“The Obsession Behind the Smile“
Submitted: January 22, 2025
Author: Anonymous Entry

It was something out of a early 2000’s Rom Com, I was working an event when fate stepped in to make sure my path crossed with my soon to be boyfriend, Jake. He was different from any other man that had pursued me in the past, he was consistent and persistent in the most respectful and old-fashioned way. I wasn’t immediately convinced but with time and enormous effort on his part, he won me over.

It started innocently, or at least, I thought it did. My boyfriend, Jake, had been working with Gina for a little while. She seemed to be a bright, ambitious young woman—always quick to help Jake, always there. I didn’t think much of it at first; after all, it was just work. But the more I saw the way she would interact with Jake, the more I started to get a strange feeling. There was something in the way Gina became heavily invested in our relationship, the way she hovered and obsessively called him for things NOT work related, the way she always knew when I would visit him at work; even when she wasn’t there. How she was obsessed with meeting me when Jake and I first began dating. It wasn’t blatant, but it was enough to make me pause.

I tried to brush it off. Maybe I was just being paranoid, I thought. They had a professional relationship, and I had no reason to believe there was anything more. Jake did have a flirty nature about him naturally, and he did admit that when he was single, his loneliness drove him to have out of work relationships with some of his staff members. His transparency came after I made him aware that this was not normal behavior. He agreed, and stated he need to establish new and firm boundaries. No more blurred lines. Still, I couldn’t shake that nagging feeling because Gina was constantly injecting herself into our life. It was creepy and gave me obsession vibes. Plus, the fact she was known to have inappropriate secret relationships with her own boyfriend’s friends; well it didn’t leave much room for the respect factor, when it came to her morals.

One afternoon, I had a run-in with Gina that made me question everything. I was meeting Jake for lunch at his office when I walked in and immediately Jakes phone began to ring. Gina was watching us from across the road the entire time from her car. It immediately gave me chills to know she was still always somehow watching us. She gave me a tight smile when she saw me, but there was something in her eyes—an intensity, a quiet challenge—that I couldn’t quite place.

I didn’t say anything in the moment. After all, it was probably nothing. Jake and I left for lunch, and I tried to focus on the conversation, but that uncomfortable feeling stayed with me all day. It was like I was in the room, but I wasn’t really there. Gina’s presence loomed over us and the snarled smile from her yellow and black stained teeth remained ingrained in my brain.

A few weeks later, things started to shift in ways I couldn’t ignore. It began with little things—subtle, almost harmless. I noticed Gina started to heavily monitor and like my social media posts. At first, I thought, “Okay, maybe she’s just being friendly,” but it became a daily thing with her. Jake would tell me how daily she inquired on our relationship, to the point he was uncomfortable., “You two look so cute together, I hope Jake is treating you well!” or “You’re so lucky to have someone as successful as Jake.” At first, I didn’t mind. But then the tone changed.

“Jake’s lucky to have you. You’re so beautiful!”
“I’ve been there for him through a lot of tough decisions. I’m always just a phone call away if he needs someone to talk to.”

That’s when it hit me. She wasn’t just friendly—she was fixated. These weren’t casual comments anymore. She was trying to establish some kind of connection, some kind of ownership over him and oddly enough wanted to establish a relationship with me, so she could monitor our relationship from both angles.

I eventually removed her from all social media accounts. She is his employee, there is honestly no reason for me to have a personal relationship with this stranger. Thats when she did something that told on her true intentions. She immediately messaged Jake within hours of her removal asking him why I deleted her off my social media accounts; something that she would only know by obsessively watching my account. The heavy feeling in my stomach returned because I had my answer, she was cyber stalking both of us, but mainly me. She wouldn’t stop there, she would then make it her goal to know our daily moves by intertwining personal and work questions together.

I now realized how deep Gina’s feelings for Jake ran and it was becoming scary. She wasn’t just obsessed with him in a professional sense; she had blurred the lines between their working relationship and something more personal. She wanted him—and I could feel her wanting to make herself become a fixture in our world.

I confronted Jake about it, and while he was shocked, he admitted that things had been a bit… complicated between him and Gina. They had shared some private conversations throughout the year of their work relationship, and there were moments when he felt she was more emotionally invested than she should have been. But he didn’t realize how far it had gone. It wasn’t until Jake began to share more personal stories that he knew about Gina from others, that we both realized she was not the innocent young lady she proclaimed to be. She had a dark side to her, and attention in any capacity was her drug of choice.

“I’m sorry,” he said, his voice full of regret. “I should’ve been more aware of how I was acting and how she was perceiving it. I thought she just admired me professionally, but I didn’t see it turning into this. I will make sure she understands she is just an employee, nothing more!”

I could see the conflict in his eyes. He didn’t want to hurt her feelings, it was obvious she was inappropriate but he also didn’t want to lose me. It was a fine line, and I felt like we were both walking it.

The next step was clear: We had to set boundaries. I blocked Gina’s social media accounts, and I made it clear that I wasn’t comfortable with her behavior. Jake made it clear to her, that he wasn’t going to tolerate any more of the personal comments or interactions she tried to pursue with him & most importantly our relationship.

At first, she was defensive, even angry. She made remarks and tried to justify her actions by saying that she was only looking out for Jake, that she understood him better than I ever would. But I wasn’t having it. I told her firmly that I was the one he chose, and if she didn’t respect that, there would be consequences.

She eventually backed off, but not without a lingering sense of resentment. Things weren’t the same after that. While Jake and I worked through the situation, I couldn’t help but feel a little shaken. Gina’s obsession with Jake was slowly becoming an obsession with me. You know the saying, “Keep your friends close but keep your enemies closer.” Gina’s game was as obvious as an episode of Bluey. She wanted Jakes attention, she wanted to feel wanted by men. She had a history of struggling with low self esteem and seeking validation with men. She blurred Jakes genuine compassion as a manager into a fictional love story in her head.

The whole ordeal was not ideal for the start of a relationship but ultimately, it made me stronger. Jake understood how important it was to respect boundaries—not just with me, but with everyone he worked with and hopefully his future relationships. And I realized I had to trust my intuition and gut feeling, even when things got complicated. Because sometimes, relationships—whether professional or personal—can become blurry. But the clarity you create by standing firm in your boundaries is what keeps them from crossing the line.

The irony of it all is that within weeks of all this occurring, the company that they both worked for ended up going out of business. Some would say it was a coincidence, I would say it was Karmic Justice being served.