There was nothing amiss at Jennifer “Jenn” Kesse’s condo in Orlando, Florida on the day she vanished 14 years ago. It was January 24, 2006. Nothing out of the ordinary for someone getting ready for work. There were still puddles of water in the shower. A damp hand towel draped over the side of the sink. Hair and makeup items strewn across the counter. On her unmade bed was a selection of work clothes.
“We feel like she got ready to go to work,” Jenn’s mother, Joyce Kesse, told Dateline in a 2006 interview, just 100 days after her daughter was reported missing. “She left. She locked her door. And that is where the mystery starts.”
This week marks 14 years since Jenn disappeared from their lives.
The 24-year-old intelligent, adventurous spirit, who always wore a smile, had a bright future ahead of her. She was a college graduate of the University of Central Florida. She worked as a financial analyst for Central Florida Investments Timeshare Company and had been promoted twice within a year.
Two months prior to her disappearance, Jenn had purchased her first condo at Mosaic at Millenia Condominium in Orlando. And she was in a committed relationship with her boyfriend, Rob Allen, who lived in Ft. Lauderdale.
“We had an incredible relationship. It was long-distance, but we made it work,” Rob told Dateline this week. “When you find that instant connection with someone, you find a way to make it work.”
Jenn and Rob met in January 2005 when Rob was in Orlando with his roommate for a trade show.
“We were there for my roommate’s trade show, and it was also just a fun single boys weekend, you know? And one night, we were out at a bar and met Jenn and her friends,” Rob said. “We kept in touch and it just blossomed from there.”
Rob told Dateline he talked to Jenn multiple times a day, sometimes for hours at a time.
“You know that feeling, when you don’t want to get off the phone because you enjoy talking to the person so much?” Rob said. “That’s how it was with Jenn. Three and four hours would pass, and we’d still be talking.”
From January 2005 until January 2006, Rob and Jenn traveled back and forth between Orlando and Ft. Lauderdale to see each other, and also traveled together internationally as much as they could.
“Jenn was spontaneous and adventurous,” Rob said. “She was up for anything and willing to travel anywhere and try new things.”
Their last trip together took them to the island of St. Croix in the Caribbean. When they returned to Rob’s place in Ft. Lauderdale on Sunday, January 22, 2006, Rob said neither of them were looking forward to getting back to reality.
“We had just returned from holiday -- which was so amazing -- but now we were both dreading going back to work,” Rob said. “Jenn stayed with me that night and decided to drive straight to work early the next morning.”
Jenn left Rob’s place in Ft. Lauderdale in the early hours of Monday, January 23, 2006. She drove the two and a half hours directly to her job in Ocoee, Florida, where she worked a full day.
Over the course of the day, Jenn was in touch with her parents, her brother, Logan, and Rob.
“We were a close-knit family. Always in contact with each other,” Jenn’s father, Drew Kesse, told Dateline. “There’s really nothing Jenn wouldn’t tell us.”
Drew paused, softly laughed, remembering the one thing that he actually hadn’t known about his daughter.
“She didn’t tell me about her shamrock tattoo,” Drew said. That was something she had only told her mother.”
Jenn’s mother, Joyce, told Dateline she felt fortunate that their family was able to all speak to Jenn that day.
“I’m forever grateful for that last conversation I had with Jenn,” Joyce said. “I hold onto that memory, her voice, and her laugh. And I have the hope that I’ll hear it again.”
Jenn also spoke to her 21-year-old brother, Logan Kesse, that day. Logan and several friends had stayed in Jenn’s condo while she was on vacation and one of his friends left his cell phone behind. They talked about shipping the phone back to his friend.
Logan and Jenn were not only brother and sister, they were best friends. When they reached their 20s, their bond grew and their social circles merged. Logan, an avid soccer player, began to hang out with Jenn’s guy friends, who also played soccer. He added that Jenn was always very supportive of his sport and came to every game. When she went off to school at UCF, Logan visited on weekends just in time for the college parties.
“She was always, you know, a ‘big sister’ and I know for a long time, I was the annoying younger brother, but as we got older, we grew closer, just naturally,” Logan told Dateline. “That’s why this is so ridiculously difficult to deal with. Difficult then, and still difficult now, 14 years later.”
“I talked to her on the phone for the last time that day,” Logan said. “And I never thought it would be the last time.”
Later that evening, the last person to speak on the phone with Jenn was her boyfriend. It was about 10 p.m. Monday when they spoke, Rob told Dateline.
“It had been a long day, coming back from the Caribbean, and we were both tired,” Rob said. “We had a bit of a disagreement. She wanted assurance that I loved her. And to make sure I was in it for the long haul. Just normal relationship things. But everything was fine.”
The next morning, Jenn was gone.
Rob told Dateline that Jenn always contacted him in some way, by calling him or texting him, before she left for work — but not that day.
“I overslept, which is pretty normal, Jenn always got up earlier than I did anyway, and so she would always call and wake me up or at least text me,” Rob said. “But when I woke up that day, there was nothing.”
Rob tried to call Jenn as he rushed to work, but got her voicemail, which he thought was odd. He had a meeting at 9 a.m., but when it was over, he tried to call Jenn again, this time to tell her about something that had happened in the meeting.
“Jenn was a great sounding board,” Rob said. “She was the first person I’d go to when I needed advice, or just when I wanted to tell her something interesting or funny.”
But that day, Rob’s calls and texts to Jenn went unanswered. And by lunchtime, he was worried.
“It was odd that she hadn’t called me back,” Rob said. “Something wasn’t right. But at first, I didn’t think anything bad, like really bad, had happened to her. My mind just didn’t go there. You never think something like this could ever happen to someone you love.”
It was early that Tuesday morning when Jenn didn’t show up for an important meeting at her job that her employer and co-workers became concerned because they knew it was very unlike her to miss work.
They tried to contact Jenn, and around 11 a.m. when she still could not be reached, her employer -- who knew Jenn’s father -- decided to call her parents.
“We knew right away that something was wrong,” Drew Kesse told Dateline. “It’s not like her to not show up for work. She’s the most responsible person I know. If she knew she would be five minutes late for work, she would call them… that’s just who she is.”
Both Drew and Jenn’s mother, Joyce, tried to call their daughter, but their calls and texts also went unanswered.
“I called and I called and for the first time since Jenn was a teenager, it went straight to voicemail,” Drew said. “In that second, I knew something was wrong.”
They called Jenn’s brother, Logan, who was at the gym, and the three of them drove two hours from their home in Bradenton, Florida, to Jenn’s condo in Orlando.
On the drive down, Drew called a building manager at her condominium to check for Jenn’s car. Her black Chevy Malibu was gone. They gave two managers permission to go inside her condo to check for anything unusual. The door had been locked and nothing was out of the ordinary for someone who had gotten ready for work that morning.
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“Immaculate apartment, except for the bathroom being a mess, of course, that was typical,” Joyce said. “Shower was wet. Blow dryer out. Clothes on her bed. Other than that, the apartment was completely normal.”
Jenn’s luggage from her trip was still in the front hall, untouched. There were no signs of struggle or forced entry.
Her purse, keys, cell phone, and iPod, which family members said she always kept with her, were missing.
Jenn’s parents said it appeared she had gotten ready for work that morning and left, just like any other morning.
Drew told Dateline that authorities from the Orange County Sheriff’s Department and the Orlando Police Department arrived on the scene, but said they did not seem overly concerned because Jenn was an adult.
“They told us, ‘Oh, she’s an adult, she had a fight with her boyfriend, she’ll be back,’ and they left,” Drew said. “But no, she would not do that. She wouldn’t just up and leave.”
Detectives checked for activity on her ATM card and pinged her cell phone. There was no response.
Given the scene of Jenn’s apartment, authorities began to think Jenn was abducted during her walk to her car or on her way to work.
Family members and friends began the search immediately. They made fliers and distributed them around the area, pleading for answers.
Jenn’s boyfriend, Rob, and Rob’s mother, drove up from Ft. Lauderdale as soon as he heard Jenn was missing.
“I remember talking to my dad on the drive up and he told me, ‘You know, you’re the boyfriend, they’re going to look at you,’” Rob told Dateline. “But I knew I had nothing to hide. I can’t even imagine how horrific of a person you have to be to abduct someone or harm someone. I just knew I had to get to Jenn right away.”
Rob, along with Jenn’s parents and brother, were all ruled out as suspects right away, according to the family’s legal team and private investigator, Mike Torretta.
“I know that as the boyfriend, I’m prime suspect number one,” Rob said. “But no one treated me like that. The community was supportive and the Kesse family treated me like a son. They still do.”
As the investigation began, Rob camped out on the couch at Jenn’s condo for weeks. Jenn’s parents also stayed at the condo, for months, in an effort to make a statement that finding their daughter was the number one priority.
“Rob was so supportive then, and continues to be supportive. He was so brokenhearted,” Drew said. “He gave his life searching for her as much as we did. He’s part of our family and always will be.”
Jenn’s disappearance wasn’t the only heartbreak for Rob that year. Five months later, his father died.
“It was a double whammy, losing Jenn and then losing my father,” Rob told Dateline. “To lose the two most important people, other than my mother, in my life, was devastating.”
In the years since Jenn vanished, Rob has gotten married and had two children.
“I was just Jenn’s boyfriend. I could never imagine what her parents were going through,” Rob said. “But now that I have kids, I have a different understanding of what it would be like, and it’s heartbreaking.”
Authorities began to investigate the multiple construction workers and day laborers who worked in the area of Jenn’s apartment complex, which was only half-finished when she moved in two months prior to her disappearance. The Kesse family told Dateline that while they were at Jenn’s, workers were in the condo across the hall installing new carpet.
Mike confirmed to Dateline that many of the workers were allowed to stay in the empty condos in the complex which, according to family members, made Jenn uncomfortable.
“There were a few times, Jenn told me, that the workers would just stop and stare at her,” Joyce told Dateline. “A few friends told her that if the workers started to verbally harass her, to go to the manager, but thankfully it never escalated to that. Or not that we know of anyway.”
Rob told Dateline that Jenn had expressed to him that she felt uncomfortable at times and wasn’t thrilled living alone.
“She always said she felt safe with me, so I feel emasculated that I wasn’t there to protect her, to save her.”
A few days later, on January 26, 2006, came the first big break in the case. After seeing Jenn’s story on the news, a resident of the Huntington on the Green condominiums, reported seeing a black Chevy Malibu that matched the description of the one Jenn owned. The condominiums are about a mile from where Jenn lived. Authorities arrived and confirmed the car was Jenn’s.
“But there was no evidence in that car, not any that was recorded in the police reports,” private investigator Torretta told Dateline. “There was no blood, no DNA, no hair samples, nothing.”
Jenn’s purse, cell phone and iPod were nowhere to be found.
The only evidence was surveillance footage obtained by Orlando Police that showed an unidentified person walking in the parking lot at the same time Jennifer’s car was left in the lot -- 12 p.m. on Tuesday, January 24, 2006.
Jenn’s father Drew told Dateline the footage proved to be frustrating because the camera was programmed to take pictures every three seconds and unfortunately, in each frame, the suspect’s face was obstructed by a gate post.
According to private investigator Torretta, the “person without a face” is a “person of interest” and the main focus of his investigation.
Despite photo enhancements by the FBI, who briefly took over the investigation in 2008, investigators were unable to determine if the individual is a man or a woman. The only thing police can determine for sure is that the suspect was between 5’3” and 5’5 inches tall.
“That person is the key,” Torretta said. “If we know who he or she is, we can find out where Jennifer is.”
Police searched the area with dogs, horses, and search parties. The Kesse family organized volunteers to pass out fliers and spoke on local and national TV. They generated thousands of leads and tips, but the ultimate tip has still not come through.
For 14 years, Jenn’s family has not given up their search for her.
Jenn’s brother Logan was scheduled to move to California to be with his girlfriend just a week after Jenn disappeared. But instead, he stayed.
“There was no question,” Logan told Dateline. “I had to stay and find my sister.”
Instead of moving, Logan traveled back and forth between Florida and California, and got his real estate license. Over the years, his parents encouraged him to travel and to enjoy his 20s.
“It submerged our lives for so long. It still has for my parents,” Logan said. “I wanted to just sit there and wait for her to come back. But she didn’t come back. It’s been 14 years and she’s not back. And it puts life in perspective. That’s when I decided to travel, start my career. I got married and had kids, I had to keep going.”
Logan moved away from the area with his wife and children, but told Dateline he will never stop looking for his sister.
“Until the day I die. I won’t stop looking for her,” Logan said. “Won’t stop looking for answers. And I won’t stop until someone is held accountable. For her disappearance and for the fact that it’s gone on this long without answers.”
Logan said he believes one of the workers from her apartment complex is to blame.
“I personally have never really wavered on what I think happened, but of course the mind can be pulled into so many different directions because we have nothing concrete,” Logan said. “We don’t know anything. But I have this gut feeling that one of those workers knows something.”
Jenn’s family told Dateline their frustration with how local authorities handled her case grew over the years and in 2018, they decided to take the investigation into their own hands.
Drew and Joyce took legal action against the Orlando Police Department in order to gain access to Jenn’s case files.
“On every level, Jenn’s case has been a challenge,” Drew told Dateline. “As of right now, there is no law enforcement working on my daughter’s case. It’s all me -- my family. And that’s not how it should be.”
The Orlando Police Department did not immediately respond to a request for comment from Dateline.
In 2019, the family won their legal battle and received more than 14,000 pages of electronic files and hours of video from the Orlando Police Department. A legal team and a handful of investigators, including Mike Torretta, have been helping them sift through the files for months.
“We needed the files for answers,” Logan said. “But what we got was a mess. It looked like they knocked a filing cabinet over, shuffled the papers and handed them to us.”
The family said there was a seven-year gap in the case files where nothing was recorded.
“Nothing was done, no investigation,” Jenn’s father Drew said. “They told us it was an active case. But nothing -- absolutely nothing -- was being done.”
On November 8, 2019, for the first time in years, there was a second possible break in the case. Investigator Torretta discovered, deep in the files, a tip from a woman who, in 2006, said she witnessed “something strange” at Lake Fischer in Orange County on the day of Jenn’s disappearance. Torretta spoke to her and said she told him she saw a man drive a pickup truck to the lake that Tuesday in 2006, take out what appeared to be a six to eight-foot piece of rolled-up carpet and dump it in the lake, watching it sink.
Drew’s investigative team began searching that area with their own private cadaver dogs and were alerted to something.
“We had a hit,” Drew said. “Something was there.”
Deputies from the Orange County Sheriff’s Department were called to the scene, but after deploying a dive team and cadaver dogs over a three-day search, the sheriff's office confirmed to Dateline they came up empty handed.
Investigator Torretta told Dateline he wants another chance to search the lake because a clue from Jenn’s apartment complex could be submerged beneath the surface -- the old carpet being torn from the condo across the hall.
“We need to continue the search to at least find the remnant piece of carpet,” Investigator Torretta said. “If we can just find that, it might be the key we need to move forward and get to the bottom of where Jenn is and what happened to her.”
The Kesse family told Dateline they won’t ever stop searching for their daughter or for answers.
“This has taken everything out of us, emotionally and financially,” Drew Kesse said.
Joyce said she’ll never give up hope that her daughter is out there somewhere, alive, needing to be rescued.
“How do you decide, as a parent, when the right time is to give up the search for your child?” Joyce said. “You don’t.”
“It’s like Groundhog Day every day, yet, life moves on for everyone else,” Joyce said. “Sometimes it doesn’t feel like 14 years has passed. When I reflect back to that time, I feel numb.”
One of Jenn’s friends found out she was pregnant just after Jenn vanished. That baby is now 14 years old. Joyce now measures the years her daughter has been missing to the milestones of that teenager.
“To me, 14 years ago with my Jenn seems like yesterday,” Joyce said. “But when I see that baby -- now a teenager -- it’s a powerful and heart-wrenching reminder of how much time has passed. And how little of the window we have to find Jenn.”
Joyce told Dateline that the hardest part is being in limbo.
“If she’s not alive, we just want some kind of proof that she’s not with us anymore. The tiniest bone. Something. The hardest part is being in limbo. That’s hell. The nightmare – to not know. Drew and I are in our 60s. We just want to know where she is, what happened to her, before it’s too late for us.”