How I Cheated On My Girlfriends

Many of us consider cheating on your significant other a bad thing, especially if you are the one being cheated upon. I have been cheated upon twice. I know how hurtful it is, and its negative impact on trust. But that isn't the objective of this myTake.

The objective is to explore the roles of serendipity (i.e. chanced occurrence) and unplanned behaviours in dating cheating. The narratives place emphasis on facts (fictional names of the characters the only exception). The choice of basing each account on facts is to allow the reader to distill for themselves the moral aptitude of the protagonist (i.e. me) and whether each cheating event was avoidable.

I must caution, the cheating accounts are based on my own version of events, which may not necessarily reflect the accounts of the girls I cheated with and on. To keep the write-up short, many other factual details have been left out without compromising the overall account.

My First Cheating: When Two Friends Fell In Love For The Same Guy
Two girls (let's call them Jane and Lisa) who were longtime friends were hitting on me at the same time. Both girls knew the other had a crush on me, and none was willing to exit the race to win my heart. The competition between the girls was fierce. Each girl had her own supporters, wing girls and guys, plotting to outmanoeuvre the other. I'd be lying if I say I didn't like the competition.

Jane is outspoken, witty and brash with a tomboyish persona. She's the kind person who thrives on challenges and do things on her terms. Lisa is soft spoken and gentle with a gracious countenance. She generally would put her interest behind those of others, including her friends. But on this occasion, Lisa was determined to pursue her heart at the expense of her friend Jane.

For weeks I couldn't make a choice because choosing one over the other would make me feel really bad as I was friends to both of them. Realising my inability to make a choice, Jane stunned me with an evening musical concert ticket invitation (one for her and one for me). She knew I wouldn't say "no" as music plays a big role in my life.

How I Cheated On My Girlfriends?

After the concert, I accompanied her to her apartment. It's like she had choreographed every detail about my actions that evening: she knew I wouldn't leave her to walk home alone through that dim-lit footpath leading to her apartment. As you must have guessed, we made out that evening. I started dating Jane on condition the relationship should be discreet for a while out of respect for Lisa.

Few days after the start of the relationship Jane broadcasted to her friends including Lisa that we are dating. I was crossed by Jane's action, though I understand she wanted to protect her interest and to nullify Lisa's hope of forging a relationship with me. Lisa was hurt by by the news and I felt a sense of culpability. Though I liked Jane, my heart was consumed by the hurt I caused to Lisa. It brought me closer to Lisa; I bonded with her effortlessly than I did with Jane. I then made out with Lisa without Jane knowing.

I dated both girls simultaneously for about two months before ending my relationships with Jane and Lisa for the greater good of all three.

My Second Cheating: Sleeping With My "Dating Consultant"
She was 3 to 4 years older than me. She was really nice with me, and treated me in a caring, protective way. She was my go-to person when I wanted to bounce an idea about anything on dating, relationship with girls, etc. She understood me effortlessly than any woman I have ever met. She claimed it's because we are both of the same zodiac sign. [WTF!] She'd even tell me the girls I'm hitting on or hitting on me as if she was a clairvoyant.

How I Cheated On My Girlfriends

One evening I paid her a customary visit. After a while, we started kissing, and then had sex. I still can't explain how and why we got in that mood. She knew my girlfriend and I knew her estranged boyfriend. It has since remained our best kept secret.

My Third Cheating: A False Accusation Becomes Real
There was this girl called Pamela whose boyfriend had wrongfully accused me of having an affair with his girlfriend. The false accusation was widely known beyond our immediate friend circles. My girlfriend wasn't affected by the rumour but Pamela felt the need to visit my girlfriend to assure her the rumour isn't true. Pamela threatened to breakup with her boyfriend if he continues with the false accusation.

Three months after, I bumped into Pamela at about 6pm. She asked I accompany her to pick up a parcel. We then went to her place to chill and catch up with the latest in our respective lives. It began raining heavily as I was about leaving her place at about 9pm. Her house was located 1.5 miles from the main road. She had no umbrella. I had no choice but to wait for the rain to tapper out or stop.

Suddenly she appeared in her night gown, and told me she's about going to bed, however, she is living her main door keys and responsibility to switch off her TV and living room lights in my hands. The downpour mixed with thunder suggested I'd have to wait longer in her apartment. She suggested I should sleep at her place, and leave the next morning. She invited me to her room. We lied side-by-side and pillow-talked for another hour until we began playing the leg game.

How I Cheated On My Girlfriends

Suddenly, we started kissing. We recognised what we were doing is wrong. She then said, let's make the rumour to be real; after all, there are some people who believed the rumour. What transpired that night remains a secret. In some light, we merely acted on the script which had already being premiered in the court of public opinions.

My Fourth Cheating: Dating My Girlfriend's Best Friend
I still get ask how I managed to date my girlfriend's best friend under her nose for nine months without her knowing. My girlfriend had been telling me about her best friend (let's called her Nina). There was hardly a story she would recount without mentioning Nina's name. Even the outings I'd prefer to have only with my girlfriend would involve Nina. It reached a point I found the frequent mentioning of Nina in most conversations I had with my girlfriend annoying. Nina this! Nina that! Nina! Nina! [WTF]

I made a goal to recalibrate my relationship with Nina. As weeks past, Nina noticed I was cold towards her. She tried very hard to be nice with me—buying me gifts and inviting me and girlfriend for dinner. I began to see the good in her, and why my girlfriend loved her so much. I decided to reciprocate the warmth, caring, and pleasantry Nina has been showering on me.

Our improved relationship took an unexpected turn one afternoon at her apartment after a meal she had cooked for me. We began to make out. We acknowledged it was an unintentional mistake. The more we avoided each other the more the mutual attraction intensified.

How I Cheated On My Girlfriends

I was puzzled how a girl I hated was now sleeping with me. Equally, Nina couldn't understand why she was falling for her best friend's boyfriend. There was a time my girlfriend and I spent a night at Nina's apartment. Three of us slept on the same bed. I kissed, groped, and fingered Nina while my girlfriend was as sleep by me. A risqué adventure many would consider daring, offensive, or heartless on my part.

9 months after, I ended my affair with Nina—much to her despair. There was no way we could have ever made our relationship public at the expense of her best friend. I later rhetorically asked my girlfriend: If I slept with your best friend, what's the worst thing you could do to me? She replied with a question: why am I asking something that could never happen? Little did she know I was preparing her mind for the day the unfortunate cheating-with-her-best-friend tale would reach her ears.

Disclaimer: This myTake is not intended to glorify, condone, or promote cheating. I apologise if you have been negatively affected by this myTake.

Do you identify with any of the cheating events; if so which? Which of the four cheating events is worst, and why? Which of the cheating events would make a good script for a movie, and why?

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  • The last one because it was your girlfriends best friend you both crossed a line which should never have been crossed.