It wasn’t an easy decision last year to open myself up to the possibility of dating. It was something that I hadn’t needed to consider since I turned 21, and at 35, I found myself in unfamiliar territory. Considered the decline in my marriage, I had vaguely thought of my possible future always with a sense of a false bravado that I would endure and move on. However, the reality was far from this, as the thought of losing my family was soul destroy. It’s why, despite the loneliness I felt and the distance that had grown between us, my wife’s request for me to move out part-time, the death rattle of sorts, left me in tears for weeks. The next few months of uncertainty, loneliness, loss, and a feeling of inevitable left me at my lowest point. The tears had run dry, but it seemed at times my will was gone with them. When the end came, it was something of a mercy, although I doubt that made it easier for anyone. At least not for me as I continued to struggle lost in depression and uncertainty. I’m not sure what it was, but at some point, there was a spark, something that made me take control.

Complications and considerations

Perhaps having the will to do something may have been the most important step, but the considerations of dating as trans woman meant I needed to think about things more carefully. I know the stats on gender-based violence and the alarming situation for many trans people and I had read enough horror stories of rejection and humiliation that I knew I needed to be careful. Added to this, I had no clear idea of the type of relationship I wanted, and it was hard to work out a place to start. As a bisexual trans woman one main experience of being in a relationship I was lost on multiple fronts, who I was looking for, whether I was open to something series and even the possibility of exploring the poly lifestyle for a little while. These were questions that I realised eventually I was never going to be able to answer, I just might have to see what ended up feeling right.

The how, was perhaps a bit easier as online was the best option, so I fell back on some familiar habits and started researching dating apps, and after a little while, I found Taimi. It isn’t perfect and has issues as a dating platform, but I felt that using something with a LGBTQIA focus was immediately going to help me cut through some of the potential threats lurking out there. Making do with the free subscription was fine for me as I wanted to take it slow and being able to hide my profile, so I didn’t get bombard gave me a much-needed sense of control and ability to take things at my own pace. Once I started flicking through profiles, I very quickly started to develop some different criteria especially with guys as I felt a greater need for caution.

My dating check list

The first layer of vetting was and meant I passed on a lot of account but seems basic enough if you’re dating online. Simply it was people that didn’t really have much of a profile maybe just one sometimes out of focus photo and nothing really written about who they are. The fact these people hadn’t taken much effort suggested to me they weren’t serious, and the lack of information meant there was no way of knowing whether we had anything in common.

Age was the next step as I wasn’t against dating people either side of my own 35 years by roughly a 10-year margin. Firstly, out felt like going outside this range meant we would likely have less in common or at least not necessarily be able to relate to growing up in the 90s and early 00s in the same way. However, it also means we aren’t potentially at the same stage of life. People that are too young might be looking to party all the time or could be a bit more immature and are the age of some of my past students which is weird. While on the other hand after having a wife 6 years older than me I felt like an age difference much more than that would be a bit too much.

The next potential red flag for me was more specific to men and realistically is potentially a bit overly cautious and unfair to some. It was really avoiding guys that clearly identified as GYM junkies or hyper masculine, often they may have multiple muscle-bound photos flexing with some amazing bodies but really seemed to have little else in m profile. Now as someone keen on weights the idea of seeing some into lifting weights was not a bad thing but the image that many of these profiles present is that it was all they cared about. Now having grown up at an all-boys school I’d seen enough of the issues associated with hyper masculinity and the fact that most of these guys often identified as straight was concerning. One as their definition may not be trans inclusive or even if it was, they may be ashamed and potentially insecure about being in a relationship with me. It just didn’t feel right.

The next think was looking for common interests and realistically I was looking for a couple of things. One shared passion to me seemed insufficient but if there were multiple areas were we seemed to connect, especially if that was a good range of things they became a serious possibility. There were some things I valued more than others in part because they represent activities we could do together so it seemed like it was something that could work.

Finally, there were other little things that may have made profiles really capture my attention. An indication of their support or affirmation for trans identities was an obvious one which was a big reason for matching with my eventual boyfriend. Sexual orientation listed as bisexual or pansexual immediately put me at easy as I doubt there would be too many people in this category that were trans exclusive. Physical attraction came into my thoughts here but it wasn’t my top consideration but there needed to be something.

Probably the two things that didn’t really mean too much was gender and the type of relationship people were interested in. This was purely because I hadn’t really decided what I was looking for and was therefore open to anything. To me it was about putting myself out there and gaining some dating experience, perhaps meeting the right person while I was at it.

Chatting and getting to know people

This is hard for me. Despite the fact I am a teacher and public speaker I am not good at talking to people. I would say that in a lot of circumstances I can be socially awkward, quiet and very self-conscious to the point where I will often over analyse every possible faux pas and stupid comment. However, I figured that in this circumstance I really needed to try after all I was never going to meet anyone if I couldn’t get to know them a little.

So, here I was awkwardly starting a few chats with people. Normally I chose to use one of the commonalities in our interest after breaking the ice with the traditional ‘how are you going’. This had about a 50% success rate as there were a couple of good conversations where we obviously had a bit in common and realistically there may have been a couple where we were close to meeting up. However, there were others that were just painful, like pulling teeth where I felt like I was trying but getting vague level of disinterest in return. Of course, with these those social anxieties really started to eat away at me, did I say something, eventually after a few attempts with these people I’d inevitable give up. I expect that most of these people probably felt a similar way to me about interacting with others possibly even had far greater levels of anxiety but regardless of the reasons it just became too hard to persevere.

Organising a meeting

Besides creating a profile and getting started this was the most terrifying thing. It represents the most risk and all the added pressure of a first date. Considering this I didn’t want to rush so we had been talking for at least 3 to 4 weeks almost every day before we took the plunge, even then I did still feel a bit rushed. The fact I chose the location did help as I had the security of knowing the area and I knew familiarity would put me a little at ease. We also chose to start small with coffee which ultimately turned into a bit of a late lunch, but it meant there was no pressure to get dressed up to go out, there wasn’t going to be any alcohol, and it would be in broad day light. All considerations that helped take a bit of pressure off and made me feel a bit safer. The last consideration was making sure I had some sort of time limit or escape plan, in my case I had a commitment a little later, in hindsight this meant we couldn’t spend more time together when out date was going well. However, living it at a point where we both want to see each again and spend more time getting to know each other is perhaps the perfect set up for a second date.

One little thing to remember is that first dates are very rarely perfect. Maybe one of you is running late, spills a drink on themselves or says something awkward. It’s going to happen everyone in that situation is high strung. In my case, about 5 mins after I sat down, I realised that there was a current student sitting with her mum a few tables away. I was mortified. I spent at least the next 10 mins stressing about it and was somewhat distracted. Thankfully I relaxed but about half an hour later the student’s mum came over to show her appreciation for my work, I think I turned bright red. Of course, this meant her daughter had to follow up and come to apologies for her mother as well. At least it was positive. I think I spent the next two days or so wondering what the gossip would be around school but merciful nothing seemed to spread. Realistically, it was far from a disaster and is now something we can joke about.

Being a parent

Now, as a parent there was an ongoing consideration that influenced this whole process, my son. This gave me an added level of caution when looking over profiles as the possibility that things might get serious meant any perspective partner become part of his life as well. Considering this I chose not to include that I was a parent in my profile as I didn’t want to attract anyone that was potentially seeking me out because I had a son. It also meant that I could explore the possibility of a connection without it being something that needed to be discussed from the beginning. It would therefore give me time to think about how they might interact with my son and to gauge their genuine reaction when I mentioned him when we meet rather than the possible fake response I might get otherwise. Some might see this as dishonest but considering my willingness to disclose a lot on my profile I don’t have any qualms about this, especially since it worked out well.

Looking to the future

This whole dating experience ended up being much shorter lived then I had expected, so maybe something about my approach worked or I just got lucky. After only about 2 months a few dead-end conversations and a lot of freaking out I managed to meet a great guy, someone that is supportive, affirming and a lot of fun. It’s been 7 months now and things continue to be going well so I’d have to say that this little venture into the dating world has been worthwhile.