The Worst Man I’ve Ever Dated

The red flags and why I stayed

I’ve dated some men that have been “the worst” in ways that are comical and lighthearted. You know the stories that leave people in long-term relationships with a renewed sense of love for their partner? These are dating experiences that would make great material for stand-up comedy, or at the very least, that are sure to entertain our friends.

Experiences of wild incompatibility and mismatched expectations, or perhaps the infamous ghost, are ones that most of us have first-hand experience with. They are undoubtedly unpleasant to experience but they are an avoidable part of dating for most of us.

This is not one of those stories.

There is little to laugh about when I recount the worst man I’ve ever dated. For some folks, this article may be one they wish to skip and I completely respect that. This story contains depictions of abuse in an intimate relationship so please take care.

If I were a psychiatrist I might be able to say that this man had Narcissistic Personality Disorder but I’m not, so I’ll skip the diagnostic label. Instead I’ve decided to call him “the worst man I’ve ever dated,” and that feels about right to me.

The beginning: attraction + fear

I don’t actually believe the worst man I have ever dated is a lesser person than me. A therapist once told me that “we attract the people who are at a similar place in healing from their trauma that we are.” At the time, I was dating this man. Hearing that I was similar to him in any way was infuriating.

I was attracted to him, though. There was something about him that drew me in. I can blame it on charm and trickery—that I was manipulated—but the initial spark was more organic than that. I remember sitting across from him at the table the first night we met and letting that attraction override any sense of doubt.

He was passionate about his beliefs and there was an intensity to him that was equal parts intimidating and intriguing. I’d never met anyone like him before and that left me bewildered and curious. I wanted to figure him out and I wanted to give him a chance.

He didn’t trick my intuition, though. I knew on some level that something was off and that I should probably walk away. I think I also knew that if I stayed too long he would hurt me. If I followed him to live in another country, as he wanted, I am almost positive I would’ve been trapped in a dangerous situation.

It wasn’t until I read Gavin de Becker’s book called The Gift of Fear, almost 2 years after the relationship ended, that I gave the fear I felt when I was dating him the credit it deserved. I was afraid because he was dangerous. I was attracted to him but he also scared me in a way that no man I’ve dated ever has.

In the words of Gavin De Backer:

“Intuition is always right in at least two important ways;
It is always in response to something.
it always has your best interest at heart”

Our beginning was a combination of fear and attraction. In retrospect, I am not sure I could really pull the two apart. It was something that I was swept up in and it left me changed.

So what makes him the worst man I’ve ever dated? Looking back now, these indicators of him being the worst could’ve also been considered warning signs if I’d been open to seeing them.

His past was sketchy

In the early days of our relationships he told me stories about his past that made it clear he had a history of not only disregarding the law and “the system”, but of a complete disregard for his partners’ boundaries. I thought that since he was being honest and transparent it must mean that he has changed. Why else would he be so honest?

He told me early on that after a breakup with a partner he lived with, he used the key he still had to sneak in and bug the apartment so he could listen to what his ex was doing. He told me about how he discovered she was dating someone else. At one point he even confronted the other man. The most disturbing part of listening him recount this story is that he didn’t seem to believe he had don’t anything wrong. He was an excellent justifier (even if he was the only one he was convincing of anything).

If I am being honest, this story was chilling to me. It made me nervous that he knew where I lived and I remember feeling a deep sense of regret for inviting him over to my house. Although it may have been a red flag to walk away, it also made me realize walking away might not be as easy as it should be. I was afraid if I walked away he might not want to let go.

This was just one of the many stories of his past that set off internal alarm bells. He told me—time and time again—that he did not respect authority or his previous partners. His values clashed starkly with mine. My gut was screaming at me the entire time but I refused to listen.

He would make fun of me

I remember this one moment with alarming clarity. It was a dreary, overcast day and we had forced ourselves outside for a run to get some fresh air. At one point, we raced up a hill. He beat me to the top.

Later, I jokingly tell him that I would beat him in a race on bikes. At the time, I was getting into road cycling and I can say with the utmost confidence I would’ve been able to bike up a hill faster than someone who, at the time, didn’t own a bike. Not that it matters—I was joking.

A switch happened in him, very suddenly. His voice lowered, there was flick of fury in his eyes and he looked at me seriously and said something like, “are you fucking kidding me? Did you not see how you ran up that hill?”

He was not joking. He was angry.

I had offended him. It was in that moment that I realized just how fragile his ego was. He could not take a joke and in return, he had to cut me down by insulting me. I could not be better than him at anything. I had sensed this before but this particular moment made something clear: you must let him have the power, otherwise, he will snap.

Another time he had picked me up in the morning to drive me to work. He worried about me biking in the rain. I had put on some makeup that day— a bit of concealer and some cream blush. Blush and under-eye concealer—my go-to combo when I wore makeup. He looked at me, scoffed, and said, “you look like a clown.”

I tried to laugh it off but it stung. Why would he say something so cruel? I can look back now and see he was trying to make me feel small. Every jab a reminder of my place in our relationship. I, like many, can appreciate banter in a relationship but this was unlike anything I’d experienced before. He was mean.

He made me feel stupid

This guy may have been the worst man I’ve ever dated but he was also well-read. He had a sharp memory and could regurgitate “facts” and stories under pressure and on a whim. He knew what he wanted to be right about and he knew those topics well. You could say he might have been a pseudo-intellectual (though, he would prefer to think of himself as a “passionate intellectual.”)

I noticed since I left the relationship I’ve had an insatiable hunger for knowledge. It is almost as if I don’t want to get caught like that again. I want—I need—to know things. I know, he sounds awful, but I can’t help but look for the ways he changed me. I see this as one

I want to understand how the world works. He wanted me to hate the world just as much as he did so he could save me from it. He was a conspiracy theorist who was filled with hate—and the conspiracies gave him an outlet for it.

He would frequently leave me feeling stupid during our conversations. He held opinions with fierce conviction and if I ever said something to contradict him—he would laugh at my ignorance and tell me how wrong I was.

I remember when he smacked me across the face and I reacted with shock and horror he laughed and said, “I was just joking. I did the same thing to my ex-girlfriend and she could take a joke. Why can’t you?”

Wait, what? I was stunned. I don’t remember what happened after that but I know I ended up walking up the stairs to his apartment. Nothing I said could convince him that what he did was wrong. He was never wrong. If he was never wrong it meant I was the wrong one and this dynamic often left me feeling insecure and well, stupid.

Things moved way too fast

This is one of the warning signs that de Becker talks about in his book The Gift of Fear. In his words the warning sign is this:

“At the inception of the relationship, the man accelerated the pace, prematurely placing on the agenda such things as commitment, living together, and marriage.”

There was part of me that relished in this. Finally, a man who isn’t afraid of commitment and who could talk about the possibility of marriage and kids. Seeing as I had a track record of dating avoidant folks , this came as a welcome relief.

I also sensed that he thought he could move in with me within our first month of dating to avoid finding a new place to rent. This was far outside of my comfort zone and I quickly shut this down. I am almost positive if I hadn’t asserted this boundary early on, he would’ve happily moved in.

He had a dream to buy property somewhere and disconnect from the society he had come to blame for all of his problems. There was something appealing about this idea. There was also something about how early in the relationship he talked about these things didn’t feel right. I still look back am feel overwhelmingly relieved that I didn’t give in to his desired pace of the relationship.

Why did I stay?

When we read about “red flags” we assume that if we ever came across them that we would leave. I know I always thought I would. Even before I saw the red flags clearly, my intuition was urging me to run. I had all of the information I needed to know he wasn’t good for me yet I stayed for 6 months.

I still don’t have a clear answer for why I stayed. It has taken me over 2 years to be able to think about it enough to write about it.

I am extremely lucky that I wasn’t tied to him financially and I didn’t share a home with him. I was also extremely lucky that he had a plan to leave the country—one that I believe he followed through on. This allowed me to leave him safely because I knew he would be thousands of miles away in the weeks following our breakup.

Maybe I stayed to stay safe. I doubt it was a coincidence that I ended things with him only days before he left the country. He knew where I lived and even though he terrified me in many ways, I felt safer with him believing he loved me then I did with him angry with me. I stayed for many reasons I told myself but more than anything, I stayed out of fear.

There it is. The story of the worst man I’ve ever dated. In a way I am grateful that he came into my life because he taught me why people stay. I’ll never again judge someone for staying in an abusive relationship because I understand in a way I’m not sure I could’ve understood had it not been for lived experience.

I’m grateful that he taught me to respect and listen to my fear. He taught me the importance of boundaries and asserting them with conviction. Maybe this gratitude is just part of me trying to make sense of an otherwise really dark and sad 6 month period in my life.

When I reflect on my time with him it is hard to imagine that it is me who was with him. Writing about this has felt a bit like opening up this part of me that I tucked far out of sight and shut the door on. Behind that door the fear is still present—searching for him in men I walk by on the street and looking behind my shoulder when I’m walking alone at night. I just hope that by opening the door I can let the fear seep out and leave my body, once and for all.

I’m just trying to learn as much as I can when I’m here. I also like to write about it. I write mostly about love, relationships, attachment, and consciousness.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store