I CHEATED: I Cheated on My Boyfriend of 6 Years with Our Best Friend

Yes, I cheated on my boyfriend. No, I don’t regret it.
Publish date:
May 27, 2015
relationships, cheating, self worth, infidelity, cheaters

I met Steven* when I was 15. He found my screenname in a list of others who viewed my best friend Phillip’s AOL Instant Messenger profile. He sent me a message, I replied, and two weeks later we met at a park where he did LARPing (Live Action Role-Playing) with foam swords and shields.

He found me awkwardly standing at the top of a hill, my mom playing spy sitting on a bench behind me with sunglasses. It was my first sort-of date and that day sparked what would be a 6-year relationship.

Steven was always a bit on the heavier side, preferring Mt. Dew and Taco Bell over most other foods. I remember having a moment on our second or third date when he approached me in the movie theater, “Is this boy really my boyfriend?” It held within it all my girlish dreams of having a boyfriend and a bit of harsh judgement. Was I really attracted to him? Or to the idea of being in a relationship?

Steven and I dated throughout all four years of high school until the fall semester of my Junior year of college. Three months before I broke up with him, on Skype, thousands of miles from home, sitting on my bed at my homestay in England, I cheated with our mutual best friend, Phillip.

Phillip and I grew up together and he sensed how unhappy I was with Steven. He even insisted that the reason Steven and I couldn’t have sex was my lack of interest in him physically. (Vaginismus ended up playing a huge role, but that’s another story.)

One warm evening at the end of May, Phillip and I were texting about my unhappiness and I felt myself typing, “What if we got together?” By the time I realized I hit send, he replied with “I’m on my way.” We kissed in my bedroom and it was nerve-wracking and guilt-stricken and… incredible.

In that moment, I had never felt a kiss could be so powerful. Over the next few months, Phillip and I would meet, talk, and, while we never had vaginal intercourse, participate in other sexual activities. I found myself falling hard while Phillip kept pulling me in and pushing me out.

He said even if Steven and I broke up, we could never date, yet I hung around, thirsting for satisfying sexual experiences and hoping he would come around to loving me too.

I left for England to spend my Junior year abroad in September of that same year. Steven had been through a lot of family complications that summer and I just didn’t have the heart to tell him anything. I told myself I’d break up with him over winter break, when I was home and face-to-face.

That was the plan, until one weekend trip to Ireland, anyway. My girlfriends and I ran into a group of boys on our bar tour. One of them I ended up making out with that night and the night after. I couldn’t do this anymore.

As soon as I was back in England, to my laptop, I Skyped him and did the cowardly thing of asking to “take a break.” The last thing I wanted to do was hurt him, which is why it took me so long to act to begin with. He fell silent and I could see through the screen that he was starting to cry. I decided this was hard enough and never told him about Phillip or Ireland.

Things began to grow awkward. He still went to Thanksgiving at my mom’s house, even with me being in England. He still insisted on being at the airport when I came home and taking me to a local hockey game. I don’t know why I permitted any of this. Maybe it was the guilt.

By the time I left to go abroad again, it was officially over and I was signed up for OKCupid. (My high school friend insisted I try it.)

From January to June, I had all kinds of wonderful and amazing experiences. I traveled to the Arctic Circle, drove a dogsled, lied on a beach in Mykonos, and had an incredibly magical, romantic night with a French boy returning from Estonia.

As time went on, I began to realize how suffocating my relationship was with Steven. He would cry and plead with me to not leave if I ever got upset with him. He tried asking me to marry him as if by proposing to me, I’d forget about my dream at the time to teach in Scotland and stay in the US. He would tell me I was a “fun-sponge.” We never did anything sexual because I wanted to, but felt I had to as a girlfriend even thought I felt nothing sexually for him.

I started dating other people, some cool, some not-so-cool. Phillip and I ended up becoming “fuck buddies” after I returned from Europe. He said he’d help me get over my vaginismus, but it never worked. Most of my life, I considered Phillip to be “The One that Got Away,” but I think it was more “The Best Friend Who Manipulates You Into Sex Without Actually Committing.”

When I started my senior year back in the States, I met Jamie, my current boyfriend. Jamie, through a weird string of coincidences, was in the same club as Steven in our large 35,000 student university.

When Steven discovered I was dating Jamie, he grew angry and depressed. I heard stories from friends, who would see him turn to alcohol in destructive ways, from sleeping in his car passed out drunk in the middle of winter to the bottles upon bottles of beer that apparently piled up in his room.

One night, at a huge party we both attended, he asked me to come outside with him and led me to the dark side of the building. He grew upset and said he never wanted to be my friend and I was to ignore him at places like this. He told me to leave and I never saw him again.

While I’m not pleased with my actions, I don’t regret them. My cheating, it turns out, was the only way to force myself into seeing how unhappy I had become.

By the time I met Jamie, I was in a healthier state of mind and realized what goes into a positive relationship. Jamie helped me slowly recover from my vaginismus and I FINALLY had vaginal intercourse and it was AWESOME.

We moved in together and have two cat babies of our own. I have new dreams now of traveling and writing. I started an MFA program in Creative Writing and Jamie encourages me to do what makes me happy. I learned to love myself and, in doing so, to love another person with my whole being. I just had to take a few detours to get there.

*All names have been changed