My sister and I were dating the same guy...

Sit down and buckle up, do I have a journey for you.

I have been single for majority of my adult life. This use to be something that I despised, thinking that the status of ‘single’ defined me as someone ‘unworthy’. It has only been in the last three years of my life where I realised that the ‘status of single’ is not something negative at all, nor is it a problem that needs to be rectified.

Stepping into this phase of self-realisation is a story for another time, but it was based on two specific moments: one, where my sexuality and sexual preferences were becoming clearer; and two, some honest friends shared some truths, as brutal as they were. Being able to see that I approach any form of relationship with reservation allowed me to understand that I like being in control of how much vulnerability I give over to other people (again, this is probably another point I should see a therapist about, but that is another story).

Though, why these are important factors is because late-twenties-me started to hit the ‘dating scene’ with a new drive of wanting to understand my sexuality without any expectation of commitment or longevity. In fact, the idea of meeting up with someone more than once was a weird thought and so I started to enjoy the apps for hook ups and random nights of fun. I had met a handful of people here and there, attended a few parties and always managed to maintain safe practices regardless of what situation I found myself in. I felt liberated in myself, understanding my quirks and desires as well as not limiting myself to new ideas or experiences.

But before we get into that conversation, it is important to share a bit more about my older sister. Throughout our lives, my sister and I have not been close. Not for any reason, it was just that our lives and passions are in different areas of the world. In saying this, I know that if it were ever needed, I would go to the end of the earth for her and I have no doubt that she would do the same for me. Recently, within the last year or so, my sister has entered the dating scene again. She is a fair number of years older than me, and so this is the first time where we have both been in the ‘dating scene’ together. Up until this time I had never really had to worry about my ‘adventurous tendencies’ because majority of my friends are coupled, and those that aren’t are looking for something completely different to the attention that I am seeking.

With entering the dating scene again, my sister had also found herself moving into her own place and creating a life to enjoy and thrive in. She had borrowed my car for a couple of days to help with moving her belongings, and so at the end of one moving day we found ourselves sitting on the balcony sharing a bottle of wine with some strawberries and cheese. We immersed ourselves in conversation, and naturally it turned to dating. My sister shared with me about a couple of people who she had been chatting with and told me about ‘Jay’, who seemed like a lovely guy and she had managed to meet up and go on a couple of dates with. He was a cop, had recently gone through the devastating reality of losing his wife to cancer. One of her major conversation points was that he was now a single dad, and that she was unsure how to navigate the space of respecting familial boundaries, as this was a new reality for her. To be able to sit and chat like this was not something that we had ever really done before. It was nice to hear about her life and what things that she was getting up to, though it was not something that either of us planned to seek regular updates about. I was happy that she had managed to find a space to enjoy her life and was pleased to know that she was not wallowing in her home, but rather aiming to create a space of entertainment.

A month or two went by and I was acutely cautious of ending up in the same chatroom with my sister. It was not an exceedingly high concern on my list, and I was sure I could recognise her profile and that my pseudonym and nondescript image would be enough of a disguise. Every now and again we had managed to catch up and she would share about a couple of other dates she had been on, and that she was living and enjoying her different lifestyle. I carried on my merry-sexual-exploration-way and continued to meet up with people, enjoy an adventurous evening, or six, and not cling on to any long-term thoughts. I was enjoying my status of ‘single’, and I lived into the experience of being ready to mingle. It wasn’t long before I started to chatting to a few new people over this time and started messaging a guy named ‘Jay’.

‘Jay’ and I spent a few weeks chatting about who we were and what brought two ‘single’ people to an app with no expectation of wanting a committed relationship. Over the numerous weeks of chatting ‘Jay’ and I shared in some good similarities of humour, and sexual expression, and shared our day-to-day adventures with one another. We got along incredibly well, and it didn’t seem like much of a surprise when the conversation turned toward ‘dating’. ‘Jay’ shared with me that he loved our conversations, and that he would have to think very carefully about his single lifestyle if he ever met someone he ‘clicked with’. On one hand I was quite undecided about the idea of being ‘that person’, but after being greeted with a ‘good morning’ and ‘sleep well’ text everyday for three weeks, I started to look at ‘Jay’ in a different light. He seemed sweet and friendly, worked as a cop and came to the dating scene because of the devastating reality of losing his late wife to cancer. Horrible.

Along with being someone who seemed genuine and honest, his high level of exploration and excitement for miscellaneous fun kept me intrigued. We had many discussions about meeting up, and living into some fantasies, which included other people and scenarios. I was all for exploring some fantasies with other people and continuing to unravel my sexuality more. ‘Jay’ mentioned that he had a friend, ‘Alice’, who he had met up with a couple of times in the past, and she would be keen to help me experience some new sexual fantasies. And so, myself, ‘Jay’ and ‘Alice’ set plans to meet up for a night together where we could explore more of one another, if you get what I mean. Because of ‘Jay’s’ work commitments, with being a cop and all, we could only settle on a date in three weeks’ time. This was not something that really bothered me, as it was just a night of fun, but ‘Jay’ continued to message every day with conversation and laughter, really sharing more of himself and wanting to know more of me. I would be lying if I did not think that maybe I could be the exception to his ‘no commitment’ rule.

While waiting out the three weeks before our scheduled rendezvous, my family had a few birthday celebrations, and there was a moment where I was privy to a conversation between my sister and our mother. They were chatting about the couple of guys that my sister was messaging, and our mum asked how ‘that ‘Jay’ guy’ was going. My sister said that it was all good, but he was not going to be very communicative over the next couple of weeks as he was going undercover.

My ears pricked up, and I chimed in, ‘Oh, undercover? Is ‘Jay’ a cop?’ My sister nodded and kept on chatting with our mum.

Suddenly my mind hit rewind. I started funnelling through the conversations that I had had with my sister about the guys she was talking to and what she shared about them. I was brought back to the conversation that we had had on the balcony, with wine and cheese, as she spoke about ‘Jay’ a widowed cop now single parent. Surely it could not be the same ‘Jay’ that I was talking to? but then again how many widowed cops named ‘Jay’ on dating sites could there be?

So I messaged him.

I started with saying, ‘I think that you are also chatting with my sister?’ He replied straight away. So much for being undercover.

‘Jay’ queried my sisters name, the handle she went by on the site and responded in a way that implied they had not been in contact very often. ‘Jay’s’ nonchalant attitude set alarm bells off loud and clear. You see, my sister has a very unusual name. It is a beautiful name, and in her late-thirty-year-old-life she has only ever met one other person with her name, of the opposite assigned gender, which was went by a different spelling. There was absolutely no need for him to query anything further. Her name is already enough information. We continued to message back and forth and ‘Jay’s’ energy was focussed on clarifying to me they had only spoken a handful of times and that they had met up once for a date.

Now, this information had not contradicted anything that my sister had share with me from months ago, but what I could not get out of my mind was that these conversations of sexual exploration and fantasies surely where not something that was limited just to me? But maybe they were just mine and ‘Jay’s’ conversations, and ‘Jay’ was meeting my explorative nature rather than it being his own. All I knew was that I am going to need to speak with my sister before I could even plan on meeting up with ‘Jay’, let alone ‘Jay’ and ‘Alice’.

The next weekend there was a second family gathering, and I was not sure where I should have broached the topic of ‘Jay’. So right before we left the house to head to the restaurant, I mentioned to my sister that I think that we are speaking to the same guy. She seemed surprised but asked who and I mentioned ‘Jay’. Her face dropped, and she hurried out of the room with her phone. Both of us took separate vehicles with the family, and throughout the night she spent the whole-time texting others and excusing herself from the table to speak on her phone. Now, the family was aware of what had happened as my sister was quite exasperated by the whole thing. Our other siblings were making it clear that it was not good form to be on-and-off the phone, as we rarely get time together as a family, and so I looked over and asked my sister if she wanted to talk about it together. We went into the car park and chatted about what was happening, and it was not long before we started to compare text messages. Boy, did these messages look eerily similar and even worse were the texts from the past week.

You see, across the past week ‘Jay’ understood he was messaging two sisters, but he continued to share in laughter, stories and pictures with both me and my sister. In fact, there were cases where these texts were copy and paste. I started to realise that this was not just a casual message here and there with my sister, but rather they had been on numerous dates, holidays and adventures together. And this was when reality sunk in. These conversations of sexual exploration and fantasies where not just something limited to me. This was ‘Jay’s’ M.O., and his nature was one-hundred-percent explorative.

I was mortified. My big sister was now fully aware of the sexual experiences that I liked, and even worse is the idea that I had been discussing these activities with someone who had practiced them on my sister. What is even worse is that ‘Jay’ had kept up this façade, telling my sister that she was the only person he was seeking a committed with. Now I was angry. It is already embarrassing enough that my sister and I now share more in common than either of us would ever like to discuss, but a sneaky rendezvous with me is vastly different to a-near-year-romance that he clearly had no intention of committing to. And, oddly, ‘Jay’ kept on messaging both of us as if there was no issue.

Over the coming days my sister had reflected on the past year and started to see things that, in my opinion, were obvious red flags. Such as wearing a band-aid over his wedding ring, always taking adventures away, and avoiding meeting at his own home. This lifestyle that ‘Jay’ lived, of country getaways and periods of time where he was uncontactable, was allusive and shifty. It started to become clear that the most logical assumption is that ‘Jay’ was a mischievous and bored husband.

Could you believe that there was one more thing to add to this, already mortifying, story?

Before I washed my hands clean of this situation, or at least attempted to scour this memory from my mind, I thought it best that I contacted ‘Alice’. I shared the story with her, and she was shocked and appalled – I shared that I did not want to judge people’s life choices, but rather I wanted to let her know that hooking any permanency to ‘Jay’ might not be the best discussion based on these current events. ‘Alice’ reciprocated the concern and then asked, ‘Oh, did you or your sister ever find out what his real name is?’

‘Excuse me?’ I was shocked that there was possibly another layer in this. My sister ‘dated’ someone for nearly a year by a name that was never his own.

‘Alice’ replied, ‘Yeah, on here he goes by ‘Jay’, but I think he forgot he matched with me on another site where he goes by ‘Jacob’.’

I want to erase this story from my life.

Completely shook.