I CHEATED: Cheating On My Boyfriend Was The Best Thing I Ever Did

I always swore I would never be a cheater, but I find myself looking back on my infidelity with no regrets.
Publish date:
May 21, 2015
infidelity, cheaters, I Cheated, Break Ups

There’s no way to make this confession without entirely vilifying myself -- and the truth is, there’s no justification in the world for what I did. Cheating is wrong, period. I won’t pretend that my actions didn’t have severe consequences.

With that said, I would do it over again in a heartbeat.

I met my (now ex) boyfriend, Jay, while I was still in high school. To protect his identity and my own, I won’t reveal the exact circumstances of our meeting -- but our relationship was innocent for several years, particularly in light of the 11-year age gap between us. At the time, it felt like a very safe friendship -- I knew his family, and our parents had been friends in college.

I was intrigued by his vast knowledge (he’d had multiple careers), and his many interesting hobbies. I was curious about his motorcycle, and he gladly took me on motorcycle rides -- eventually teaching me to ride on my own. He began tutoring me occasionally after school, and I began to harbor a lingering crush. (It didn’t help that he was also tall, blonde, and handsome).

The college years came, and my connection to Jay mostly fizzled, though he would occasionally email to see how I was doing. I started dating another student my first year, but the relationship turned sour after a few months. I’d fallen head over heels in love, and the fallout from our dying relationship was equally dramatic and spectacular.

I feared for my safety after we broke up. It had been my first real relationship, and the emotional aftershock felt devastating.

Out of desperation, I contacted Jay and asked his advice. He had always offered an objective perspective on any of my problems, and I knew he would help if he could. True to form, he provided some excellent guidance, and listened while I vented and cried. When I needed an escape, I would text him and he would drop everything to come pick me up and drive around aimlessly. I viewed him as my rescuer.

Predictably, I started to feel very attached to him, and was surprised when I realized I was feeling an attraction that went far deeper than my childhood crush. He was far older than I ever would have anticipated dating at the time, but I felt safer in his presence than I did with anyone else.

I slowly began to suspect that the feeling was mutual; he would drive slower than normal when taking me home, and texted or emailed me often throughout the day, though he was never flirtatious. Despite his coolness, I knew our relationship had turned into something more.

Things happened quickly after that. My relationship with my family was strained, and I eventually began staying over many nights a week at Jay’s place, though we were not sleeping together. He eventually offered to let me stay indefinitely, and I jumped at the opportunity.

The arrangement seemed perfect for a time. Jay continued to be sensitive, fun, and a great conversationalist. I continued going to school, and took a part-time job as a waitress at a local restaurant. We got a puppy and started talking about our future wedding.

Then the doubts began to slowly creep in. In spite of his assurances that he just wanted to take things slow, I felt there was a distinct sense of separation between us.

One of my first indicators that something was wrong happened the day we left to go on a vacation with multiple members of his extended family, including his parents. He told me before we left to “not act like we’re a couple,” and “definitely not admit we’re living together.”

While his family was wonderful, and appeared to welcome me with open arms, the questions became awkward. His brother asked me outright one evening, “What’s going on between the two of you?” I squirmed and hedged, finally telling him it was probably best if he asked Jay, who continued to refuse to acknowledge our relationship.

And things were strange behind closed doors, too. Despite being in his mid-thirties and having had several girlfriends in the past I knew of, he claimed to be a virgin. The most he would allow was kissing, and he refused to see me with my clothes off -- going so far as to demand that I remain at least partially clothed at all times.

I began to feel horribly undesirable, though he would assure me I was attractive, and I felt he was being honest. I had also never experienced a lack of male attention based on my looks, so his lack of interest was baffling. Because I felt such a deep attachment in other ways, I decided that I could forego the physical side of our relationship (for a while, at least).

I foolishly expected things to change, but three years went by -- and sex was still not on the table. When I would ask when he might consider exploring that aspect of our relationship, he would answer “when we’re married.”

I felt satisfied with his reply for a time, but quickly realized that he had no real intentions of getting married anytime soon. He admitted that his last relationship had ended for the same reason; he wasn’t sure if he ever wanted to be married, and was almost positive he didn’t want children.

I felt blindsided by the admission, and also mislead by the many conversations we’d had about what our future would eventually look like.

Our relationship finally fell apart when I discovered he had been having an emotional affair with another woman. There were strange disappearances -- long trips to the grocery store, or nights spent late at work -- and long conversations into the night via instant messenger, which he refused to let me see.

An email left open on his computer eventually confirmed my suspicions, and my trust was broken. Despite the obvious (and irrefutable) evidence that he had been unfaithful at the very least on an emotional level, he staunchly refused to admit that he’d done anything wrong. He convinced me to stay, promising that he didn’t realize his actions had been out of line with what I considered acceptable in our relationship, and promised to do better.

Stupidly, I stayed. But I quickly realized that there was no going back -- I couldn’t look at him the same way, and began catching him in other lies.

While searching for vacation photos on his laptop, I discovered a folder of images saved from facebook -- pictures of my friends in bikinis and revealing clothes, and some of ex-girlfriends from years ago. He promised to delete them all, but I found them hidden (badly) in another folder a couple of weeks later. I also discovered that he’d been emailing women via a dating site pretending to be me, which only confused me further.

We began sleeping in separate bedrooms and spending long hours outside the house. We were politely civil to each other, and there was the occasional attempt to go on a date or rekindle some sort of romantic feeling, but the wood was wet.

I was afraid to leave -- afraid to start my life over, financially and emotionally. There was just too much invested, and I found it almost impossible to untangle myself. It sounds silly in retrospect, but I couldn’t bear the idea of leaving my dog behind, and I also knew it would be near impossible to find an apartment within my budget where I could have a big dog. I cried myself to sleep every night, and felt like I was barely dragging myself through the days.

Then I met Scott (not his real name), the love of my life, and everything changed. Our first conversations were friendly -- nothing more -- but I immediately felt the twinge of butterflies in my stomach that I’d forgotten existed. He was incredibly handsome, but beyond that, he seemed genuinely interested in my life and what I had to say. He made me laugh, and I felt relaxed and at ease for the first time in months. He asked for my number, and I gave it to him.

I didn’t fall in love with him in those first days, but I realized that I could. I was reminded that there could be so much more within a relationship than what I’d grown accustomed to with Jay. There was potential out in the world -- and if not with Scott, then with someone else. I could fall in love again.

I could be free of the toxicity that my relationship with Jay had become -- something that was dying, and only sapping my emotional energy. I knew it was truly over. All that was left was the final conversation.

I slept with Scott after the first full day we spent together, and for the first time in years, I felt truly loved and desired. While I laid in his arms afterward, I was surprised that I felt no guilt. I had been absolutely starved for a feeling of connection, and expressing myself physically had felt like the most natural thing in the world.

I went home the next morning and told Jay that I was leaving. I was moved out by the end of the day. I never told him that I slept with someone else, and I’m not sorry for keeping it from him. It would have only caused him pain, and I saw no purpose in confessing to ease guilt that I didn’t feel. He asked if he should wait for me, and I told him that I wouldn’t be coming back.

Scott and I are still together, and we have a beautiful partnership -- built on honesty, trust, and the mutual meeting of needs. While the beginning of our relationship was unorthodox -- and not at all the fairytale I might have dreamed of -- I have never regretted giving my heart to him.

I may not have done the right thing, but I did the best thing I could have done for myself at the time. That’s enough for me to live with no regrets.