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| Ashley Hills: What Happened to the Survivor Featured in Hulu’s Swipe Right on the Devil? |
Ashley Hills became an important witness in the investigation into Sydney Loofe’s disappearance after revealing her experiences with Aubrey Trail and Bailey Boswell, the pair who had previously met Loofe through a dating app. In November 2017, investigators contacted Ashley to discuss her past interactions with them. Her account offered insight into the relationship dynamics surrounding Trail and Boswell and ultimately helped prosecutors build their case.
Hulu’s Swipe Right on the Devil revisits Ashley’s experience, giving her the opportunity to explain how an ordinary attempt to find love turned into a relationship that left her frightened and questioning what she had been told. Dating apps are supposed to make meeting people easier, but Ashley’s experience serves as a reminder that a convincing profile and a few charming messages do not tell you everything about someone.
Ashley said she had long struggled with insecurities and wanted to feel loved and valued. She also spoke about alleged abuse by her stepfather, which she said began when she was 10. By the time she reached 20, she wanted to explore relationships and give dating a proper chance. In 2017, she joined Tinder, where she connected with a woman who introduced herself as Jenna.
Ashley later discovered that the woman was Bailey Boswell. What began as an online conversation gradually developed into a connection that brought Ashley into contact with Boswell and her partner, Aubrey Trail. According to Ashley, Boswell told her about a financially supportive relationship with an older man, describing him as a sugar daddy. It was an arrangement that initially appeared to offer financial security and attention, although the situation would become considerably more complicated.
Ashley eventually travelled to Wilber, Nebraska, to meet Boswell and Trail. She recalled Trail showing her photographs of other women who were allegedly involved in similar arrangements with him. Ashley said she subsequently entered into a relationship with Trail in which he provided money, gifts and help with her bills. In return, she was expected to spend one day each week at the couple’s apartment and follow their household rules.
She also recalled an all-expenses-paid trip to Branson, Missouri, involving Trail, Boswell, herself and another woman. On the surface, the arrangement offered material benefits, but Ashley’s account suggested that money and gifts were only part of a much more troubling dynamic. Financial generosity can make an arrangement look appealing, yet it does not automatically make the people involved trustworthy. Unfortunately, real life rarely comes with the helpful warning labels that would make these situations easier to recognise.
Ashley also described increasingly unsettling conversations during the summer of 2017. She said Trail told her he had a coven of 12 witches and suggested she could become the 13th member. According to Ashley, he claimed she would need to take a life to obtain supernatural powers. She recalled beginning to imagine her stepfather as the person who might be targeted, explaining that the idea had started to feel possible at the time.
Ashley also said Boswell claimed to possess healing powers, while Trail allegedly described himself as a vampire who could fly. These accounts, as presented in the documentary, offer a glimpse into the beliefs and stories Ashley said she encountered while involved with the pair. She further testified that Boswell had spoken about wanting to pour acid on someone and burn them. Such conversations were far removed from the ordinary dating experience Ashley had initially sought, and they would later become significant when investigators began examining the couple’s activities.
The relationship eventually became something Ashley wanted to leave behind. She recalled suffering a panic attack at a TJ Maxx store while making plans for a trip to Pennsylvania during the summer of 2017. Ashley said the experience prompted her to reconsider her involvement with Trail and Boswell. She subsequently told Boswell that she was finished with the arrangement.
According to her account, she had no further contact with either of them after ending the relationship. Looking back, this decision marked an important turning point in her story. Ashley had entered the situation hoping to find affection and financial stability, but she ultimately decided that continuing was not worth the emotional strain. Sometimes, walking away is the most important decision a person can make, even when they do not yet understand everything that has happened around them.
Ashley’s experiences became particularly significant after Sydney Loofe disappeared in November 2017. Loofe, a young woman from Nebraska, had met Boswell through Tinder before disappearing after a date. Investigators contacted Ashley because of her previous connection with the same pair. During an interview featured in Swipe Right on the Devil, Ashley initially appeared reluctant to share what she knew.
She explained that she feared Trail and Boswell might somehow be able to hear the conversation from another room because of the supernatural abilities she believed they possessed. Her response illustrated how strongly she had come to believe some of the claims made during her relationship with them. She eventually spoke to investigators about what she had experienced, providing information that helped them better understand the pair and their behaviour.
When Ashley later testified, she described the fear she had felt while involved with Trail and Boswell. She said she believed Trail could read her mind and admitted that she had trusted what he told her. Her account also included allegations that Trail had whipped and choked her with a belt. These were serious claims presented as part of her testimony, and they helped prosecutors establish a fuller picture of her experiences with him.
Ashley also discussed conversations about torture and killing, recalling Boswell’s apparent enthusiasm when such subjects arose. Prosecutors highlighted her testimony that Boswell’s eyes had lit up during discussions of these acts. Although a witness’s account is only one part of a criminal case, Ashley’s evidence gave the prosecution additional context about the relationship between the two defendants and the behaviour she said she had witnessed.
The investigation into Loofe’s disappearance ultimately led to the arrests and convictions of Trail and Boswell in connection with her murder. Their criminal proceedings brought Ashley’s experiences into the wider public record, although her story remained distinct from the devastating loss suffered by Loofe and her family. Ashley’s testimony helped prosecutors present evidence about the defendants, but it should not be treated as the sole reason for their convictions.
The case involved a wider body of evidence considered through the legal process. For Loofe’s family, the outcome represented an important step towards accountability after an immensely difficult period. For Ashley, speaking publicly about her past meant revisiting a relationship she had tried to leave behind. Her experience also demonstrated why investigators may seek out people who previously knew suspects, even when those relationships appeared to have ended months earlier.
As for what happened to Ashley Hills after the case, publicly available information presented in the documentary offers limited detail about her current life. Her story is revisited through Hulu’s Swipe Right on the Devil, which allows her to reflect on her experiences and explain how they became relevant to the investigation. There is not enough verified information to make confident claims about her present whereabouts, career or personal relationships.
It is therefore important to distinguish what is established about her past from speculation about what she is doing today. Ashley is remembered in connection with the case because she came forward and shared her account, rather than because she sought public attention for its own sake. Her appearance in the documentary gives viewers a chance to hear her perspective, but it does not mean every detail of her private life is now public knowledge.
Opinion: Ashley Hills’ story shows why listening to survivors matters
Ashley’s story is one of the most striking parts of Swipe Right on the Devil because it shows how a relationship can become difficult to understand while someone is still living through it. Her desire for affection and financial stability was hardly unusual, and that is precisely what makes her experience worth examining. It is easy to sit comfortably on a sofa and wonder why someone trusted a person who later appeared threatening, but hindsight has a rather unfair advantage. People do not always recognise warning signs immediately, particularly when affection, financial support and fear become tangled together.
Ashley’s testimony also demonstrates why investigators should take previous relationships seriously when searching for answers. Her account did not replace the wider evidence in the Loofe case, but it helped provide context that might otherwise have remained missing. The documentary is most effective when it allows Ashley to speak for herself without turning her experience into cheap entertainment. Her story deserves attention, not judgement.
Ultimately, Ashley Hills’ experience remains an important part of the wider story surrounding Sydney Loofe’s disappearance and the investigation that followed. Her decision to speak to investigators helped bring forward information about Trail and Boswell, while her testimony gave prosecutors further insight into their alleged behaviour. Swipe Right on the Devil also raises broader questions about trust, online dating and the difficulty of recognising an unhealthy relationship before it becomes overwhelming.
There is no need to assume that every online connection hides a sinister story, but a little caution is hardly a bad idea. Ashley’s account is a reminder that people deserve to have their experiences heard without being blamed for the choices others made. What stands out most to you about her story: her decision to walk away, her willingness to testify, or the role her account played in the investigation? Share your thoughts and join the conversation.