The Truth About The Dating App Killer

On November 15, 2017, Sydney Loofe readied herself for her second date with a woman named Aubrey she'd met on Tinder (via the Omaha World-Herald). After their first date, Loofe texted her friend about the "super cute girl" she'd just hung out with but later told her friend (per News Channel Nebraska) she'd be cautious and "take her with a grain of salt." Twenty-four-year-old Loofe lived in Lincoln, Nebraska, and worked as a cashier at Menards, a hardware store. Her family remembers her as a kind person who loved the outdoors and had a passion for animals. She spent her free time golfing, fishing, and caring for her cat, Mimzy (via Snider Memorial).

Little did Loofe know that her date Aubrey didn't exist. The woman she called Aubrey was Bailey Boswell. More disturbingly, Boswell and her boyfriend, Aubrey Trail, had purchased bleach, saws, and trash bags earlier that day. Later, the couple would use those tools to dismember Loofe's body (per KETV and Omaha World-Herald). That evening, Loofe's friend offered her more hours at their job, but Loofe declined, citing the upcoming date with "Aubrey." As reported by BBC, she posted a photo to Snapchat with the caption, "Ready for my date." Twenty-four minutes after her phone pinged outside Wilbur, Nebraska, it went silent (per News Channel Nebraska). Nearly a month later, authorities found Loofe's remains, chopped up in 14 pieces and scattered along a gravel road about 90 miles outside of Lincoln (per The Independent).

Over the next few years, the story of Sydney Loofe's murder spiraled into bizarre headlines about witches, sex cults, and antique fraud. After Aubrey Trail admitted to killing Loofe, newspapers dubbed him "The Dating App Killer." According to KSNB, he and Bailey Boswell used Tinder to lure several women into his "group." The sensational details about Loofe's murderers seem cherry-picked from pop culture's fascination with true crime. The story includes grifters, master manipulators, and the occult. Unfortunately, the shocking nature of the story overshadows Loofe's more familiar but no less exceptional story — a Nebraska woman looking for love whose life was needlessly cut short.

Trail has a long career of check fraud, theft, and traffic violations dating back to 1999, spanning states across the midwest and east coast (via Heavy). His main con involved writing bad checks in exchange for antiques such as rare coins or silver. An antique dealer in Iowa remembers that Trail visited her store several times and gained her trust before making a large purchase. She called him a "conman extraordinaire" and an expert liar (per KMTV). At the time of Loofe's murder, Trail and his girlfriend, Bailey Boswell, were under court order to pay $400,000 for a con involving rare coins in Kansas (via the Associated Press). Trail's penchant for manipulation extended into his romantic life, too — he used cult-like tactics on women, roping them into a tightly controlled lifestyle. His former group members recall talk of witchcraft, torture, and murder (per KFAB).

Just like Sydney Loofe, Ashley Hills met Bailey Boswell on Tinder. At the time, Boswell went by the online alias, Jenna. Boswell told Hills about an arrangement she had with Aubrey Trail. Notably, he paid Boswell to follow a specific set of "rules." The couple invited Hills to join them (via KFAB). Calling himself a "sugar daddy" and a "vampire," Trail showed Hills photos of women on his phone, some naked, calling them his witches. He explained that to become a witch and receive 200 dollars a week with other paid expenses, Hills would have to follow his rules. The agreement included contacting him every three hours, not talking to other men, and calling him "daddy" (per Inside Edition).

Hills admitted she "liked the idea of being taken care of" and agreed (via KFAB). The couple told Hills that Boswell was a magic healer and Trail could fly and read minds; Hills believed them. They said that to become Trail's thirteenth witch, Hills had "to breathe in someone's last breath," meaning she had to kill someone (via Inside Edition). Not only that, but they had a victim in mind, and they had a plan. Hills said the couple wanted her to murder Anastasia Golyakova, another woman in Trail's group. Hills got as far as shopping for an antiquing trip, during which they planned to kill Golyakova, but she ended her arrangement with Trail and Boswell.

The murder that Aubrey Trail and Bailey Boswell told Ashley Hills to commit had chilling similarities to Sydney Loofe's murder. Their plan included a rural location, a dismembered body dumped along a road, sauna suits, and death by strangulation (per KFAB and KLKN). In the year of Loofe's murder, Boswell and Trail had roped at least two other women into their witch and magic-infused manipulation scheme that often included homicidal ideation. Boswell's defense attorney later said Trail had roped in at least six other women into his group (via KNOP).

Boswell's family testified in her sentencing trial that she, too, was a victim of Trail's manipulation. As reported by KNOP, Boswell's mother, Priscilla, described her as "a normal kid, she didn't get into trouble." Even though her biological father was murdered soon after she was born, her early life looked hopeful. Dedicated to basketball, she earned a college scholarship. But while at college, a man sexually assaulted Bailey, according to Priscilla, and she then became entangled in an abusive relationship with him. The man began to traffic Bailey for sex and fathered her child. Bailey eventually left the relationship, and the child's custody was turned over to Bailey's parents. Even so, Pricilla says she was forever changed (per KNOP): "She had no self-esteem ... She was just different. She didn't have a drive, or motivation." Bailey's attorney argued that her history of abuse made her the "perfect victim" for Trail (via KNOP).

Aubrey Trail met Bailey Boswell through Backpage, an online advertising website known for its sex work listings (via KNOP and Newsweek). The prosecuting attorney in Boswell's case argued that she reached out to Trail looking for a "sugar daddy" and suggested that she got exactly what she wanted in Trail. In contrast, Boswell's family argues that she fell victim to Trail's predatory tactics, citing how he controlled her. Bailey's stepfather Jeffery Boswell remembers (per KNOP), "It was like he was looking at her saying if you do or say the wrong thing you're going to get it; he was intimidating her."

Boswell started taking part in Trail's financial cons and also aided him in luring other women into his so-called "sugar daddy" arrangements (via the Associated Press). One of the women involved with the couple, Ashley Hills, testified that the pair often fantasized about torturing and killing people. As reported by KFAB, she described Boswell as "joyful," saying, "She would smile and giggle, and her eyes would light up." Hills remembers them showing her a "kill kit" full of supplies needed to murder someone and dispose of a body. The couple even took Hills to a Walmart to pick out a victim, but she backed out (per KFAB).

The complete and accurate details of what happened to Sydney Loofe on the night of her death remain unknown. However, testimony from other women involved with the couple points to the pair fantasizing about murdering someone for months (via KFAB). Furthermore, day of the murder, Bailey Boswell and Aubrey Trail bought supplies later used to dispose of Loofe's body (per News Channel Nebraska).

Trail admitted to murdering Loofe at his sentencing trial but insisted that the murder was not planned (via People). According to Trail, when he proposed his standard arrangement, trading money for a set of predetermined rules to follow, Loofe refused. "I lured her there to try and pull her into our group. But once I sat Sydney down and explained to her our criminal activities and group sex, I knew I had made a big mistake," he said (per KSNB).

According to Associated Press (via KETV), he admitted to strangling her with an electrical cord, claiming that "Sydney did nothing but threaten to expose my lifestyle, and I killed her for it". However, in the same statement, he admitted to a habit of lying, stating (per KSNB), "Almost everything I've said before was a lie unless it benefitted me." Earlier in the investigation, he changed his story several times and bragged about drinking Loofe's blood (via the Des Moines Register).

A few days after Sydney Loofe's disappearance, Aubrey Trail and Bailey Boswell's landlord reported their apartment smelling strongly of bleach (per 10/11 Now). Authorities quickly identified the pair as "persons of interest" (via Heavy). In response, the couple turned to social media, proclaiming their innocence. Boswell said of Loofe, "She is a sweet, amazing girl." Trail offered similar sentiments: "I wish the family the best." The video ends with the pair giving the middle finger to the police. They were arrested a few days later in Missouri.

On December 4, less than a month after her disappearance, authorities used digital evidence to find Loofe's remains (per BBC). Boswell was convicted of murder, and in 2021, she was sentenced to life in prison without parole (via Death Penalty Information Center). The judge called the couple's actions "coldly planned." Separately, a panel of judges gave Trail the death penalty, though it did not hold up (per The Independent). Trail added drama during his trial by attempting to slit his own throat in the courtroom after yelling, "I curse you all!" His injuries were not serious, and the trial resumed (via The Washington Post). After sentencing Trail, the judge concluded (per The New Zealand Herald), "Ms. Loofe was needlessly mutilated by Trail in order to satisfy his intellectual and sexual curiosity."

While Trail and Boswell faced the consequences of murdering Loofe, her family and friends mourn her loss. Loofe's family requested that those wishing to honor her life donate to Omaha's Henry Doorly Zoo and Aquarium (via Snider Memorial).