The Soft Core of the Earth – The Mating Game

I’ve written about dating apps before. I hate them, and I hate that I’m back on them. But these days, it’s the most common route to meeting women, so I stoop to it. I hate social media. I had Facebook and Myspace for a period of three months in late 2005 and early 2006, before the former went public (you still had to have a university email to access it, and I worked for one at the time). Dating apps are the worst type of social media, as it’s just shopping for love – or more commonly, lust. 

I’m not especially photogenic to begin with, but I also have curious hair and a somewhat menacing beard, so that puts me at a competitive disadvantage from the start. As my mom has pointed out, I might have more luck with a haircut and a fresh shave, but I stopped taking advice from my parents decades ago, even when it’s wise. So, I work with a shrunken pool of options. I cast my net wide, covering roughly 60 miles from my adopted hometown. I throw out corny, and sometimes funny, pitches to dozens upon dozens of women. Since getting back on a dating app about a month ago, it may be closer to 100 messages. Hell, maybe more. My hit rate is low – statistically insignificant. 

But if you throw enough out there, a few are bound to be curious. I engage with those who reply, but many of those eventually run their course. Sometimes it’s hard to get a conversation going, especially if there are seemingly few things in common or the “vibe” never comes into being. Some I wonder why I messaged in the first place and they just fade away. Some get to a good flow, though, eventually. But even then, those don’t always make it to the real world – i.e., actually meeting up. 

Recently, I had two first dates scheduled on back-to-back nights. The first messaged me the day of and said she needed to cancel. She wasn’t “feeling up to it.” I never heard back from her, but for whatever reason, she didn’t unmatch us yet, which is weird. Her profile continues to exist in my portal, and I look at it as some untouchable oddity. The next gal simply unmatched before the already established date. I’m glad she did so before I bothered to get ready and go meet her. Would’ve been nice to know why it went that route. You don’t get a lot of good feedback on these things. 

I had another woman message me, one I’d previously passed on, but whatever, I was game to see where it would go. It strangely got nudged into the land of ‘role play’ by her doing and I went along with it. She started sending me pictures (you can guess the type) before too long and I figured I might as well see it through. After only a few days of interactions through the app and then via text, and without having met up in person, she alluded to the possibility that she could fall in love with me. Weird. Really weird. That was the end of the line for that one…

Another gal I’ve gone out with twice, but there was a full two weeks in between because of our conflicting schedules and distance – she’s about 65 miles away, which will inevitably be a dealbreaker, I imagine. Who wants to drive that far roundtrip to see someone all the time? 

Anyway, both times we’ve hung out we’ve had a really good time. But the communication in between has been terrible. I put this mostly on her – it’s kind of like pulling teeth to get her to engage meaningfully and in an extended fashion via text. I get it to a degree – who wants to do that before you’re actually involved, but I don’t know how else you’re supposed to move in that direction if you’re not otherwise seeing one another more frequently. Maybe that’s the point; she’s not interested in seeing me more regularly. If so, let’s cut the cord now. 

However, we’re supposed to meet up this Monday. And this will be her last chance – if we just stay drifting in this liminal zone of occasionally hanging out and not moving towards something physical (let alone a relationship), then I need to get out. Cut my losses. Not even sure why I’m giving this one more chance. Maybe I’m closer to desperation than I’d like to admit. 

I’m scanning through those who I’ve match with as I write, the ones who I haven’t made it to a date with yet but still have some steady communication happening. None of them are looking like winners. Which makes me feel like a loser. 

I’ve tried to just go out and meet women IRL, and that’s been a failure so far. Turns out I lost whatever game I may have had in the past; I’m terrible with the cold approach. Make an introduction, and I can charm the pants off someone (that is, after all, my intent). But I don’t have a lot of capable wingmen these days; most are liabilities. So, instead I struggle through this process I’d thought I’d left behind for good, waiting to see if I can ever get off this merry-go-around – it’s making me sick. 

Marco Esquandoles
Stuck in the Dating Loop