23-Year-Old Woman Moves in With Boss After Matching on Dating App

Genevieve Scott

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Instagram via @lianamdwfeatures

"It's no question that when you share your love life on the internet, people are going to have some opinions," Alyssa explained. Sure enough, after sharing hers, she may have let on a little more than she'd intended.

An Unexpected Love Story

"Were the circumstances that we met under the best? No. Did we make the best out of it? Yes," Alyssa confessed of matching with her boss on a dating app. Since then, her life has never been the same.

Rick, Alyssa, Age gap
YouTube via truly

But the truth is that she wouldn't want it any other way. Despite her and Rick's 36-year age gap, the couple has defied just about every odd. As for how they first came to be? From their very first meet-up to coming clean to their co-workers, here's their captivating story.

Enter Alyssa

Nearly everything about Alyssa Cleland's life was unique. In fact, long before her love life was called into question, Alyssa was busy battling other obstacles. "I was born in Ukraine. From what we know, my mother was super young," she revealed of the moment she entered this world.

Alyssa Cleland, Dating, Boss
YouTube via truly

Unfortunately, her birth mother was simply not ready for parenthood, and the infant was left abandoned. But believe it or not, Alyssa didn't spend her first year in an orphanage or children's home. Instead? Her reality called for daily doctor visits and hospital rooms.

She Was Born Different

"I was born with a rare congenital disease," Alyssa explained. She was diagnosed with Paraxial Tibial Hemimelia, a condition affecting only one in a million people. As a result, she spent the first year of her life in a hospital, fighting for her life. But to her doctors' amazement, she put up one heck of a fight.

Alyssa Cleland, Age gap
Instagram via @alcequine

Despite never developing her middle fingers or the tibia on her right leg - deeming her unable to walk - Alyssa was eventually discharged from the hospital. Upon her release, she was welcomed into a nearby orphanage. But she wouldn't be staying long. Life as she knew it was about to change, forever.

She Was Adopted By an American Family

After three seemingly endless years in the orphanage, the toddler's reality brought her halfway across the globe. "I was adopted from Ukraine at the age of 4," Alyssa revealed of Joe and Robyn Cleland, her adoptive parents who welcomed her into their home with open arms.

Alyssa, Rick, Dating, Boss
YouTube via truly

But the young girl's latest chapter didn't just call for a new household. After undergoing surgery to install a prosthetic on her right leg, Alyssa was officially able to walk. For the first time in what seemed like forever, she was suddenly hopeful about the future.

She Loved Horseback Riding

Ever since taking her first steps, Alyssa's path has led to endless adventures. From baseball to volleyball to triathlons, there wasn't a sport the young girl didn't play growing up. But there was one hobby in particular that soon stood out from the rest.

Alyssa Cleland, Boss, Dating
Instagram via @alcequine

Horseback riding: A thrill Alyssa simply couldn't get enough of. She wanted to spend the rest of her life in the stables - and she soon would. Only as she packed up her bags and set out to do exactly that, her life was about to change in more ways than she could've ever imagined.

She Moved To Pursue Her Equestrian Dreams

As the story goes, after graduating from high school in 2015, Alyssa welcomed a new chapter with open arms. In 2018, she said goodbye to Southern California and headed out East to make her dreams a reality: She was going to compete in the 2024 Paralympic Games.

Alyssa Cleland, Age gap
YouTube via truly

Only as she stepped off that plane in Dallas, Texas, a new wave of thoughts suddenly crossed her mind: How would she pay the bills for her new place? And perhaps more importantly, how would she fund her love of horseback riding? She needed a job, savings to help make her dreams a reality.

Meet Rick

Which brings us to a special somebody: Meet Rick Madson, the other half of our story. Back in 2018, the 56-year-old divorcé was living an ordinary life when everything changed. He was the CFO of CBG Surveying Texas, a land surveying business with about 200 employees.

Rick Madson, Alyssa, Couple
LinkedIn via Rick Madson

But as his newest employee walked through the office doors, nothing would ever be the same. Any guess who we're referring to? Of course, Alyssa Cleland, the ambitious go-getter who was eager to get started in this new career. And it wasn't long before he took notice.

Alyssa Caught His Eye

Rick and Alyssa were practically destined to be together. Or at least as far as Rick was concerned. From the minute the California native walked into his office, there was something about her that caught his eye; Something he simply couldn't put his finger on.

Rick, Alyssa, Boss, Dating
Facebook via Rick Madson

"Right out of the gate when the company... hired her, I kind of noticed her," he confessed. How did he put it? "She sort of stood apart from everybody else, because she had this energy." Little did he know, that same attraction would soon lead him down a slippery slope.

He Matched With Her on a Dating App

Sure, Rick was intrigued by the charismatic woman who just joined his team. But the truth was that when he wasn't working 9-5, his mind was completely elsewhere. The divorced step-father was determined to find love again and spent his nights experimenting with dating apps.

Alyssa, Rick, Match, Boss
YouTube via truly

But one fateful night, as he scrolled through his notifications, he couldn't believe his eyes: He matched with someone! Only as he raced to check his inbox, Rick was left… confused: He recognized the girl smiling back at him - but from where? Who was she? And why did she look so familiar?

Alyssa Instantly Recognized Him

As for who our mystery woman was? Of course, 20-year-old Alyssa. But while she may have also swiped right, there was no confusion on her end. She suddenly recognized her latest match - the charming middle-aged man - staring back at her on her screen. And she decided to take action.

Alyssa Cleland, Age gap
Instagram via @alcequine

"What are you doing? We can't date," Alyssa confronted Rick on the dating app. She couldn't help but call him out on his seemingly questionable behavior. But aside from the fact that he was her new boss, there was another factor that was cause for concern.

She'd Dated Older Men Before

Sure, he was her boss, with several years at CBG Surveying Texas over her. But their differences went far beyond their time at the same company: He was 56, and she was 20. What would their co-workers think about their 36-year age gap? Or better yet, how would onlookers feel if they headed down a romantic path?

Alyssa, Boss, Age gap
Instagram via @alcequine

But the truth was that none of that mattered. At least where Alyssa was concerned. Before stumbling across Rick online, she'd actually dated a 54-year-old man; A relationship that spanned almost half a year. But how would her latest suitor feel about their age gap?

Rick Hadn't Realized Who Alyssa Was

Sure enough, after reading the words now flooding in his inbox, Rick couldn't help but feel flustered. As Alyssa reminded him, he had just approached one of his employees on a dating app. He was mortified, and then some. And Rick rushed to set things straight.

Rick, Alyssa, Dating, Boss
YouTube via truly

"The thing is, for whatever reason, I didn't connect that picture and her profile with the girl from work," Rick explained as he apologized to Alyssa for the misunderstanding. But "sorry" wasn't the only thing the embarrassed CFO had to say for himself.

He Asked Her Out To Clear the Air

Rick wasn't just apologetic. He was worried, and then some. His status at the company was officially at stake; All because of an honest misunderstanding. "I had a lot to lose if I'm the guy in the corner office, and here's somebody that just started," he explained of matching with Alyssa.

Rick, Alyssa, Boss, Date
YouTube via truly

"You can't do that in a company." Rick needed to clear things up. And that's exactly what he set out to do as he invited Alyssa out to lunch - to "clear the air," as he assured. "I wanted to diffuse [the situation]." But how would Alyssa take his offer?

Alyssa Agreed To Meet

Alyssa had a decision to make, one that left her mind running in circles. Here was her boss, trying to smooth things over and make things right. But would everybody else see it that way? They probably wouldn't, she thought. But how could say possibly say, "No?"

Alyssa, Dating, Age gap
Instagram via @alcequine

Finally, after weighing out all of the options, Alyssa made a decision. Granted, not everybody would agree with it, but she was sure it was the right move. Only as she headed out the door to meet her boss for lunch, she couldn't fight the butterflies now hijacking her stomach.

They Instantly Hit It Off

What would they even talk about? What if Rick was actually interested in dating her? And perhaps more importantly... what if she wanted him to be? Safe to say, all of those concerns suddenly vanished the minute she came face to face with Rick Madson.

Alyssa, Rick, Age gap
Instagram via @lianamdwfeatures

The sparks were simply undeniable. And in the blink of an eye, 4 hours had suddenly passed them by. Alyssa was left completely smitten by the person sitting before her. And so was he. "I think he was still toying with it, I was half expecting him to kiss me... but he didn't," she confessed.

Rick Was Charmed by Her

Rick's attempt to clear up any confusion had actually left him more confused than ever before. Alyssa was everything he was looking for in a partner, and then some. "She spoke with passion and purpose about just day-to-day stuff, and I thought it was very cool," he revealed.

Alyssa, Rick, Age gap
Instagram via @alcequine

As they laughed together at that lunch table, Rick couldn't fight the emotions he was suddenly feeling. "She had a super cute smile, and we just connected," he explained. But while chemistry may have been in the air, there was also an elephant in the room; One he couldn't ignore.

He Quit His Job

Rick had to sit down and face the facts: He was the CFO of a thriving company, a career he'd spent endless years building up. But heading down a romantic path with Alyssa would destroy all of that. Wouldn't it? He had to decide what mattered more - before it was too late.

Rick, Boss, Dating, Alyssa
YouTube via truly

Would he stay with a company he poured all of his time and energy into? Or would he give all of that up for a woman he'd just met? After 6 long weeks, he finally reached a decision: "We won't go into the details, but I was no longer with the company," he revealed as he stepped down from his position as CFO.

They Became Official

"Once I left the company, I was like, 'Okay, that's it,'" Rick explained of the realization that followed. His career may have been up in the air, but there was one thing he was suddenly sure of: "We're going out," he assured Alyssa as she welcomed his resignation with open arms.

Alyssa, Rick, Dating, Boss
Instagram via @alcequine

As for what came next? It all happened so fast. "Once we started seeing each other, it was like we saw each other almost every day," Rick revealed. "It was really like, boom, boom, boom; we accelerated pretty quickly." But their love story was just getting started.

She Moved in With Him

Mere months later, Rick and Alyssa went from co-workers to partners to... living together. "She had some stuff going on with her roommates," Rick revealed of the moment he gifted his girlfriend a key to his place. "I was like, 'Just move in,'" he explained.

Alyssa Cleland, Boss, Dating
Instagram via @alcequine

But how would their latest chapter pan out? After all, there was still so much they had yet to learn about one another. What if they didn't like what awaited them under their shared roof? Safe to say, the events that followed surprised even Rick and Alyssa.

They Were on the Same Page

"Things were just easy with him, and I felt very comfortable around him," Alyssa gushed. They were on the same page - about seemingly everything. "Since Rick was so much older and had a ton of insight, the communication between us was a little easier," she explained.

Alyssa, Rick, Boss, Dating
YouTube via truly

How did Rick see it? "She was mature beyond her years, always positive and somebody that inspired me by the way she carried herself," he boasted about his new girlfriend. They were like night and day. And yet, somehow... it worked. It was truly a sight to be seen.

Alyssa Wasn't Fazed by the 36-Year Age Gap

Sure, their bond was constantly evolving - strengthening. But there was another factor in their relationship they simply couldn't ignore: Their 36-year age gap. Rick and Alyssa had decades wedged between them, something they'd have to face eventually.

Alyssa Cleland, Age gap
Facebook via Alyssa Cleland

"I think a lot about what the rest of my life's gonna look like," Rick confessed. "But after [10-15 years]? You know, all bets are off." But the uncertainty doesn't scare Alyssa. "I wanna see where it goes," she admitted. "If it means I'm changing his diapers? I'm changing his diapers… I'm in it for the long haul."

Her Plans for Starting Their Own Family

But while Alyssa might be in it for the long haul, what exactly would that look like? Might wedding bells be in her and Rick's near future? What about a family of their own? With Rick almost pushing 60-years-old, would they even be able to have children together?

Alyssa, Rick, Age gap
Instagram via @alcequine

For starters, "I'm just waiting for a ring at this point," a hopeful Alyssa confessed. But believe it or not, she doesn't share that same optimism when it comes to starting a family. "We talked about our future, and we both don't want kids," she explained.

She Was Accused of Having Ulterior Motives

With their values seemingly matched up, Alyssa and her boyfriend are excited about the future. Unfortunately, not everybody feels that same way. The truth? "It's no question that when you share your love life on the internet, people are going to have some opinions," as Alyssa confessed.

Alyssa, Rick, Boss, Dating
Instagram via @alcequine

From being labeled a "gold digger" to a "woman with daddy issues," the negative comments hurled Alyssa's way have been endless. "Date someone 36 years older than you, and people will really tell you what they think," she quipped of the online skeptics.

Their Friends & Family Had Questions

Unfortunately, the skeptical words she's been met with go far beyond the keyboard: She and Rick's family and friends have questions, lots of them. And they haven't been shy making them known. "I've met a few of Rick's friends, and a couple of them thought I was his daughter," Alyssa revealed. "That was interesting."

Alyssa, Age gap, Boss
Facebook via Joe Cleland

But that's not all. Even exciting milestones, like house hunting, have been soiled by judging eyes. "When we were looking at places to live, some of the real estate people would point out the two separate bedrooms, which just made me call Rick 'babe' the whole time we toured places," Alyssa joked.

Where Are They Now?

There's no doubt about it: Rick and Alyssa's striking journey has captured the attention of both skeptics and supporters alike. But where does that leave them today? Has the unconventional couple continued to defy all odds, proving judging spectators wrong?

Couple, Age gap, Boss
YouTube via truly

Or perhaps were those skeptics onto something when they questioned the pairing of a 20-year-old and her 56-year-old boss? Unfortunately, Rick and Alyssa's story doesn't quite have a happy ending. Fast forward to today, and the two are no longer together. What happened?

They Broke up After 2.5 Years

"I've been dreading writing this post… it's one I had hoped I would never have to write," Alyssa revealed. On November 2, 2020, the now 23-year-old sent the online world buzzing as she opened the lid on her and Rick's relationship. Safe to say, it left spectators with lots of questions.

Alyssa, Rick, Dating, Boss
Instagram via @alcequine

But it appears there's no bad blood between her and her newfound ex. "I just want to say, it was a mutual breakup - we're still friends & will always be a part of each other's lives," Alyssa assured. "The last 2.5 years have been the BEST & I can not thank Rick enough for everything." But what went wrong exactly?

Their Age Gap Got in the Way

To put it simply, life happened. "Without going into too much of our lives, we ended things because our wants changed," Alyssa revealed: She wanted to get married, Rick did not. She enjoyed going out and "having fun," he opted to stay home. They were on two different pages.

Rick, Alyssa, Age gap
YouTube via truly

"I guess you can say the age gap did get to us as ours was pretty large," she confessed. "But despite the gap, we got along blissfully." Nonetheless, facts are facts. And "as we've grown as people over the last few years, we've changed," Alyssa continued to explain.

What Next

Well, what now? Where does Alyssa go from here? After calling it quits with her now 58-year-old boyfriend, the 23-year-old's reality looks very different. "I've decided to move out of our apartment and into one of my own," she proudly revealed on Instagram.

Alyssa, Age gap, Boss
Instagram via @alcequine

But while her future might be unclear, she's actually excited for what lies ahead. "I think this will be a great thing for me," Alyssa gushed. "For right now, nothing else has changed, but I'll really be taking this time to focus on me... everything I want to do."

Defying All Odds

Safe to say, her time of self-reflection has been nothing but rewarding. Alyssa Cleland's list of accomplishments only seems to be growing by the day. From surfing with pro-surfer Bethany Hamilton in Kauai to making the horseback riding regional Championships in 2018, Alyssa is officially a woman on the move.

Alyssa, Rick, Age gap
Facebook via Alyssa Cleland

As for what comes next? "I can see the light at the end of the tunnel," Alyssa gushed of her new chapter. While we can't tell you what exactly the future has in store, we've got a feeling this is only the beginning. And we can't wait to see where Alyssa's next steps take her.

The Takeaway

Nothing about Alyssa's journey to finding love is ordinary. In the span of a few years, we watched her defy all odds as she followed her heart to Rick Madson. And even though the two might not be together anymore, perhaps we can all learn a thing or two from them.

Alyssa, Rick, Age gap
YouTube via truly

"No one knows how long we have on this earth," as Alyssa put it. "And so I think just spend it with the people you love despite [potential risks]. It's all we can really do... to decide for ourselves what we want our lives to look like." Because after all, who knows what tomorrow might bring.