Social Skills in Transition

Alicia Anderson
The Startup
Published in
8 min readJan 26, 2020

My life has improved immeasurably since I started my transition. I’m happier, more comfortable with myself and my surroundings, and more secure in who I am. I suppose it’s only natural that I’ve started handling social situations better than I ever did before. But, after living a non-social life for thirty years, living a more social life has been trickier than I expected.

My struggle with being more social has been a lifelong journey. I started as a nerdy, awkward child, but after a very tough year in a new city where I had trouble making friends, I resolved to be a more likable person. I found a few ways to improve and I eventually started to get along with people a bit better. I grew into a person that was outwardly more easy-going and relatable. It took me a lot of effort to seem “normal”, but I achieved that goal by the time I went to college. Many people I met never learned that I was still the quiet, nerdy person I always was, and that I had a lot more trouble in social situations than I was letting on.

I get the feeling that, when you’re growing up as a closeted trans kid, a lot of your interactions with others are fake to some degree because you’re unable to truly show yourself at all. When you combine that with the lack of social skill I had from my young childhood, I think that barrier would be difficult for a lot of people to overcome.

Moving forward to the present day, I feel like I barely resemble the person I was. I’m more free, I’m happier, and I’m able to share my genuine self with the world. I’m doing so much better in every aspect of my life. This seems like the perfect time to bookend the old story and move on to the next one. It would be a great end to my character arc to say that I’ve become a natural social butterfly. But, I’ve been learning the hard way that, even though I now have the desire and capacity to be a much more social person, my skills are still lacking. I’ve been putting in a lot more effort recently, putting myself in the sorts of social situations that I used to avoid. Unfortunately, it’s been a good reminder of why I avoided them in the first place. Socializing is still really difficult!

Learning how to socialize has been my goal for the last six months. I’ve put myself out there quite a lot recently, with a few decent successes and a few failures. Unfortunately, the failures still sting as much as they ever did, but I’ve already made some improvements, and I’ve identified places where I need to improve further.

Transition isn’t just about the physical changes. It’s also about taking action to carve out my own place in society, rather than accept the poorly-fitting role that I was given. My new self is more social than my old self was, and it’s been tough to step in to that new role, when I only have the insufficient techniques my old self developed. I’m determined to become the better person I always dreamed of being, though, so I plan to keep fighting until I figure this all out.

Back in high school, it took some serious effort to be perceived as a “normal” person, especially with the reputation I had already built. I was really just trying to go from “unlikable” to “likable”. As a part of this, I used an outward persona that was more easy-going as a contrast to my naturally serious personality, and talked about topics that others could relate to much more easily than my actual nerdy interests. This actually worked. I was finally able to change enough of my outward personality that I could finally hold some normal conversations with my peers. That made it a lot easier to invite people in to my world.

I figured out one of the major problems as I transitioned. I had always changed my persona to adapt to my surroundings and make myself fit in the best I could, but the transition was a drastic shift away from constantly hiding myself to living genuinely, so I had to start living without the false personality.

I realized that many of those interactions I had while trying to be relatable were shallow. I could keep up a conversation about a lot of topics, but when they started going in detail at all, the conversation lost me. I had put in so much effort to be better at small talk, despite never having enjoyed small talk, but I had a very hard time turning it into a deeper conversation unless it was on my terms.

I identified one technique in particular that was falling short of what I wanted. I would have a hard time participating in group conversations, even when I was definitely part of the group. I would often fail to get engaged in a conversation and it would go somewhere else without me, sometimes literally. So, I eventually learned how to inject myself in to these conversations by periodically mentioning how the topic relates to me. It was an improvement. I was finally a participant in the conversation.

But, even though I finally became a participant, I usually wouldn’t engage the others, and I wouldn’t end up driving the conversation. It wouldn’t take too long before it ended up in a topic I could no longer relate to at all.

So, I eventually learned that the old techniques were no longer effective enough to work on their own. I would have to learn some new skills if I was going to build better relationships.

As I spent more time socializing, observing the social skills of others, and failing a few times, I eventually figured out one of my bigger failings in conversation. It came as a eureka moment a few months ago.

I realized that in my interactions, I would very rarely ask others about themselves. I wouldn’t prompt them to talk more about things that interested them. I would never actually do anything to engage them in conversation, unless it was a topic that I was already interested in.

Why on earth had I never figured out how to keep others in a conversation by asking questions about them? It seems like such a simple but necessary part of a basic conversation. A conversation is a two-way street, and I had almost never met someone in the middle. Thinking of the many interactions I’ve had with people, I realized that people had put in a lot of effort to engage me, so they must have already known this. I was very, very late to the party.

With everything I’ve been through, I can see how I got this far without figuring that out. My social skills had always been weak, and in high school, I was just trying to get by, so I focused inward to improve.

But, once I gained those skills, I think that gender dysphoria was what kept me looking inward. My interactions with others had never really seemed right. I was never comfortable with who I was, so I kept trying to improve myself, but I never improved myself in the way that actually mattered, until I started my transition almost two years ago.

Once I started my transition, I was able to think more clearly in a lot of ways. Some of that was hormones, and some of it was finally having a sense of internal harmony for the first time. I think that was what I needed to finally get out of my own head a bit in my interactions with others.

Knowing what’s wrong is a huge step in the right direction. Changing it is a another issue, though. I have a much better idea of what I should do to improve, but, well, I’m new to it. Conversing in a way that engages others is a skill, and I’ve never really practiced it or learned how to integrate it into my other interactions.

I’ve been doing a little bit better. I’ve noticed that it’s getting slightly more natural for me to ask people more about something they’re talking about. I still have a long way to go, though.

I’ve also noticed much more often recently when others are either not interested in my conversation topic, or in a few cases, when they actually really dislike the topic. I’m so used to talking about recent events as a small talk topic, but when some of my recent events have been incredibly, extremely painful, I sometimes forget that many people aren’t as desensitized to it as I’ve become.

I recently re-joined an online game and community where I spent a lot of time in my college years, and this experience has also really highlighted some of my social shortcomings.

I probably should have expected people to not remember me when I came back. I was always at my best when I was helping others, so I naturally gravitated to those parts of the community focused on helping newer players. For a while, I was the most active person in that community, but I had always limited my interactions with others to talking about things within the game. And when I returned, I realized that I had never built a personal connection with anyone in the game. I was kinda sad that nobody remembered me, but then again, there wasn’t anyone in particular I was looking forward to seeing again either.

I’ve been trying to interact with people on a more personal level, but I keep gravitating to my old behavior. I’m still really good at answering questions and helping people, but I still suck at forging the personal connections that I’d like to have.

I’m still not entirely sure what I have to do to improve. I’ve identified the problem, but I don’t see an easy fix. This seems very connected to my other social issues, and I think that improving in one will help the others. I think I’m just going to have to experiment.

I have so much more to think about in conversations than I used to, and I already have a lot of new things to think about. It’s hard enough to simply take on a new societal role, but adding all of this to it makes it much harder. I’m determined to be a better person than I was, though, so I’m going to put in my best effort.

I’ve always had the desire to be better in social situations. Since the transition, now I have the ability. And now, I just need to develop the skill to turn that ability into reality.

In the spirit of trying to be better at socializing, I’d like to ask what you think. If you had struggles with social skills, were you able to overcome them, and if so, how? If you’re also trans, did you go through a similar change? Or were you always a skilled conversationalist? Do you have any advice for me, or can I help you with something that I’ve learned?

Two young girls talking while sitting on pavement.

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Alicia Anderson
The Startup

Data engineer, Magic: The Gathering Judge, trans woman, game connoisseur