up” when discussing these alleged acts. She further testified that Trail had allegedly whipped and choked her with a belt. Her testimony helped prosecutors build their case against both of them. Both were ultimately convicted in connection with Sydney Loofe’s murder, bringing a measure of justice for Loofe and her family.
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