Glimpses (Part I)

“Do you feel pressure?”

“No, well, maybe a little bit.”


“There’s pressure to see if we connect.”

I was asked the above question during a somewhat recent date. On the whole, the conversation flowed. In our conversations, we talked about little things like where we had lived, but the conversation also went deeper than I’m used to, or maybe I’m only now aware of it, this pattern. The above question was asked, and when I mull it over, I realize that I was downplaying the pressure that I felt. It wasn’t the pressure of getting older, that I needed to get moving. It wasn’t the pressure of wanting to start a family (on the whole, I don’t care one way or the other). It was the kind of pressure that bordered on frustration, frustration with the dating world. I know I’m ready for something more substantive, but it’s not my time just yet. I once thought that dating would get easier in my thirties. At least I can admit when I’m wrong.

This post started writing itself on my way home, as I cruised down the highway and into Boston, after a good day of work. I thought about dating, and how I may have it all wrong. As I sit here and write this, I can admit to my high level of frustration. There has been one relationship in my thirties, and way too many first dates that have gone absolutely nowhere. It’s the strangest thing, I told my stepmother, the wonderful woman that wants to set up her children with their person. I’ve had a lot of dates where we have a wonderful time, good conversation, fantastic food and drink, and then no one follows up, and we never speak again. Maybe I was supposed to reach out. I guess I feel that in this day and age, that either person can follow up, and I do like people that aren’t afraid to go for it. I love how much I can connect with people, but maybe it bothers me that I can’t tell when the connection might be romantic. I get along well with everyone, and I also tend to be oblivious.

As it stands, I’m on a dating hiatus until 2023. A friend let me know that she read an older piece of mine, and had deleted all of her dating apps. We hadn’t spoken in some time, but maybe her disclosure made me realize it was time for me to delete mine too. I still had my apps when we connected, but I was at a crossroads. Dating apps are not the greatest. They are wonderfully flawed, but I also know someone that met their partner through one of them, and they’ve been together for a while. I suppose that that was reason enough to stay with them, the apps, in hopes they would yield something promising. Maybe that was the reason, or maybe I’m just out of ideas. It’s happened before. I’d be on dating apps for a while, I’d take a break, and I’d return, mostly because I don’t know any other way to meet people besides apps or getting set up by friends/family. I finally deleted them, and I’d love to tell you that I’ll be back in less than two months. I’d love to tell you that, but I’m not sure that it’s true. I definitely won’t hold myself to it.

A friend shook up my world with his comments that I tend to be pretty at ease, free flowing in my life, or just in flow. Despite this mode of operating, he said that dating seemed to be the one aspect of my life that I was forcing, and he was right. The insight woke me up. I’m stuck in this model that is both unconventional and conventional. It’s unconventional because it still feels like dating apps are newish. It’s conventional because I’m still just playing the odds. Go on a bunch of dates and see if something sticks, with no guarantees, and no end in sight. There’s no promise that any of these dates will go anywhere. A former therapist of mine told me that you have to put skin in the game if you want to win. At the time, I think we were talking about applying for jobs, but it applies here. You have to meet people, put yourself out there if you want to find someone, and yet, you can only do that for so long before you lose your energy and enthusiasm. After a sustained period of putting myself out there, I find myself no longer having fun. Instead, I’m feeling pretty run down. The way to do life is to have fun with whatever you’re doing, and I need to be able to walk away from something when I’m not having a good time, or at least change my mindset.

I don’t know what’s next. I’m off until next year at the least. If and when I do come back, I don’t know in what form it’ll be. I’m saying goodbye to the apps for now because I just can’t do them anymore. There has to be another way, another way to casually meet people out in the wild. I wouldn’t say no to a date if asked, but I’m not looking right now. Instead, I’m focusing my time and energy on other pursuits, and I also want to enjoy this time around the holidays. I’ve never been good at this aspect of life. I’ve never had a great relationship. I’ve dated great people, but the connection has never been what I thought it would be, or even should be. I’ve never been able to get it all in one person. With each relationship, it’s always felt like something was missing. More work was needed, I assured myself, but if you wait until your perfect, you’re going to be waiting a long time.

And yet, there are moments. Every now and again, I get glimpses. I get glimpses of what it would be like if I found someone that I truly connected with. I go back to memories like laughing and having a blast in a grocery store, just having an adventure in a place that is mostly mundane, with a good friend of mine. I think about a day where I hung out with another friend, we bounced around to different locations, and just enjoyed spending the entire day together. I’m not focused on the romantic aspect of these encounters, partly because there is none. What I do focus on is the fact that the right person, the right connection, can make any experience infinitely more enjoyable. Maybe these moments mean nothing, but in my eyes, there’s something significant about the forced versus the organic nature of these moments. Maybe I am getting closer, or at least I’m getting a preview, the free trial.

Maybe it’s time to ask myself the hard questions, like do I really want this, or am I just mad I suck at something, and can’t make sense of it? I want to know why. I want to know why something doesn’t make sense or doesn’t work, and this is breaking my brain in a way that I can’t comprehend. I’ve spent my entire adult life trying to get a handle on dating, and maybe now it’s time to change my entire point of view. I’m open to suggestions. These visions may never last, but at least it feels like I am getting somewhere, maybe. In my best of moments, I would tell you that I know what I want in a partner. In my worst, I would tell you that I’m more lost than I’ve ever been. The glimpses give me hope. I know that I can’t stay in them, but they give me a quick look at the future that could be possible when I stop putting pressure on the situation, and start enjoying myself more. Thanks for reading.


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