3 min

I Dated a Psychopath

I would never wish death on anyone. But if I found out my ex was dead I’d be relieved. 

For seven months I was in a toxic relationship. At best, he was manipulative and narcissistic. At worst, he was a psychopath.

One day we were walking to dinner and Jon was boasting that he would thrive in an apocalypse.  He nonchalantly added, "I'd love to kill someone with my bare hands." 

A red flag waved in front of my eyes but I pushed it aside. He was only joking, of course. And I loved him.

I’d fallen in love with Jon so fast. At the beginning he made me feel like I was everything he’d been searching for his whole life. He showered me with adoration and assurances and very early on spoke of marriage. It felt too soon for marriage talk but I reveled in it. I loved how much he cared for me and had no reservations about us.

But he slowly started to test his boundaries and say hurtful things like, Why can’t you be more like ____? Fill in the blank with any number of my girlfriends. When I reacted with surprise or hurt feelings he said he was just joking. He smiled that charming smile and my hurt quickly turned into affection.

He talked about our wedding and our future so easily and naturally. But when I brought it up he said, "Woah, getting ahead of yourself, aren't you?" 

Jon said he was who he was and I should not try to change him. He told me I was the one who needed to change. He said I needed to be a better girlfriend, needed to lighten up, and needed to be more supportive of him.

It was a while before I realized he acted differently towards me when we were alone than if we were with people. Alone, I didn’t think he even liked me. With people, he couldn’t keep his hands off me and told everyone, "Isn't she the best?"

One night we were heading to his friend's house for a party. We got into an argument. The argument continued as we were walking up to the house. As soon as we reached the front steps his whole demeanor changed. He was happy and calm. He turned to me. "Ready?" With a big smile on his face.

I was not ready. I was pissed. And confused. Who are you? We entered the house and Jon wrapped an arm around me. He projected this image of us as this in love, happy couple.

And I believed it.

While I was sure Jon was the person I was going to spend the rest of my life with, one aspect of our relationship was troubling. I said to my girlfriend one day, "Our relationship is perfect. I love him so much... but the sex isn't great."

The sex was horrible. He didn’t care about me. It was all about him. He’d quickly cum, then jump out of bed happy as could be.


And I was lying there thinking, What about me? 

When I finally addressed it he told me I was the one who wasn’t normal. He said his ex-girlfriend never cared about getting off. Why should I?

He also made me feel bad for not giving him more blow jobs. So what did I do? I watched YouTube video tutorials and read articles on giving a good blow job because I was so scared of losing him. I gave him more blow jobs. All the time. And when he went down on me - which was hardly ever - he made a face when he got down there like it was disgusting. Like I didn't shave well enough. Like it was my fault he didn’t want to be down there. Like I was less than.

I wanted so badly for our relationship to work. I turned to my friend Bobby for help. Bobby was happy to give advice. He told me I needed to lick Jon’s asshole.

Excuse me?

He assured me this would work. "Jon will fucking love it. You can't be shy. You gotta just flip him over and get all up in there."

Ew. That sounded gross and completely out of my comfort zone.

But of course, I did it. Because I had been brainwashed into thinking he was amazing and we were going to spend the rest of our lives together and it was up to me to make it work. I couldn’t be selfish. Jon told me that all the time.

The night I finally did it was after we had a fight and Jon had the nerve to call me vanilla. I was so mad that I flipped him over and I licked his asshole.

It wasn’t as bad as I thought. I would even consider doing it again with a partner who actually loved me and made me feel safe. I'm all about experimenting and trying new, fun things in the bedroom. But Jon said nothing afterwards. He didn’t say, "That was great," or "I can't believe you did that," or ANYTHING. No appreciation, no recognition. Nothing.

The relationship was crumbling. But Jon didn’t break up with me. He just started to play the victim and said how he “always runs from a good thing.”

I hate how pathetic I was, how I pleaded and tried to hang on. I said we could work on it, we could get through anything. He didn’t tell me no and he didn’t tell me yes. He kept me dangling until I felt like I was losing my mind. I finally demanded an explanation. He answered the phone and talked to me as if he had already ended things and I should stop being crazy. And obviously, he still wanted to be friends. 

It was at this moment I saw him for who he was. He didn’t actually care about me. He just wanted everyone to think he was a good guy. I yelled that I never wanted to see him again and we would not be friends, and I hung up.

After two months I made an appointment with my therapist. I hadn’t seen her in a year. I cried as I told her everything and it was she who gently let me know I was dating a psychopath.

The word “psychopath” was scary and it jolted me. A psychopath?

And so began my deep dive into psychopathy. If you think you might be or might have been in a relationship with a psychopath, Psychopath Free by Jackson Mackenzie is a must-read. 

Mackenzie described exactly how I felt towards the end of the relationship:

“Your natural love and compassion has transformed into overwhelming panic and anxiety. You apologize and cry more than you ever have in your life. You barely sleep, and you wake up every morning feeling anxious and unhinged. You feel insane, exhausted, drained, shocked, and empty.”

I felt all those things. And as I read the book I felt a lot of shame. I never thought I'd be the kind of person to let another human use and manipulate me. But the more I learned about psychopaths the more I learned that my susceptibility to him was because I was an open, loving person. That was not something I ever wanted to change. But now I am equipped to see the warning signs; particularly, gaslighting. It felt horrible to realize I’d been duped. But it was freeing to come out on the other side a stronger person.

It took four months before I finally blocked the psychopath on social media. I did a lot of soul searching and self-care. I moved to a different city. I spent time with my girlfriend and her two little boys - kids have a magical way of keeping you present. I focused on what brought me joy and surrounded myself with close friends.

I hate that I still think about Jon. I don’t want to say I’m afraid of him, but sometimes when I walk into a dark room I imagine him lurking in a corner.


Much thanks to Adam Tank and Sam Bleecker for feedback on this essay.