I always used to be quite amazed by people whom possess a somewhat cavalier attitude to sex. Hearing about the sexual accolades and escapades of friends and the broader public through various means of media I’ve always questioned the mindset of those whom partake in casual and non-committal sexual liaisons.

Being somewhat inexperienced in those early years of my involvement with women, I used to be very much the idealist. I used to wonder at what sense of satisfaction one could glean from a mere fling or one night stand. I used to look at friends of my own going on the prowl during the weekends and just shake my head in wonder. Things always seem so much more precious when they are beyond ones reach, and conversely all that of which is easily within our grasp is also more easily taken for granted.

This rule to me is really one of life’s basic fundamentals. For me personally, growing up with a low sense of self-esteem and confidence when it came to women, I used to look at women as beings who would always be above and beyond my grasp. And like anything beyond my grasp, my mind automatically made itself a promise to treasure and hold dear all whom somehow made their way into my hearts embrace.

It would be many years before this mindset would change, and so came another hurdle into my relationship with J. If we revisit the first sentence in this post, I will clarify that it sums J up to a T, though I assume many people whom are reading this would already have guessed that.


From memory, it was the near the end of the first year in our relationship where one aspect of our relationship started to skew off along a particularly awkward tangent. J was my second girl ever, in any and every way, and I was her…. god only knew what number I came on her list. The topic one day arose on how it was important for a person to settle down in life with the partner of their choosing, but yet have no regrets about their life up to that point.

Specifically, in conversation I mentioned that as a guy, of course it would be nice to have experience more than I currently have in the realm of sexual adventures, but it was by no means a necessity. Just as it would be nice to have driven a race car or gone backpacking around the world before starting a family. Would have been nice, but was by no means necessary.

J agreed and said she was glad that she’s basically gotten all the sex she’s ever wanted out of her system, and was now more than truly happy to settle down with me. Then things started getting awkward. She said she wanted me to have the same broad range of experiences that she had so I wouldn’t regret not doing them down the track. I told her those things weren’t important to me, sure it flies through my mind from time to time in passing, but it was by no means a big issue. And that was until she made it a big issue….

And now this is where our relationship, already choc full of bizarre twists, began to take another bizarre twist. She started to tell me that she wanted me to go sleep with other women because it would be good for me. And as much as I refused, she just kept repeating it. It all became quite awkward for me. I would say it was cheating, and she would tell me that it wasn’t because she was asking me to. She wanted me to go out to a club or what not, pick up a girl, take her home and have sex with her. And make sure that she never contacts me again, or vice versa. No strings attached sex was the aim of the game.

Now at the best of times, one would be correct in saying that this is probably one of the more awkward conversations that a couple are likely to have. Well, excluding those guys (some of my friends and colleagues) whom think that I’m probably the luckiest guy on Earth. Either way, I had no intentions or even seriously entertained the thought of having sex with anyone but my own girlfriend. And so I basically told her… “No”. I don’t want to do it.

Most people would have just dropped the topic right there and then, but J was no ordinary girl. She would bring up this topic again…. and again…. and again. Over the course of the next few weeks and months. In fact, she had started raising the topic at gatherings in front of all our friends!!!! In front of her conservative asian friends at that!!! I could see the shock on their faces when she kept telling me in front of them that we wants me to have sex with other girls, and repeatedly pushing the issue when I kept saying no. It was getting to be pretty fucking embarrassing and I could tell the other girls there didn’t know where to look, and some of the guys where having a great old time teasing me.

Eventually she stopped after many many months of this….. and little did she know just how much those actions would backfire on her.

It was I believe the start of our third year together that J had to leave for Korea on a 4 month long stint of student exchange or something. As part of her course, her and 4 of her close friends were going to to study at some University in South Korea for 4 months. By that point in our relationship, things weren’t too good at all. We were fighting and squabbling alot and I had spent much time questioning whether or not this would work out.

We did our best to maintain communication whilst she was in Korea but it was hard given her schedule, the price of phone calls, and the awful quality of the cheaper calling cards. With her and many of the good friends that I’ve known in Melbourne gone, only a few things kept me occupied and happy. Sydney, our dog that we purchased together. My job and the wonderful colleagues that I worked with. And my motorcycle…. which I purchased the moment the left for Korea. She never allowed me to buy a bike when she was here because it was too dangerous, so when she left, I made the most of that opportunity to both get my licence and a bike! Sneaky I know.

I also threw myself headfirst into a cell group at my church for the first time and made some friends through there. But most of all, the thing that kept me the most distracted during those months when she was away was that I met another girl.

Anne, an overseas student from Malaysia, was actually a girl that I met online and ironically, met through means that J setup just for fun. As I’ve mentioned many times before, self confidence was something I lacked when I moved to Melbourne. Part of what J did to remedy that was to setup a profile for me on some asian social site for laughs, to see if anyone would respond because she was sure they would. And respond they did. I surprisingly had quite a number of girls message me saying they thought I was cute or liked the photo that she put up there. I didn’t really respond to many of them at all, but they did serve the purpose of making me feel better about myself. Anne was one of these girls.

The Photo

When our relationship went down south even more so after J went to korea, because even with her away we still kept fighting over the phone somehow, I replied to one of the messages these girls sent to me. I was bored, I was lonely, and I was a little depressed. And so I replied to Annes message. We got talking over ICQ and and just had a great time talking as friends. We eventually met up for the first time and it was great. We both got on really really well.

Being with Anne just highlighted how much of a chore and just how taxing being with J really was. All the fights, all the abuse….. I started to wonder if she was the right one for me, and if she was the right one, how could she do or say all those things to me? How could I compromise on my values and beliefs so much? I had no doubt that I still loved her, but maybe that just wasn’t enough.

I could tell Anne was interested in me though it was more a feeling and vibe than anything she actually said or did. I thought back to J telling me all those months about how important it was for me to have sex with other girls, and how she wanted me to do it much to my reluctance. I thought about how I’ve never really had women show interest in me and now here was another one at my door. What if I wave by this opportunity only for my relationship with J to fail later, which all signs were showing it would.

And so I made a decision. I was going to break up with J, and I was going to sleep with Anne. I called J up and told her all about Anne and how I wanted to sleep with her. I told her all about what she had been saying to me the past year about sleeping with other women and that now I’m going to do it. But I will not do it while I’m still in a relationship. She heard my thoughts about how I didn’t think our relationship was going to work out with all the fighting that we were doing and all the personality conflicts that we had. I told her I still loved her but it just wasn’t enough. And so she broke down crying. She was begging me and begging me to stay with her. Telling me how she was sorry and she didn’t mean those things about me sleeping with another girl. That she can’t handle it after all and she shouldn’t have pushed me so hard.

It was too late. I said I am doing this, I have to do this. And that if we were meant to be, then we will still be eventually. But this is something I just have to do now. J begged me then to sleep with Anne if I must, but not to break up with her. I told J I was sorry, but our relationship was over.

And so I focused on Anne. The next time I saw her I was picking her up from her dorm. She lived on campus at Latrobe University. I’ve never seen Uni dorms before and it looked like alot of fun! Like something straight out of a B grade college movie! We then went to a party and I got to meet a few of her other friends, another of which I suspect may have been interested in me. She was Annes closest friend and just lived a few rooms down from her in the dorm.

After returning from the party it was quite late. Anne invited me up to her room and told me she first needed to get changed. She took her top off and told me she needed to remove her bra and asked if I could turn around. Now I’m no genius, but if a girl is comfortable enough to get partially naked right next to a guy she just met, even with his back turned, it was a pretty solid bet that my instincts were spot on that she liked me. She only had a single bed, but I did the gentlemanly thing and told her I’d sleep on the hard floor. She insisted, but I stuck to my guns and so woke up in the morning feeling pretty damn sore! She stirred when I woke and asked me again to slip into the bed where it was more comfortable. And that was when we had sex for the first time.

Anne was a great girl in many ways. She was smart, sassy, funny, and had a great body. But I could never imagine her as a girlfriend. The sex was good but in many ways still unfulfilling. We spent much time together but I just couldn’t push J from my mind. And I told Anne as much and that she understood. We weren’t boyfriend/girlfriend, we were just friends with benefits. I guess you could say she was my first ever fling.

As time went on, Anne kept hinting more and more that she wanted a relationship before coming right out and saying it, but I just told her I couldn’t, I was honest with her that my heart was still with J. She understood that. To this day Anne remains one of the most mature women I’ve ever known, and in the next chapter, you’ll especially see why.

My so called relationship with Anne finally hit a point where I just couldn’t do it anymore. I told her straight to her face that I really cared for her, but I just couldn’t give her what she wanted and that it was just not fair to her. I truly cared for and loved her as a friend, but unfortunately no more. As much as I tried to get rid of it, J still had a complete hold over my heart even though I wish it would be otherwise. Anne smiled in understanding, said J was very lucky, and just told me to follow my heart. I know she didn’t agree with me as she knew about how J treated me, but she just wanted me to be happy. And for that I truly admire her.

And so I went home, picked up the phone, and put a call through to Korea…….