I was a serial cheater who had a string of affairs that devastated lives and ruined relationships. I’m not proud of my actions, but now, in my early forties, I am working hard to break this pattern of behaviour because I couldn’t live with the hurt I was causing.
It all started when my first boyfriend, Colin, was unfaithful. I was 17 and in love for the first time when I began to suspect things weren’t completely broken off with his ex-girlfriend. One night, Colin went around to pick up some belongings from the flat they once shared. I tried to call him because we had plans but he didn’t answer.
The next day, I confronted Colin about missing our date, and he told me he’d drunkenly had sex with his ex. He said it was a stupid mistake and begged for forgiveness. I said I forgave him but knew I would never trust him again. I was heartbroken and used his infidelity as an excuse to get my own back, and before long, I’d started an affair with a co-worker, Craig.
Craig and I regularly had sex over the next few months; it was thrilling and gave me an ego boost after the devastation of being cheated on. One day, Colin and I had a row, and I blurted out that I’d been unfaithful. He looked wounded; he had no idea. He started crying, and I felt terrible until I remembered he’d cheated first. I’d had my revenge and vowed that in my next relationship, I would stay faithful.
I lasted six months in a new relationship before getting drunk and sleeping with a stranger on a night out. That one night stand opened a floodgate. I thought, “I’ve cheated once; I may as well do it again,” and so I was unfaithful to my boyfriend a handful of times with different men. He never found out, but I ended our relationship anyway. I thought it was easier to cut things off before he got too attached to me.
I found it almost impossible to stop cheating. In a relationship, I made excuses to cheat that revolved around my partner’s perceived shortcomings. When I wasn’t happy, I’d seek pleasure from elsewhere, but the effect was only temporary; once the initial buzz wore off, I’d be left with shame and emptiness.
When I was single, I found myself seeking sexual gratification from people I knew were in a relationship and began an affair with a married co-worker. After three months, he told me he had left his wife for me, and I was horrified. I told him I had never wanted a relationship and assumed we were on the same page – our affair was purely sexual. He blocked my number and started calling in sick, quitting his job shortly after. His last words to me were: “You’ve ruined my life”, and I can still picture the anguish on his face as he said that, 20 years on.
I must have had around 15 affairs, some lasting weeks, others spanning months. I walked away from relationships I was in easily because I never let myself get close enough to get hurt. Often, my cheating was never discovered, but every affair made me hate myself a little bit more.
My most significant affair was emotional, not sexual. In 2018, while I was in a committed and monogamous relationship, I developed a meaningful connection with Matt, a friend of my partner. Matt had a girlfriend, and we’d often double date. While I wasn’t physically attracted to him, I loved spending time with him. We’d have deep chats over text that would last long into the night. He was the first person I spoke to when I had good news or a bad day. I trusted him with my darkest secrets and confided in him about the affairs. He didn’t judge and made me want to be a better version of myself.
One day, Matt called me with three words that shattered my heart: “I’m getting married!” I feigned excitement but felt sick. We hadn’t shared more than a hug, but I felt there was something more than friendship between us, and now he was making a serious commitment to someone else. I blocked Matt’s number because as much as I wanted him to be happy, I wished that he’d found happiness with me.
I broke up with my boyfriend and closed myself off emotionally after that, telling myself it was better to be alone than be hurt by anyone else. Which is ironic given how much hurt I had inflicted over the years with my affairs.
Sick of self-loathing, I decided to take a break from sex and dating for a year in 2019 to “reset”. Until I could commit to someone without the temptation to stray, I wouldn’t date at all. The pandemic meant that year stretched into almost four years of celibacy, and I felt great about it.
After the initial discomfort I felt when others weren’t validating me, I decided to focus my efforts on my career and nourishing my platonic friendships, which gave me much more fulfilment than sex.
In 2023, when I felt ready to start dating again, I began seeing a therapist. I told her I was a serial cheater and wondered if I was “fixable” and if I could ever commit to a long-term monogamous relationship.
She explained that cheating can emerge from complex causes like trauma and attachment issues, which can leave someone with a constant need for admiration and validation. Digging into my childhood, dysfunctional family dynamics may have played a part. My parents had favoured my brother over me, which had left me with feelings of inadequacy, low self-esteem and a deep fear of rejection.
My therapist told me I had difficulty finding love because I didn’t love myself. And the more I cheated, the more I thought I was unworthy of love. She explained that I needed to do some work to understand my impulses, emotions, and motivations while also showing myself some understanding and self-love.
The good news was I’d already started working on myself without realising. Taking a break from dating meant discovering my self-worth without a partner. I wasn’t a terrible, irredeemable person; I had made mistakes and wanted to change my behaviour. My therapist said that I might never be comfortable with monogamy and that I needed to work on communication with a new partner rather than resorting to my old behaviours of cheating or running away when things went wrong.
I joined various dating apps and explored ethical non-monogamy, which had become more mainstream since I’d last dated. It was refreshing to meet people who weren’t expecting to have all their needs met by one person. Instead of secrecy and sneaking around, there was honesty and clear communication.
I could date multiple people, but sometimes, I didn’t want to. It was odd. The confines of monogamy made me desperate to look for something outside of the relationship, but now I could date as many people as I liked; I had become selective. I became more concerned with quality, not quantity of partners.
Then something unexpected happened. I met James, who had never been faithful to a partner and was also in therapy. When we met, we were both dating other people. Over time, those other people drifted away, and we found ourselves just dating each other. Two people seemingly allergic to monogamy were now accidentally in an exclusive relationship.
We’ve been together for over a year. We’re both still in therapy, and we’re both still open to the possibility of dating other people. It’s the most honest relationship I’ve ever been in; when we’re attracted to someone else, instead of hiding it, we talk about it. Even though we sometimes fight, we don’t run away at the first sign of trouble.
Of course, I feel remorse for my past actions, but I’ve learned to forgive myself. I have no idea how this relationship will pan out, but for now, I love my partner, and he loves me. Most importantly, I now love myself, too.
