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Chapter 1: Who was Sydney Loof and what happened on her second date?
24-year-old Sydney Loof thought she was going on a second date with a woman that she'd really hit it off with. She got ready, she put on her outfit, snapped a selfie captioned, ready for my date. A date that she would never return home from.
As the days went by, her best friend became the unofficial lead detective on this case, going undercover on Tinder to find the exact person that had lured her best friend on a date. And it quickly became clear this person wasn't real. The profile was fake. And in the hours before they'd met up with Sydney, this person had been all over town buying saws, bin bags and bleach.
Hello, and welcome to Outlaw Podcast. I'm Eleanor Neal, and in today's episode, we're in Nebraska in 2017, where the disappearance of 24-year-old Sydney Loof would begin with one simple question. Who was the last person to see her? And at first, that question seemed answerable. There were messages. There was a name. There was a profile. There was a final plan Sydney had made before she vanished.
Chapter 2: What were the initial reactions and actions taken after Sydney went missing?
But every time investigators found what looked like an answer, it only led them deeper into something else. Because the person Sydney thought she was meeting up with that day wasn't who they said they were. And they wouldn't be alone, either.
In case you didn't already know, this month is Pride Month, and throughout the month of June here on Outlaw Podcast, we're centring LGBTQ plus cases that need to be spoken about. And Sydney's case really struck a chord with me, I think because it speaks to a very modern problem for many queer folks. We all want to find love.
but for LGBT people, especially those living in more rural areas, the dating pool is very small and hard to find actually. It can feel like online dating and dating apps are the only realistic way to meet someone. But unfortunately with that reliance on technology comes a very real vulnerability because when you're dating online, people can pretend to be anything, anyone they want.
They can lie easier, they can manipulate easier. In queer spaces, there are often fake profiles, there's catfishes, there's scammers, people waiting to collect explicit photos and then blackmail people in return. It's the Wild West out there, at best, and at worst, it can lead to cases like this one.
And that's what makes Sydney's case so devastating because Sydney wasn't looking for danger or drama. She was simply looking for love and connection.
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Chapter 3: How did Sydney's best friend investigate her disappearance?
But someone chose to exploit that. Now, before we get into it, I want to give my usual disclaimer that I mean absolutely no harm or disrespect to anyone that we talk about in today's case. This episode has been made with the utmost care to not only honour and memorialise those who lost their lives but also to recognise the profound grief their loved ones continue to endure.
And given the nature of today's episode, we'll be covering some very sensitive topics, including murder, dismemberment, coercion, sexual themes, mental health struggles, and LGBTQ vulnerability and targeting. This episode is created with the hope to raise awareness, to inspire change, and to further victim support. Viewer discretion is advised. Now it's time to get into today's case.
Before Sydney's name was attached to headlines and court documents and crime scene evidence, she was just Sydney. A loved daughter, a middle sibling, a loyal friend, someone who cared deeply about other people, and someone who was still trying to work out exactly where life might take her. So before this story becomes about what happened to her, It needs to be about who she was.
Sydney Irene Loof was born on August 21st 1993 in Nebraska. She was the second child to parents Susie and George. She had an older brother named Levi and soon a younger sister named Mackenzie and they all lived together in a tiny village where Sydney would grow up for the first seven years of her life. They were a pretty religious family, so Sydney spent a lot of time going to church as a child.
But when she wasn't at church services, you could find Sydney on some sort of adventure. She was a very outdoorsy girl, she loved to get out in nature and get mucking about, you know? Her family would go on fishing vacations and Sydney became really blooming good at it. She was up for trying anything and everything. Any sport, she was a very sporty girl.
She was on her school's basketball team, she loved golf, she loved bike riding. But at some point during her teenage years, Sydney was diagnosed with scoliosis, which really hindered her ability to engage in the sports that she loved so much.
If you're unfamiliar, scoliosis is a medical condition where a person's spine curves sideways, forming either like a C-shape or an S-shape, and this affects people in different ways depending on their severity. Most people with scoliosis can live healthy, active lives. Sometimes surgery is needed, and sometimes it does sadly stop people from living the active lifestyle that they're used to.
And when this happened to Sydney, it really affected her. Of course, physically, but emotionally too. It must be awful being told that you actually can't play the sports that you love because your body isn't able to sustain that kind of pressure anymore. You're used to the regular endorphin release getting out into the fresh air and then all of a sudden life has to change.
Sydney sadly became very anxious and depressed.
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Chapter 4: Who were Bailey Boswell and Aubrey Trail, and what was their connection to Sydney?
And I don't want to imply that all of that was down to her scoliosis and this sudden change of lifestyle because there could well have been other factors contributing to it. In fact, there probably were. She was a teenage girl at the end of the day. There's a lot going on for a teenage girl. But Sydney went through a real tough time as a teenager.
But luckily, she had all the love and support from her friends and family to help her through. Her siblings were like her best friends, especially her younger sister Mackenzie. They had so much in common, even the same friend group. They would hang out together all the time, they would drive around, they would take selfies together and post them online.
Sydney was such a sweet, caring, loving girl. She was known for her helpful, generous, selfless nature. In fact, her brother even said that Sydney was the poster person for caring more about others than she did herself. So naturally, in her time of need when she began to struggle, everyone locked in to help her get through it.
But sadly, that depression and mental struggle never really went away. Even after she graduated high school in 2011, she got her first full-time job at a home improvement store, she was entering the next chapter of her life, but it was all still very difficult for her. I'm sure it didn't help when her two siblings moved out of the family home and then it was just Sydney and her parents.
Of course, she wasn't alone, but the house will have been much quieter when her two built-in best friends were now miles away. But Sydney Loof was a resilient girl. She knew that she wanted a lot out of life and this wasn't how she wanted to be living it. And so in her early 20s, she reached out for help and was put on medication.
Shortly after, she moved out of her family home and to another town closer to her siblings She kept her job but she just transferred to a different location and she began building an adult life for herself now. She made a close circle of friends including a best friend named Brooklyn and Sydney even got a kitten.
And if there's one thing that I can personally recommend to help a struggling girl in her 20s, it's getting a cat. Or two, in my case. Sydney called her new baby kitten Mimsy and this cat became her whole entire life. There's something so special about having a pet at home when you're struggling.
It gives you a reason to get up every day and to live a functional life because it doesn't just affect you anymore, someone else is dependent on you providing for them. Not to mention just having a little guy in the house is so nice. I got my cats when I lived alone and it's just so wonderful having another living being in the house alongside you.
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Chapter 5: What evidence did police find linking Bailey and Aubrey to Sydney's disappearance?
You really do feel less alone. And Sydney was taking all of these super important steps to help herself out of this struggle. She was such a strong woman with a drive to live a very full life despite the hand that she'd been dealt. And going back to what I was saying a minute ago about her being so kind and so selfless, Sydney even at one point let one of her co-workers come and stay with her
while he too was going through a really hard time. He needed a place to crash. He needed friendship and advice and companionship. And Sydney wanted to provide that for him. She wanted to help people out of dark places because she knew what it felt like to struggle. And although Sydney enjoyed her job and she liked the people she worked with at the home improvement store,
She had big dreams of becoming a vet one day. Being able to work alongside animals from nine to five, helping them, cuddling them, curing them. It sounded like the most perfect, rewarding job that she could ever imagine. But for now though, Sydney's mind was elsewhere. She was looking for love. I haven't mentioned it before now but Sydney was an LGBT woman.
I don't know exactly how she identified but later in life we know for sure that she was looking for a woman. The reason I haven't mentioned it before now is because I couldn't really find any information at all in terms of like when she had this realisation or if it was something that was always known to her. I couldn't find anything along the lines of her coming out so
Naturally, I guess this is the first place that it comes up in our story. But Sydney lived in the middle of nowhere in Nebraska. There wasn't a huge pool of gay women for her to choose from. They didn't appear in her life organically very often. And so Sydney did what most people do these days. She made herself a profile on a dating app. Tinder, specifically.
But what Sydney didn't know was that there was one woman lurking in that app that wasn't searching for love. She was searching for a victim. So it was November 2017. 24-year-old Sydney Loof was swiping through Tinder, scoping out the potentials.
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Chapter 6: What were the details surrounding the discovery of Sydney's remains?
When she came across a woman she immediately liked. Her name was Audrey. She was 25 years old, brunette. Sydney thought she was super cute and so she swiped right. And it turns out, Audrey liked her too. And a match was made. The two of them began messaging and Sydney was trying to be hopeful about this connection, but she had been burned on dating apps before.
Not so long before this, she'd been chatting to another girl, even gone out on a date with her I think, but it turned out later down the line that she actually had a boyfriend. So pretty early on, Sydney knew that she didn't want to waste anyone's time. She wasn't prepared to be someone's secret experiment on the side. She wanted love with someone who was capable of loving her back.
And so she messaged Audrey in those first couple of days saying, look, If we meet up and if we go on a date, can it be just us two? And Audrey immediately put her at ease saying, yes, of course, lol. Perfect. It seemed that Audrey wanted exactly what Sydney wanted. They'd already been messaging for a couple of days, getting to know each other.
And so naturally, the next step was to go out on a date. They agreed to meet up on Tuesday, November 14th. The original plan was that they were gonna go and get dinner, they were gonna go to the casino, probably get some drinks, I'm sure. But once Audrey came to pick Sydney up, the two of them just got lost in conversation and they ended up hanging out in Audrey's car all night.
Despite its casualness, the date went well and it ended with Audrey dropping Sydney off at home. She was in work the next day where Sydney told all of her co-workers about that fabulous date that she'd been on the night prior, how well it had gone and how she was already making plans to see Audrey again. They were gonna meet up that same night. First date on Tuesday, second date on Wednesday.
Which I'm sure a lot of people would think is like way too fast but realistically if you're blessed with lesbian friends in your life you'll know that this kind of speed is standard practice. I'm not sure what it is, whether there's much of a reason behind it, but fact of the matter is lesbians move fast. Girls move fast.
So for people in the heterosexual dating climate, a second date on day two might seem like a red flag. And, you know, in hindsight, in this instance, it definitely was.
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Chapter 7: What was the outcome of the trial for Bailey Boswell and Aubrey Trail?
But Sydney wasn't necessarily doing anything that other queer women don't by doing this. While she was at work that day, on her shift, one of her managers actually asked her if she'd like to extend and do some overtime. But there was no chance. Sydney was making that second date. She had had such a great time with Audrey the night before that it was all she could really think about.
She was so excited to see her again. They'd even been messaging on Tinder in the meantime, like, just checking in and seeing how each other's days were going. And when Sydney finished up her shift that night around 6pm, she hopped in her car and headed home to freshen up and get ready for the date. I'm not sure what specific plans they had for that night, if there were any.
Maybe they just planned to hang out in Audrey's car again since The conversation seemed to carry so well last time. But Sydney got ready in her apartment, she put on a white shirt, some jeans, and she quickly snapped a selfie before she left, captioning it, ready for my date, and she put that on her Snapchat story. At 6.45pm, a message popped up from Audrey.
She was downstairs, ready to pick her up. And with that, Sydney headed out. Only, the person waiting downstairs wasn't really Audrey. And Sydney wasn't heading out on a date. She was walking into a trap. The following day was Thursday, November 16th, 2017. Sydney was supposed to be working the morning shift, but she never turned up. Already, this was out of character. Sydney was very reliable.
She was a punctual worker who would communicate clearly with her manager before taking any time off. So there was an immediate concern that something wasn't okay. So her manager called her up. but it went straight to voicemail. So they left it a couple of hours thinking that Sydney would either just show up late with a reason or eventually call in and explain where she'd been.
But as minutes turned into hours and hours became her whole shift, It was clear that something was wrong. Her boss got in contact with her parents now, out of concern.
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Chapter 8: How did Sydney's case raise awareness about LGBTQ+ safety in dating?
She wanted to know if they'd heard from Sydney and if she was okay. But it was this phone call that made her parents realise that they also hadn't heard from their daughter all day. And come to think of it, when her mum had sent her usual goodnight text the night before, she hadn't heard back. which was equally out of character for Sydney.
So now everyone's trying to call her and text her, her co-workers, her mum, her dad, and it's still going straight to voicemail. Her phone had either run out of battery or been intentionally switched off for hours.
Her family got in contact with all of her friends and none of them had heard a peep out of her since yesterday, since she'd posted that selfie on her Snapchat story talking about going on a date. Everyone was panicked beyond belief now. There was nothing normal or explainable about this, and so Sydney's parents rushed down to their local police station to file a missing persons report.
Meanwhile, a couple of officers were dispatched to where Sydney lived to go and perform a welfare check on her home. When they arrived, her car was still parked in the driveway, all of the lights were on inside, and her front door was locked. The police managed to gain entry to the property through an open window, and inside they found Sydney's cat, Mimsy, all alone.
Its food and water bowls were now completely empty. She hadn't been home to feed her cat. They also found Sydney's purse, along with her glasses,
Which was actually quite interesting because Sydney switched between wearing glasses and contact lenses, depending on the occasion, so her opting for contacts that day indicated that wherever she'd gone, she probably hadn't intended to stay there overnight because she would have had to take the lenses out before bed.
Now, officers had been told at this stage that the last thing that Sydney posted online was her Snapchat story, talking about how she was going on a date that night. Of course, it was immediately concerning to them that she'd gone out to meet someone that was presumably a stranger, or at least close to a stranger, and she'd never come home again.
That same day, a Facebook page was created with the goal of getting Sydney's photo out there. Surely someone had to know something. Someone had to have seen her in this time. This Facebook group became big, eventually amassing almost 30,000 members who could see and post any leads that they might have, any tips, any potential sightings.
Sydney's family and friends also printed missing persons posters that they tacked up all over town and handed out to people as they were walking past. And these flyers were really descriptive as well. They had pictures of her very distinctive tattoos including a yin and yang that had this like pattern detail in it and cursive text on her arm that read, everything will be wonderful someday.
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