Woman Set Up on Blind Date by Boss, Horrified After Learning His True Identity

Olivia was struggling to find love in New York City. But when her boss offered to set her up on a blind date, she had no idea what awaited her. From hopeless romantic to heartbroken, this is her unexpected journey.

Meet Olivia

Meet Olivia Fenton, an “actor, singer and tall lady from NYC,” as her Instagram bio reads. As a former student of The Hartt School and actor of the Monomoy Theatre, Olivia was always the ultimate performer.

So, when Olivia found herself in this incredibly surprising situation with her boss, the 25-year-old did what she does best: used her theatrical abilities to entertain her TikTok followers with a hilarious confession. Understandably, people were instantly captivated. Here's why…

A Quest For Love

Searching for love in New York City has become a well-discussed topic. They’ve even made movies about it. With a population of almost 8.5 million, there seemingly should have been a number of eligible bachelors in the city for Olivia to date. But fate had other plans.

Sure enough, finding a suitor was no easy task for the hopeful romantic. And after no luck with dating apps and single networking events, Olivia was willing to give anything a try. Little did she know, that same open-mindedness would soon take her on a bumpy ride.

The Proposal

As the story goes, Olivia’s boss eventually heard about her quest for love. She had an exciting proposal for her employee! As she suggested, Olivia would be set up with her best guy friend - someone she believed would be an excellent match for the bachelorette. She was insistent that Olivia give him a shot.

After several bad experiences in the past with blind dates, Olivia was hesitant at first. However, after much convincing by her boss and the presentation of some very beautiful photographs of the bachelor, she agreed to give it a shot. It seemed like the perfect plan. For now, at least.

Arranging the First Date

Her boss passed on Olivia's number to her guy friend, and the pair began to text. After some initial chat, they agreed to go on a date and arranged the details. Olivia felt all the usual pre-date nerves and excitement but thought nothing of it. She headed to the bar...

However, after Olivia found herself waiting at the table alone, she realized he was a no-show. The ‘dream date’ she was promised by her boss had stood her up. But later that night, she received a sudden text from her mystery man, requesting a second chance at a date.

A Second Chance

Being the forgiving queen she was and knowing opportunities to date good guys don’t come around too often, Olivia agreed to give the man a second chance. She understood that issues do come up, and perhaps it was an honest mistake that he did not make it to the date.

They arranged the details of the date, and Olivia was again looking forward. Believe it or not, after arriving and waiting for the mystery guy, she realized he had, once again, stood her up. This time though, he had sent her a text immediately to explain his side of things...

Holding Onto Hope

As he put it, he had gotten stuck in work meetings and would be incredibly grateful for a third chance. Sure enough, perhaps more generous than the rest of us, Olivia gave this ‘no show’ a third shot at redemption. Again, they arranged a time and place. Surely, he wouldn’t stand her up again - after all, she trusted her boss.

She understood that the situation was different than if they had just met on an app. A total stranger with no mutual contact would owe her nothing. The phrases ‘third time lucky’ and ‘third time's a charm’ came to her mind, and she was confident this time would be different!

Triple the Confusion

As she prepped her make-up and hair for a third date with a guy she still had never met, Olivia promised herself this really was his last chance. So, when she sat at the bar, anxiously waiting for the handsome guy she was promised to walk through the door, she could not believe the events that soon followed.

Her date had stood her up, again. But as soon as she lost all hope in her mystery match, he texted her. As he put it, he indeed showed up at the bar but did not see her - so he left. He explained that he had attempted to return to the bar to find her once he knew she was there, but his train got stuck underground.

Closing The Chapter

At long last, after three failed attempts at meeting, Olivia had given up. She’d had enough of this man and his excuses. She would not allow herself to be hurt and stood up by this man again. As far as she saw it, she was simply wasting her time for which he clearly had no respect.

She messaged her boss to say, “look, it’s not going to work between us.” She was nervous about letting her manager down, who was so passionate about the idea of the match - but she had to put herself first. Her boss, however, viewed things differently.

A Christmas Request

A few months had passed, and Olivia had decided to put this entire dating fail drama behind her. Surrounded by her friends and family at Christmas, she felt happy and at peace with the influence of the Christmas spirit around her. And then her phone beeped...

She was shocked to look down and see this man’s name appear on her phone with a message. He was requesting one last shot to take her out on a date and prove his worth to her. A bold request on his behalf - but she had to respect his perseverance. He seemed to really want to meet her.

Stuck In A Dilemma

This time, Olivia was confused more than ever and unsure what to do. On the one hand, she had her boss's approval. Perhaps, all these misunderstandings and disturbances were not his fault and just a case of terrible bad luck - a coincidence on his end.

On the other hand, could she handle being hurt again? The rejection was starting to take a toll on her. But she knew nothing in life comes easy, and if she wanted to find love, she had to put herself out there. Finally, after much thought, she “stripped the humbug cloak off” her body and said, yes...

The Final Straw

As Olivia recalled to her TikTok followers, she "planned a redemption dinner for him" after agreeing to meet again. She saw this as his final chance to prove that he was indeed worth her time. And he truly seemed sincere this time. So when he did not show up to this date, she was left in complete and utter shock.

What was really going on here? He was the one who had chased her down and convinced her to give him another chance. Was she missing something? Sure enough, later that night, he messaged her to answer exactly that. As he put it, he had not shown up this time because he “had got into a car accident.”

More Questions Emerge

There was only so much disappointment Olivia could take. The young girl was understandably heartbroken. Sure, she had never met the man, and she knew it might seem silly to some that she was upset over him. But she had pushed herself to put herself back out there - only to be let down time and time again.

The rejected woman had questions - lots of them. Why had her boss vouched for a man who continued to let her down? Little did Olivia know, there was a shocking explanation behind all of her heartache. And in only a matter of time, she would learn just that.

Connecting The Pieces

After spending a few days mending her heart and feeling sorry for herself, Olivia started to reflect more critically about the events of the past few months. She had heard her friends discuss their lousy dating stories - but this one seemed a little too coincidental.

What were the chances that this mysterious man had been held up on four occasions, each time for a different reason? Something seemed off. Sure enough, Olivia decided she needed to dig deep to find out what was really going on. And that's when it hit her...

Gathering The Evidence

Was this mysterious suitor even real? Olivia began to gather evidence to back up her theory. If this guy was never real, then that meant her boss made him up. But why would she even do that? As crazy as it seemed, the young girl had a gut feeling that she was onto something.

Of course, before she accused her boss of such an unbelievable betrayal, she knew she had to make sure she was 100% right. She needed evidence to prove that her boss was behind this from the beginning. If not, the entire thing would blow up in her face. She had to tread very lightly.

Fact Checking

Over the next few days, Olivia got to work as a detective and discovered some startling details. As she later recalled in her TikTok video, she somehow discovered that her manager had purchased a burner phone in recent months. Was she the one behind all of those loved-up text messages?

But that's not all she found. Olivia also uncovered that the photos of her potential suitor that her boss had presented her with were of a random guy found online. And the handwritten note this "guy" had previously sent, along with flowers? Well, it matched the handwriting of her manager! Everything suddenly clicked into place.

The Moment of Truth

The evidence was all there in black and white. As much as she didn’t want it to be true, it all added up clearly: it was, in fact, her boss behind this saga from the start. This “best friend” had never even existed. Her boss had made the entire thing up. But why?

Olivia was in shock. She had been hesitant, yet her boss had insisted. She crossed the employer-employee boundaries by meddling in her personal dating life, only to send her on a wild goose chase in this cruel prank. Olivia felt an incredible sense of betrayal.

Exploring All Possibilities

The shocking discovery brought a new wave of questions for Olivia. She couldn’t understand why her boss did this to her and betrayed her trust. Was her boss angry at her for something she had done at work? Was this all a revenge plot just to humiliate her?

Did her boss find enjoyment and entertainment in messing with her employees and their love lives? Had she done this before to other employees? Did she think Olivia would find the entire thing entertaining and laugh with her later? Olivia needed to know what was really going on here.

She Shared Her Story

Perhaps in an attempt to get answers and maybe some clarity, Olivia took her TikTok account to share her remarkable story with her followers. "Catfished by my own boss! Has this also happened to any of you NYC girlies out there? I must know," she wrote.

Olivia recounted her story in a lighthearted 1 minute and 23-second video, where she seemed to find the humorous side to the incident. “Anybody else? Just me?” she ended off with a puzzled look on her face, presumably hoping others would relate to her story and come forward with some words of advice.

A Viral Reaction

There was no way Olivia could have expected the response she received. Her followers went crazy for the story, sharing it with their friends. Within a matter of hours, the video had over two million views, 487,000 likes, and 12,000 comments. It was picked up by papers such as the Daily Mail, The Mirror, and The New York Post.

There was a mixed reaction to the story. Although no one could directly relate to the story with a similar experience as Olivia hoped, many were alarmed and unsettled by this ‘catfish’ situation. Others seemed to be more entertained by the story’s twisted ending.

Filling In the Gaps

One thing all the viewers agreed on was that they wanted more information on the story. In their opinion, Olivia’s version of the events was far too brief. They had questions they wanted to be answered, and there were gaps in the story that they wanted to be filled in!

“We need so much more info RIGHT NOW,” demanded one fan. “So does she love you or hate you. I’m so confused why anyone would do this,” questioned another. There was an overall sense of “why?” that seemed to overwhelm the responses. Users could not understand why this woman would go out of her way to do what she did to Olivia.

Her Visit to HR

Just two days later, Olivia obediently returned to TikTok to give her fans all the answers they had demanded from her. "I'm here with hard-hitting information about my catfish situation," she announced to her eager followers. In a thirty second video, Olivia recounted all the events that had taken place since she first broke the story.

Turns out, after seeing comments on her video such as “What in the HR violation is going on here????,” Olivia began to realize the severity of the situation. She decided to go to her Human Resources department to file an official complaint against her boss.

A Vital Update

Immediately after reporting the incident to HR, Olivia discovered that her boss had been fired. Of course, this could not erase the dramatic ordeal she had been through - but at least she would no longer have to face her boss every day and could begin to put the situation behind her.

“Yes, my manager was fired. I went to HR, and they handled it immediately,” she explained in her second clip. There was no mention of whether Olivia had any direct interactions or confrontation with her boss herself following the big reveal of her date’s identity.

A Disturbing History

In a surprise turn of events, Olivia discovered that she was not her boss's first target. In this update clip, Olivia revealed that her boss had a track record of setting her employees up on dates and 'catfishing' them after. How her new company was unaware of this was unclear. 

“I also found out she did this to a woman at her previous company,” she explained. We can only hope that due to Olivia’s bravery in speaking out against her boss, more woman in the future will be saved from this experience. As to the rest of us, who may not ever meet Olivia’s boss, it can certainly act as a cautionary tale.

“What Were Her Motives?”

As soon as the video was released and the news of this woman’s deceptive habits were announced, people began to speculate why this woman had done this to her innocent employees. The majority of followers suggested that this woman perhaps had a crush on Olivia and wasn’t sure the best way to approach the situation.

Olivia confirmed these theories in her video: “What were her motives, you ask? A lot of you guessed correctly. It is speculated she is deeply in the closet and is coming to terms with her sexuality. So, I think she might have had a crush on me and just took it wayyy too far!”

Mixed Responses

In response to Olivia’s revelation about her boss’s motivation, the people, of course, had more to say. While most were angry with this woman for what she did to Olivia, some decided to take a more sympathetic approach. These users felt bad for the closeted woman who could be related to on some level.

One comment summarized the general feeling of the group, “I feel bad she’s closeted, BUT this was sooo inappropriate and not the way to explore her feelings by playing around with yours, especially because she’s your boss!” Others insisted “that’s not an ‘in the closet’ thing, that’s a ‘needs to see a therapist ASAP’ thing.”

Going Hollywood

Fans were quick to point out that Olivia’s story was so bizarre it sounded like the plot of a Netflix or Lifetime series rather than real-life. “It’s giving lifetime movie [vibes],” commented one user. “If you’re pitching a Netflix miniseries, the answer is yes; I will watch it. Release all ten episodes!” joked another commenter.

Overall, it seems clear that this story greatly entertained the internet, so much so that many believe it would work well as a dramatic movie. Should Olivia expect to receive an offer from Netflix in the coming weeks? The paycheck may help make the whole incident a little more bittersweet.

Where Is She Now?

Clearly, her striking story has caught many people’s attention. But as the weeks have gone by since her first video, we are curious to see how Olivia is getting on and dealing with the aftermath of her sudden viral fame. Where is the viral blogger today?

Checking out her TikTok, Facebook, and Instagram feed, Olivia seems to be all smiles and in great spirits - seemingly having put this entire crazy incident behind her. We were happy to see she is still pursuing a career in music and acting, posting numerous videos of her singing and acting with her friends and family!

A Rising Trend

This case of dating fraud seems to fit in alarmingly well within the current trend of deception we are increasingly seeing online. The recent Netflix scripted series Inventing Anna tells the story of a young woman from Germany who defrauded thousands by posing as a German Heiress.

And just last month, Netflix released a documentary about the ultimate fraudster Simon Leviev. For those unaware, he used various dating apps to find victims and defraud them out of thousands of dollars under the premise that he was a billionaire bachelor.

Noticing The Warning Signs

Thankfully, Samantha Cooper, founder of Rogue Daters Ltd. has tips for the rest of us. She's revealed the warning signs to look out for to avoid finding ourselves in situations such as these. Specializing in romance fraud, she works daily to help people avoid or even deal with financial loss and heartbreak.

As to why people catfish others on dating apps? She explained that it can sometimes be a matter of confidence and the belief that their matches would not be interested in the ‘real’ them. Alternatively, she explained, it could be an attempt to fraud people out of their money or control the other person’s feelings.

Moving Forward

Of course, there are plenty of people out there who are only looking for honest love. So while we encourage the use of dating apps, we recommend an eyes-peeled, guards-up approach to stay safe. Samantha recommended a basic online check on any potential date - searching for their name, place of work, or social media.

Samantha warned people to listen to their instincts when they feel something might be off and stressed the importance of knowing who they're dating. And finally, if we've learned anything from this story: we suggest avoiding any matchmaking suggestions from one's boss.