Glimpses (Part II)

“Why do you think you’re still single?”

Then I met the girl that I thought would end it all. Okay, that’s too strong, but at the very least, she stood out. I immediately extended our connection on the app because something in me clicked. Maybe it was intuition, or maybe it was the fact that she had the best dating profile I’d ever seen (I told her as much), but I wanted to meet her in person. Frankly, I’m better in person. I believe in my ability to hold a conversation. I also never know how to begin via text, so if we continue to talk, that feels like a victory. She checked off almost all of the boxes I thought I had. I tried to be calm, and to be myself as much as possible. She seemed to have embraced life in a way that was inspiring. Between having an interesting job and fascinating hobbies, she also possessed an emotional intelligence that caught me off guard. She was put together, and fully-formed as a person.

Part of me thought that, okay, this person is too cool for me, and she’s going to realize it. She’s living a life that she’s proud of, she’s challenging herself, what chance do I really have? I know I’ve worked hard on myself. I’m excited about the person I’ve become, and that I continue to become, but she is living life with vigor. I’m not sure I’ve gotten there yet. The night of our date, she came up to the bench I was sitting on, and said my name in a way that was intriguing. I would like to think I was cool and relaxed when we met. After all, if everything went south, I would still be at my favorite bar, and I would go back to the life I’m living now, which is as good as its ever been. Even so, there’s a part of me that’s ready to stop dating. It has a shelf life, and as wonderful as it is to meet new people, you run out of energy if you do it too much. I tell people my story, my family history, only to have to tell it again to someone new. I wanted to be fresh for this date, open to the experience, but I was also burning out. If this fizzled, I was overdue for some time off.

We chatted about a lot of things, and then the above question was asked. I wanted to be honest, even if I might incriminate myself in the process. I’m learning to be more honest, even if it might cause problems. In some ways, it’s been helpful. I am worried less about the outcomes, and as a result, I’m able to have more challenging conversations. I want to be genuine with people, and something about how open and genuine she was encouraged me. I dug deep, and talked about my last relationship. I was honest with my answers, said something to the effect that I hadn’t been entirely truthful in an effort to preserve the relationship, to maintain the bubble. I had wanted to make up for lost time, and put too much pressure on the situation. I’m sure I also said something about needing to work on myself, which is true, but not as potentially damaging to me, and this person’s image of me, which is still being formed. I decided to go big.

I gave the honest answer, and she appeared receptive. Somewhere during that conversation, I got self-conscious, and even though what I was saying was true, I felt like it might just be too much. Maybe my words were tinged with desperation, or maybe I am losing track at this point, track of how any of this is supposed to go. She seemed fine with my answer and our conversation, but we parted company without the promise of a second date. A subsequent text let me know that she hadn’t felt the connection, and she was going to trust herself on this one. I can’t say that I was surprised.

I appreciated the honesty, even as the text broke me. I had told my friends that I didn’t feel there would be a second date, and my suspicion was confirmed. I also told them that I was exhausted. It wasn’t her, it was the accumulation of just so many first dates. When you keep stalling out so early on, it’s hard not to feel stuck. Maybe you even question the point of dating, especially when it never seems to go anywhere. I was a beaten man, and in my defeat, I deleted my dating apps and finally took a much needed break. Sleep helped me to reset. I woke up feeling refreshed, and ready to go forward. I was ready to move on from the previous night’s events, although with regards to my dating life, I didn’t have a plan. I was oddly at peace with that.

I don’t know why I’ve been single this long, or maybe I do. I know that dating has never been a major priority. A friend once asked me about my priorities for the year, and conspicuously absent was the mention of women, or even finding a partner. For a long time, I wasn’t comfortable with myself around romantic prospects. I was hesitant, and would look for any out that I could find. I have a feeling that this happened on a subconscious level too. I couldn’t get myself to relax, and where others saw opportunity, I experienced tremendous anxiety. My first real relationship was such a mess at the end that it colored the way I saw that part of my life, and how I viewed myself in the relationship context. It’s been hard to shake that filter. I’m also more comfortable being myself, being alone. The end of each relationship arrives when I am called to return back to myself, to be a more genuine version of me. It’s like I’ve been asleep for months, and someone is shaking me to wake up. I can’t fight that feeling, and that’s kind of terrifying. That loving feeling can knock you over, and it can also leave you, just like that.

That brings me to a big question:

Would I even know her if she walked through the door?

Honestly, I’m not sure. I have some ideas, some theories, and that’s about it. I know that I value intelligence, and also warmth. I know that I want someone relaxed, without drama, and yet the two relationships where I was the most engaged were also the most drama-laden. I’m not sure what to make of that. More than anything, I want someone who is their own person, who has their own interests, and their own friends. I want someone who is as much a part of our relationship as they are an individual. I want someone with a true zest for living. It’s something that I once lacked, and to some degree I was even afraid of life. Now that there’s been a sea change, I want to enjoy this life as much as I can. I want someone that I can share all of myself with, even the parts that I’ve previously been ashamed of. I’m working every day to be more accepting of the parts that I’ve kept hidden, and I’m not as afraid to talk about them as I used to be.


I remember a conversation with a friend, where we talked about the check boxes we both had. My friend had met someone, and they’ve been together for some time. We both came to the realization that when you do meet that person, all the criteria that you thought you had, that it either falls away, or that you’re willing to make peace with the absence of certain things. When you have that connection, the things you thought you wanted or needed become far less important. If I’m ever to make it work, I need to find someone that I can be myself with, that I connect with, and maybe it’s time to let go of my preconceived notions about who that person will be. I also need to be with someone where I feel like I can be myself, where I don’t feel this urge to change myself, as I know how that ends. I’m admitting that I don’t know who it is that I want. I’ve met people that I thought would be perfect for me, only to realize that the connection just wasn’t there.

Every now and again, I get glimpses of what a potential partner could look like. It’s funny that I’m writing this particular post when I’m feeling so disillusioned with dating, when I have no idea what I’m doing. I’ve rarely been this lost when it comes to what I’m looking for. I’m confused, and yet, maybe this is the perfect time to write this post. Maybe it’s a time for taking stock, for analyzing the data, for meditating on my experiences, before I move on. I’m looking for someone that supports me in all of my endeavors, and I hope that I can offer them the same. More than anything, I want someone who’s just as out there as I am, and that is willing to explore the more interesting concepts of life. I am more than okay with being alone. I am happy to be alone, but I also wouldn’t mind a friend for the journey. Maybe I’ll know her when I see her, and she won’t just pass me by. Thanks for reading.


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