Kendra stars in an awkward dating montage

Over the past couple of years, I’ve dabbled in online dating. Meeting people as a relatively introverted adult in a geographically enormous city with very limited night life can be challenging, to say the least. Online dating seemed like a safe option when I was re-emerging as a social adult from the insulated cocoon that was my life throughout my long-term relationship of ten years. I won’t say that online dating has been an entirely positive or negative experience, and I’m not sure, were I to repeat that experience, that I would start online again, but it’s been a learning experience thus far. In fact, it continues to be a learning experience each occasion I have to use it.

I didn’t date before I met my former long-term partner. She was the first person I met and connected easily with, the first person I felt comfortable exploring opportunities with, the first person I felt I could be myself with. In a way, I lucked out in finding a compatible partner as young as I did and being able to share a decade with her before we went our separate ways. However, in another way, I missed out on the necessary young adult experiences that teach people how to be with different people, how to explore who they are, how to fairly set and enforce boundaries, and how to develop the filters that are integral to finding partners in the future.

When she and I split, I was at a loss for how to re-integrate with adults. Being in a common-law relationship can make you complacent. It lulls you into repetition, into predictability, into comfort. You let the nuances of interaction with adults slide and lose the social graces that would potentially be essential to being with other people in a romantic or sexual sense. You can develop bad habits, like I did; her jealousy over the idea that I would want to be with a man led me to avoid interactions with men, even to the point of avoiding eye contact with them. It took me months to learn how to look men in the eye again, and that’s preposterous. Not only had I let social graces slide, I also lacked all the skills I could have developed in my 20s and was coming into my 30s with extremely limited experience. I felt like a teenager again, and when you’re finished university and looking to be a “real adult,” that’s a truly rotten feeling. On top of all that, I also emerged into the dating world in a completely alien environment! Dating wasn’t something people readily did online before my ex and I had gotten together in 2008. The proliferation of dating apps occurred while we were together, and their use was something I had literally no history with.

As you can imagine, my first few forays into dating were awkward and challenging. I met a number of really lovely people, and more people who were honestly questionable at best. I have been ghosted more times than I care to think about. I got into a couple of situations that were emotionally unhealthy and caused me a great deal of discomfort and unhappiness. I got into a couple of physical situations that were risky or uncomfortable. I was assaulted on a first date with someone. Realistically, these are always risks that you assume when you engage with others, romantically or not, but somehow the stakes seem a bit higher when the potential for romance is in the cards.

Naturally, dating can also give you cause for some self reflection and evaluation. I’ve driven myself crazy wondering what it is about me that this person didn’t like, or why that person was so eager online and then so cold in person. It’s easy to allow your self-esteem to get wrapped up in the opinions of people you’ve agreed to meet, and I am still on a very serious journey of accepting what and who I am. The what, more than the who, honestly. My biggest struggle, as most people who know me will attest, is my insecurity with my appearance. I spent much of my life mortified at my own existence and ashamed of the body I occupy. In the last couple of years, I have lost weight, gained muscle, lost muscle, and gained weight. The difficulties in coming to terms with bodily transformations will no doubt be a continual challenge for me, but entering into the dating world as an insecure adult was fucking hard. I’ve had a lot of good, positive reinforcement and assurance of my appeal to a variety of people, which is good. I am doing my best to remind myself that despite my own misgivings about how I look, I should allow myself to accept the interest, affection, and appreciation of others.

As I’ve done more exploration with others in the realm of romance, I’ve learned a lot. These lessons aren’t always easily or painlessly learned, but I am learning them nonetheless. I had something of a revelatory moment in discussion with my therapist, who is a marvelous man whom I have come to trust a great deal. I had shared some of my dating excitement and experiences with my sister, who has zero interest in dating or romance but who humours me nonetheless. I showed her a picture of someone I had plans to meet, and had said at the time that he wasn’t what I would normally go for. She said that might be good, because the people I would normally go for haven’t seemed to be good choices. I was pretty upset at the time, but I couldn’t put into words why. After chatting with my therapist about it, I realized I was upset because I was still learning how to improve my choices and build the filters I need to make sure that future endeavours are less risk-laden, less uncomfortable, and more likely to work out well. I can’t build those filters without experience, and there’s really only one way to accrue experience. To be judged on doing that learning stung some. I know she meant no harm, but it was important for me to pinpoint why the comment upset me and to avoid being left without explanation or rationale the next time something similar arose in conversation.

Learning to establish these filters for myself is simultaneously teaching me what I like and need in others and in myself. It’s helping me to identify areas in my own life that I can work on to become happier with, like being firm in my boundaries and walking away from situations I find compromising or unacceptable. I’m learning what I really can and cannot deal with in a partner, and what sort of accommodation I can make for the presence of another person close in my life. As you age, your certainty about elements of your personality and world becomes more fixed, and compromise on some essential points becomes a lot harder. I’m learning the difference what I’d really like to see in someone and what I need to see in them, and how to make that decision.

Life is about growth and transformation. I’m grateful to be able to learn more about myself, and to be surrounded by supportive, loving people while I do it. I’m sure there are many other awkward moments in my future, but they’ll teach me something no matter what.



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