6 Important Lessons I Learned When I Dated a Serial Cheater
In 2019, I set out to go out on fifty first dates. I was newly out of a two-decade marriage and wanted to take myself on a dating adventure. I went in with zero expectations except meeting new people and having a good time. If I found love, that would be a bonus.
My dating escapades are chronicled in my memoir Fifty First Dates, and on my podcast of the same name.
The experiment turned out absolutely nothing like I thought it would.
When I’d dated before marriage, the kinds of boys and men I was with were from a fairly narrow spectrum. I’d met every single one of them in school; high school, college, and graduate school. They were exactly like me, middle class or well off with professional parents. The wide world of dating apps was a completely different assortment of people. It was my first introduction to men with secrets lives.
The last man I dated (before COVID brought my dating experiment to a grinding halt) was the first man out of fifty plus who actually pursued me. What I didn’t know at the time was that Carl* was an expert in the art of pursuit. This leads me to the first thing I learned.
1. Serial Cheaters are masters at the art of pursuing women.
Why? Because they have to be. Imagine the game a man has to have to convince a woman to be his side chick. Carl had enough charm to spare. Even after he’d won me over, he couldn’t help but be disappointed in the women he hadn’t ‘gotten.’ Once while we were walking on the beach (cliche, but it is Southern California), he was griping to me, upset because his business partner hadn’t set him up with every eligible woman she knew the week his wife finally walked out on him.
Another time, Carl was amazed his brother hadn’t found a date in his singles-laden apartment complex. Carl had an intense fear of dogs. But he insisted that if he’d lived in his brother’s place, he would have gotten a cute pooch and would have actively pursued all the dog-walking women. In his opinion, his brother was wasting all those prospects.
He had a lot of stories on how he’d successfully pursued women because it was the primary focus of his daily thoughts and activities.
2. Serial Cheaters are liars in other areas of their lives.
I’m sure you’re wondering how I fell into a relationship with a serial cheater. For a long time, so did I. The best and truest answer is that Carl obscured facts or straight up lied about his past when it suited him. He was almost divorced, he said. Translation: his wife had left him a few weeks ago, but they were still…involved.
Carl lied about being a smoker because, as he admitted, I wouldn’t have agreed to a date with him. He lied on his taxes (he was audited — Karma exists). He lied about having a Master’s degree. He would have lied to get his broken window replaced for free, but he forgot to tell that lie in time. At the end of our brief journey together I watched him in real-time to try to calibrate his lies to what he thought I wanted to hear.
3. Serial Cheaters are never to blame.
The thousands of words Carl dedicated to trying to explain away his cheating were legendary. His wife was to blame for his first affair. He actually said she didn’t want him to find true love and was blocking his way with her objections. His in-laws were to blame. His kids were to blame. I flat out asked him if he took responsibility. His answer, ‘no.’
4. Serial Cheaters gather enablers.
When Carl told me his mother helped him cheat, I was…appalled. Honestly, that one was a surprise. She paid for plane tickets so he could see his first mistress. His mother held his phone for him so his wife couldn’t trace his movements. He rallied his family around calling his wife a ‘bitch’ and ‘self-centred’ so that he could garner sympathy for being truly put upon one. Surprisingly, to me at least, they supported him.
5. Serial Cheaters don’t like women.
Carl claimed to love women. Claimed to be a champion of feminists and feminism. All the dancers in his favourite West L.A. strip clubs loved him because he was different from those drooling caveman-like specimens around him.
The digs against women started subtlety. First, it was his crazy bitch of a wife. Then he wanted to know why women who had ‘muffin-tops,’ between their shirts and jeans didn’t stay inside. Next, he sent me too many texts on how his female business partner was getting fat and therefore unattractive to his male gaze. Then it was me. He was surprised I was comfortable being naked. It was his last time getting that view.
6. Serial Cheaters don’t change.
Carl claimed I could tell he was honest because he’d shared he was a serial cheater. Other men on dating apps proclaimed the same. Weren’t they so up front when they told me they were married? One long winded email claimed he would never cheat on me because I was perfect. I didn’t stay long enough to find out if he’d cheat with another woman, because he was too busy ‘cheating’ with his wife. Separated was not divorced. Moving out was not moving on. When he told me his garage dwelling tenant wondered who was his wife and who was his girlfriend, I took the hint and walked away.
No amount of charm was worth the angst. She’d had twenty-four years of him and I was happy to leave her to it.
I was still in my cool girl phase when I was dating Carl. I thought I had to be open and loving and a giver of the benefit of the doubt and second chances. I believe the universe delivered Carl to me for a reason. It was to learn the lesson that I shouldn’t lower my standards or let someone breach my boundaries.
Lesson learned.
Carl’s name has been changed to protect his privacy. Jolie Moore is a romance author and the host of the podcast Fifty First Dates. You can subscribe to her weekly newsletter here.
6 Important Lessons I Learned When I Dated a Serial Cheater was originally published in Relationship Stories on Medium, where people are continuing the conversation by highlighting and responding to this story.