Sydney Loofe Murder: The Tinder Date, the Witch Cult, and the Truth Behind Swipe Right on the Devil

On November 16, 2017, a manager at a Menards in Lincoln, Nebraska, left a voicemail for 24-year-old Sydney Loofe.

She was supposed to be at work that morning.

She hadn’t shown up.

Her friends couldn’t reach her. Her family couldn’t reach her. And when police checked her apartment, her car was still in the driveway. Her purse was inside. Her cat was there.

Sydney wasn’t.

The night before, she’d sent her friends a Snapchat with three words:

“Ready for my date.”

She was going out with a woman she’d met on Tinder. They’d already been on one date, and Sydney was excited to see her again.

Her friends knew the woman as Audrey.

Except Audrey wasn’t her real name.

And Sydney wasn’t the first young woman she’d met through a dating app.

The investigation into the Sydney Loofe murder would eventually uncover fake identities, an older man with a history of fraud, several women who described being manipulated and threatened, and a supposed coven of witches.

Yes, witches.

But the more you learn about this case, the more you realize that the supernatural claims were only one part of something much more disturbing.

Hulu’s new three-part documentary, Swipe Right on the Devil, explores Sydney’s disappearance, the investigation, and the trials of Aubrey Trail and Bailey Boswell.

We’re covering the case in two episodes of This Feels Criminal, beginning with the people who refused to stop looking for Sydney and ending with the evidence that put two people in prison.

And there’s one question we kept coming back to.

When someone is being controlled by a dangerous person, how do we determine whether they’re also responsible for controlling and harming someone else?

Who Was Sydney Loofe?

Sydney Irene Loofe was born on August 21, 1993, in Broken Bow, Nebraska.

She grew up in Neligh, a small town where, as her older brother Levi put it, everybody knew everybody.

Sydney was close with her siblings, especially her younger sister MacKenzie, who was only 15 months younger.

According to her family, Sydney was a tomboy who loved basketball, followed her older brother around, and wore basketball shorts in practically any weather.

Even Nebraska winter weather.

Which tells you a little something about her personality.

After high school, Sydney told her friends and family she was attracted to women.

Her friends were supportive. Her family, as MacKenzie acknowledged in the Hulu documentary, struggled with the news at first.

Sydney eventually moved to Lincoln for a fresh start.

She found a job at Menards, beginning as a morning stocker before moving to cashier. She lived in a duplex on Colfax Avenue with her cat, Mimsey.

One of our favorite details about Sydney comes from her coworker Michael Gascon.

When Michael was new at Menards and eating lunch alone, Sydney walked up and asked if he liked fishing.

Then she invited him to go fishing after work.

That’s such a specific little glimpse of who she was. She saw someone sitting alone and decided they didn’t need to stay that way.

Her friends also described someone who wanted a meaningful romantic relationship.

Dating wasn’t always easy. Some women Sydney met seemed interested in exploring their sexuality without wanting the same kind of relationship she did.

In the documentary, a friend remembers Sydney as someone who could be surrounded by people and still feel alone.

That part is heartbreaking.

Because when Sydney matched with someone who seemed genuinely interested in her, she was excited.

She had no reason to know what was waiting for her.

Sydney Loofe’s Tinder Match With “Audrey”

In November 2017, Sydney matched with a woman on Tinder who used the name Audrey.

On November 14, they went on their first date.

And according to the messages Sydney sent her friends afterward, it went really well.

They drove around, talked, smoked marijuana, held hands, and kissed.

Sydney described Audrey as gorgeous and seemed completely smitten.

Her friend Brittney asked for a picture.

Sydney sent her one from the Tinder profile.

The photo was filtered, but it showed the woman’s face, along with the name Audrey.

The two planned another date for the following evening.

On November 15, Sydney sent her friends the Snapchat that would later become central to the investigation.

“Ready for my date.”

She never returned home.

When did Sydney Loofe go missing?

Sydney disappeared on November 15, 2017, after leaving for her second Tinder date.

The following morning, she failed to show up for her shift at Menards.

Her manager and coworkers knew that was unusual.

Friends began contacting her sister MacKenzie because Sydney wasn’t responding to calls or messages.

Her mother, Susan Loofe, contacted Lincoln police.

When investigators and Sydney’s manager checked her apartment, they found her car, purse, makeup and work vest.

Her cat was still there without extra food.

It looked like Sydney had intended to come home.

And that’s when her friends started doing some investigating of their own.

How Sydney Loofe’s Friend Brooklyn Found “Audrey” on Tinder

One of the most remarkable parts of the Sydney Loofe investigation is the role her friend Brooklyn McCrystal played.

Sydney’s friends remembered the Tinder photo she’d shared.

But they didn’t know Audrey’s real name.

The picture was filtered, and searching for someone named Audrey wasn’t getting them anywhere.

So Brooklyn made a Tinder account.

She started swiping until she found a profile that looked promising.

The main image was a quote, but when she opened the profile, there was the picture Sydney had sent her friends.

Brooklyn swiped right.

The next morning, they had matched.

Brooklyn flirted with Audrey long enough to get a phone number.

Then she handed it straight to police.

An FBI agent later praised her initiative while cautioning that people shouldn’t put themselves in danger by trying to conduct their own investigations.

That distinction matters.

Brooklyn’s actions gave police an important lead, but no one should feel obligated to confront a potentially dangerous person to help a missing friend.

Investigators called the number.

The woman on the other end acknowledged meeting Sydney but refused to provide basic identifying information.

She wouldn’t give her real name, address or date of birth.

The phone was registered under a fake name.

But investigators used the phone’s location history, hotel surveillance and identification records to establish who she was.

Audrey was Bailey Boswell.

And she was traveling with a much older man named Aubrey Trail.

The Search Leads to Wilber, Nebraska

Sydney’s phone had last connected to a cell tower near Wilber, Nebraska, a small town about 40 miles southwest of Lincoln.

Her family had no idea why she would have gone there.

They drove through the area looking for clues.

Her father even searched through tall grass in freezing weather, hoping to find her phone.

Brooklyn and other friends went door to door.

Meanwhile, investigators traced Bailey Boswell to a basement apartment in Wilber.

The lease identified the older man staying with her.

Aubrey Trail.

The landlords described tenants who paid rent in advance and said they worked in antiques.

But they also remembered something unsettling.

The day after Sydney disappeared, the house smelled strongly of bleach.

The odor was even worse downstairs.

Investigators searched the apartment on November 19.

Bailey and Aubrey were gone.

And as police looked through the belongings left behind, they began discovering evidence that Sydney might not have been the only woman in danger.

The Other Women Who Met Bailey Boswell on Tinder

The Hulu documentary spends significant time with three women who had encounters with Bailey Boswell and Aubrey Trail.

Their accounts help explain how the couple approached young women, gained their trust and introduced them to an increasingly controlling environment.

Ana Golyakova and the Woman Named “Jenna”

Investigators found a document connecting the Wilber apartment to a young woman named Ana Golyakova.

Ana was 18 when she became involved with Bailey and Aubrey.

She had moved to the United States from Russia as a child and described growing up in an environment where her sexuality wasn’t accepted.

She met someone named Jenna on Tinder.

Jenna was another identity used by Bailey Boswell.

According to Ana, Bailey took her to Olive Garden and shopping, then introduced the idea of a wealthy older man who could financially support them.

That man was Aubrey Trail.

The arrangement came with expectations involving sex and obedience.

Ana also described participating in fraud schemes involving antiques and bad checks.

She recalled watching Bailey take photographs in different wigs and outfits to create new identities.

It was a pattern investigators would hear about again.

Ashley Hills and the Supposed Coven of Witches

Ashley Hills also met a woman named Jenna through Tinder.

At first, the conversations felt normal.

They talked about sports and difficult past relationships.

Then came the offer of money and financial support.

When Ashley met Aubrey, he presented himself as a man who could provide almost anything she wanted.

But his generosity came with rules.

Ashley described being required to call him Daddy, ask permission for basic activities, avoid speaking to other men, and check in regularly.

She testified about physical punishment for breaking the rules.

Then came the supernatural claims.

Trail told Ashley he was a powerful figure and that Bailey was a witch.

Bailey was supposedly the queen of a coven.

Ashley could become its thirteenth member.

But joining required killing someone.

According to Ashley’s account, Trail claimed that taking a life would give a witch power.

The more suffering involved, the more power she would supposedly gain.

Ashley eventually left.

And investigators began recognizing a disturbing pattern.

Young women were meeting Bailey on Tinder, being introduced to Aubrey, and finding themselves in situations involving sexual coercion, threats and promises of belonging.

Katie Brandle and the Second Missing Woman

Katie Brandle’s story is one of the most unsettling parts of Swipe Right on the Devil.

Investigators found a pill bottle with her name at the Wilber apartment.

Her mother, Jennifer, was terrified when she learned the people Katie was staying with were being investigated in connection with Sydney’s disappearance.

Katie had met someone on Tinder who used the name Kelsi.

But according to the documentary, the messages that first drew Katie in weren’t written by Bailey.

They were written by Aubrey.

Katie had recently experienced a breakup and wanted to find someone she could build a life with.

The messages offered friendship, affection and financial security.

Eventually, she met Bailey and Aubrey.

Katie described Bailey as affectionate and attentive when Aubrey wasn’t around.

But she also described seeing Bailey become withdrawn and fearful around him.

When Katie suggested they leave, Bailey said she belonged to Aubrey.

After Sydney disappeared, Katie traveled with the couple.

According to her account, Aubrey threatened her and her family if she went to police.

He also told her he wanted Katie and Bailey to find someone to torture and kill.

Katie suggested Kearney, Nebraska, as a possible place to find a victim.

That admission is uncomfortable.

Katie has spoken about struggling with guilt over the things she said while she was frightened and under the couple’s influence.

And it raises one of the most difficult questions in this case.

How do we understand someone’s actions when they’re being threatened, manipulated and trying to survive?

That question would become even more important during Bailey Boswell’s trial.

The Facebook Video From Aubrey Trail and Bailey Boswell

While investigators searched for Sydney, Aubrey Trail and Bailey Boswell released a Facebook video defending themselves.

They said they’d been unfairly portrayed in the media.

Bailey acknowledged going on two dates with Sydney but claimed she had dropped her off at a friend’s house.

She denied having anything to do with Sydney’s disappearance.

Trail criticized police.

Investigators later found another video about the disappearance that hadn’t been publicly posted.

But the Facebook video also gave authorities a new lead.

According to the Hulu documentary, investigators used information connected to the livestream to narrow down where the couple might be staying.

A detail from Ashley’s earlier account helped them connect the trail to Branson, Missouri.

On November 30, 2017, police arrested Bailey and Aubrey at a motel.

Bailey had reportedly just returned from getting Krispy Kreme doughnuts.

Sydney was still missing.

How Investigators Found Sydney Loofe

After their arrests, Trail gave investigators strange and shifting statements.

He spoke about witches, sacrifices and supernatural power.

At one point, he asked to speak away from the interview-room cameras.

He whispered about witches killing and becoming more powerful.

But investigators still needed to find Sydney.

A Lincoln police analyst studied phone-location data connected to Bailey and Aubrey.

The records showed the phones traveling together after Sydney’s disappearance.

Investigators identified an area where the phones appeared to move slowly and stop repeatedly.

They sent search teams to investigate.

On December 4, 2017, Sydney’s remains were discovered along roadsides in rural Clay County, Nebraska.

An investigator recognized a tattoo on her upper arm.

It read:

“Everything will be wonderful someday.”

Sydney had gotten the tattoo from a song lyric.

Her family shared in the documentary that she’d been struggling emotionally and trying to find her footing as a young adult.

She had even talked about coming home for a while to reset.

She was making plans for herself.

She was trying to feel better.

And now her family had to face the fact that she wasn’t coming home.

Who Was Aubrey Trail?

Aubrey Trail had a lengthy history of fraud and other crimes before Sydney’s murder.

He used aliases, wrote bad checks, and became involved in scams involving antiques and coins.

In Swipe Right on the Devil, Trail discusses a childhood he describes as abusive and chaotic.

His attorney also talks about his difficult early life.

Those accounts may provide context for how Trail understood himself, but much of the childhood narrative comes from Trail, who openly acknowledges being a habitual liar.

He even describes making a living by convincing people of things that weren’t true.

That admission is important.

Because Trail offered investigators several different explanations for Sydney’s death.

He confessed to killing her.

But he kept changing the story of how and why it happened.

What Happened on the Day Sydney Loofe Was Murdered?

The evidence presented at trial painted a disturbing picture of November 15, 2017.

According to the investigation detailed in the documentary, Trail and Boswell were staying at a hotel in Lincoln that morning.

Their phones traveled to the area near Sydney’s home and workplace.

Trail entered the Menards where Sydney worked.

Investigators believed Sydney passed him without recognizing him.

He then purchased a gallon of Drano.

Afterward, Trail and Bailey went to Home Depot.

Surveillance footage showed them buying tools and supplies, including a saw, saw blades and drop cloths.

Back in Wilber, Bailey purchased additional cleaning supplies and trash bags.

Hours later, Bailey picked Sydney up for their second date.

The prosecution used these purchases, along with phone records and forensic evidence, to argue that Sydney’s death was planned.

That evidence was particularly significant because Trail had repeatedly claimed her death was an accident.

Aubrey Trail’s Changing Confessions

Trail initially told investigators and reporters that Sydney died during a consensual sexual encounter.

He claimed she had agreed to participate in a sexual fantasy and that her death was accidental.

He also claimed other women were involved.

But investigators found no evidence that Sydney had known Trail before the night she disappeared.

Her friends had never heard her mention him.

And the evidence from November 15 showed Trail and Bailey purchasing supplies before Sydney’s date.

During his trial, Trail abandoned parts of his earlier account.

He acknowledged there was no sexual fantasy and no other women in the room.

He continued trying to protect Bailey from responsibility.

But investigators uncovered evidence suggesting the two had been coordinating their stories.

Aubrey Trail’s Trial and Death Sentence

Aubrey Trail went on trial in June 2019.

His defense centered on the argument that Sydney’s death wasn’t premeditated murder.

Then he created a scene that stunned the courtroom.

On June 24, 2019, Trail shouted that Bailey was innocent and cut his own throat with a razor blade he’d concealed.

He survived.

The judge determined the trial could continue after questioning jurors about whether they could remain impartial.

On July 10, 2019, Trail was convicted of first-degree murder and conspiracy.

In June 2021, he was sentenced to death.

His conviction was later upheld on appeal.

Bailey Boswell’s Trial: Manipulated Victim or Willing Participant?

Bailey Boswell’s trial began in 2020.

Her defense argued that she had been manipulated and controlled by Aubrey Trail.

Attorneys pointed to the accounts of Ana, Ashley and Katie, who described Trail’s threats and abusive behavior.

Their argument was that Bailey had also been drawn into his world and was afraid to leave.

There was evidence supporting the idea that Trail could be controlling.

Katie described seeing Bailey behave differently when he wasn’t present.

Bailey’s mother worried that her daughter was in danger.

And Bailey herself later described feeling trapped.

But prosecutors presented evidence of Bailey’s active participation.

Witnesses testified that she recruited women through Tinder, created false identities and participated in discussions about killing.

The prosecution also introduced coded messages exchanged between Bailey and Trail while they were in custody.

Investigators found a cipher key in Bailey’s cell.

When they decoded the messages, they discovered Trail discussing how they could present the sexual-fantasy account in a way that protected Bailey.

The prosecution argued that Bailey wasn’t simply following orders.

She was helping carry out the plan.

In October 2020, Bailey was convicted of first-degree murder, conspiracy and improper disposal of human remains.

Why didn’t Bailey Boswell get the death penalty?

Bailey’s sentencing was decided by a three-judge panel.

Nebraska required all three judges to agree before imposing a death sentence.

Two voted for death.

One voted for life imprisonment.

Because the panel wasn’t unanimous, Bailey received life in prison without the possibility of parole in November 2021.

Her appeal was rejected by the Nebraska Supreme Court in May 2024.

What Did Aubrey Trail Finally Say About Sydney Loofe’s Murder?

One of the most disturbing moments in the final episode of Swipe Right on the Devil comes when Trail offers yet another explanation.

Speaking from death row, he admits that he’d lied repeatedly in an effort to protect Bailey.

He then claims that Bailey wanted to become a powerful witch and that he allowed her to kill Sydney as part of that ambition.

Trail says there was no accident.

He claims they killed Sydney because they wanted to.

He also says they had considered killing other women who knew too much about their activities.

But here’s the problem with taking that final confession at face value.

Trail had already admitted he lied about practically everything.

His last version is consistent with important parts of the prosecution’s evidence, including the advance purchases, the recruitment of women and the coded jail messages.

But the specific claim that Bailey was the driving force behind the murder is still Trail’s account.

And it comes from a man who had spent years trying to manipulate investigators, reporters and the courts.

We can take his statements seriously without assuming every detail is true.

The evidence establishes that both Trail and Bailey were convicted for their roles in Sydney’s murder.

His final explanation doesn’t change that.

Why Was Sydney Loofe Chosen?

Sydney’s sister MacKenzie asks one of the most painful questions in the documentary.

Why Sydney?

Other women had met Bailey and Aubrey.

Other women had spent time with them and heard their threats.

Why was Sydney the one who didn’t come home?

Near the end of the documentary, Trail offers an answer.

He claims they thought Sydney was someone who could disappear without attracting much attention.

But they were wrong.

Sydney’s coworkers noticed when she missed her shift.

Her friends remembered the Tinder profile.

Brooklyn found Bailey and obtained the phone number that helped investigators identify her.

Her family searched for her in freezing weather.

And everyone kept pushing for answers.

MacKenzie makes clear that Sydney was deeply loved.

She had people checking on her.

She had people who cared.

Trail’s claim about why Sydney was selected is his own account, not an independently established motive.

But the response to her disappearance is undeniable.

Sydney’s people refused to let her vanish without a trace.

Where Are Aubrey Trail and Bailey Boswell Now?

As of October 2026, Aubrey Trail remains on death row in Nebraska.

Bailey Boswell is serving life in prison without parole at the Nebraska Correctional Center for Women.

Both were convicted in connection with Sydney Loofe’s murder.

Trail’s death sentence and Bailey’s life sentence followed separate trials and sentencing proceedings.

What Is Swipe Right on the Devil on Hulu?

Swipe Right on the Devil is a three-part Hulu true crime documentary released on October 22, 2026.

The episodes follow the investigation into Sydney Loofe’s disappearance, the experiences of other women who met Bailey Boswell and Aubrey Trail, and the evidence presented during the murder trials.

The documentary also features Sydney’s family and friends, whose interviews give the case an emotional depth that court records alone can’t provide.

For our two-part This Feels Criminal coverage, we’re using the documentary as the starting point while also digging into the investigation and legal proceedings.

Episode 1 drops on Tuesday, October 27, 2026: Ready for My Date follows Sydney’s disappearance, the search, and the women who helped investigators uncover the couple’s activities.

Episode 2 drops on Thursday, October 29, 2026: Witches Can Be Made covers Trail’s changing confessions, the evidence from Sydney’s final day, the trials, and the question of Bailey’s responsibility.

Key Takeaways From the Sydney Loofe Murder Case

• Sydney Loofe disappeared on November 15, 2017, after leaving for a second Tinder date with a woman using the name Audrey.
• Audrey was actually Bailey Boswell, who was involved with Aubrey Trail.
• Sydney’s friend Brooklyn helped investigators identify Bailey by finding her Tinder profile and obtaining a phone number.
• Investigators discovered other young women who described being recruited through Tinder and subjected to threats, coercion and manipulation.
• Trail claimed to possess supernatural powers and lead a coven of witches, but the trial testimony revealed a pattern of control and abuse.
• Phone records, surveillance footage and purchases made before Sydney’s date became important evidence of planning.
• Sydney’s remains were discovered in rural Clay County, Nebraska, on December 4, 2017.
• Aubrey Trail was convicted of first-degree murder and sentenced to death.
• Bailey Boswell was convicted of first-degree murder and sentenced to life without parole.
• Trail’s final explanation for Sydney’s murder included claims about Bailey’s motives, but his history of changing stories means those claims require caution.
• Hulu’s Swipe Right on the Devil explores the case through interviews, investigative footage and the experiences of Sydney’s loved ones.

Frequently Asked Questions About Swipe Right on the Devil