I Went on 57 First Dates Last Year

57 is a big number when it comes to first dates in a single year, but to really understand the magnitude of it, I need to drive home the point that these are all real people, who like you or me, are the main characters in their lives. To that end, here’s a list of names:

Leah, Keese, Ani, Natalie, Jalissa, Anna, Nathaly, Yessie, Elizabeth, Valerie, Alexis, Mariam, Shy, Mel, Stacy, Sanny, Vèvè, Christine (x2), Gaby (x2), Nadia, Cher, Luba, Aliya, Sasha, Nya, Laura, Fulya, Kris, Neda, Nina, Schama, Meecah, Deedee, Phara, Olga, Hayley, Cindy, Imani, Paola, Bianca, Rami, Zoe, Yasmin, Si, Geniya, Stecie, Ashley, Kim, Carine, Isha, Amanda, Claudia, Maryinet, Maria, Sara

Some of them grew up around the same area as me, S. Florida, and we had been crossing each other’s paths over and over again for the last 30 years without knowing we’d one day be sharing an evening together. Others immigrated here from the opposite side of the world, and we happened to make a connection that otherwise would’ve never been possible. Some were older than me, some younger. There were professors, personal trainers, retail managers, entrepreneurs, doctors, architects, accountants, etc. Like me, they were all looking for love and struggling to find it.

I’ve repeated the process so many times that it’s almost automated: I do my swiping like anyone else. First, I check if I find them physically attractive or not, then, I look to read their prompts, occupation, etc., and decide whether or not I think we’d get along. Once we match, I scan their profile for something I can comment on to start a conversation. Usually there isn’t anything, so I go with two messages, “Hey!” and “How’s your day been?” Or, if it’s the weekend, “Hey!” and “Do anything fun this weekend?”

If they respond, which many don’t, I make conversation based on the information they give me. If the response is too dry for me to follow up on, they still typically ask, “And you?” I respond with a detailed description of my day and leave it up to them to make conversation or not from there. As the conversation progresses, I ask myself “will this be easy for them to respond to” before any message I send, and fit in questions as much as possible while still seeming natural. I understand that they’re probably messaging with at least 5 other guys between my messages, so I aim to make messaging me the path of least resistance.

After about five or six times of us both responding to each other, I try to transition to us going on a date. If the conversation is flowing, then as soon as we hit a meaty question, I say, “It’d probably be better to get into that in person.” I never directly ask women out any more. I say, “Are you free Saturday or Sunday evening?” Always two options for days, and always “are you free” instead of “do you want to meet.” Once they say, “yes,” or suggest another day, I say, “What’s your number? We can work out a time and place over text.” When arranging the date it’s always the same question: “What city are you coming from so that I can find something halfway?”

Most women expect for you to pay on the first date, and sometimes I’ve had five dates in a week, so I usually go for something like coffee or a walk in a park or by the beach. I did, however, go through a phase where I would go for drinks; I would usually pick the same spot every time. Eventually the bartender asked me when a date was in the bathroom if that place was my “date spot,” since she’d seen me in there with so many different women. That was awkward. If it’s anything indoors, I bring a jacket I don’t plan on wearing just to offer it to them if they get cold.

I usually run over the same lines: “Honestly, I’m bad at being a man: I don’t watch sports, know nothing about cars, and wouldn’t go hunting if you paid me to.” “Spanish was actually my first language, but I forgot it when I was a kid. Don’t often meet people who have forgotten a whole language so it’s something of a dubious distinction.” I tell the story of how I grew up with two brothers but now have three sisters. (TLDR: One of them is trans, my stepbrother became my ex-stepbrother after a divorce, and my two other sisters are so much younger or older that we didn’t really “grow up together.”) It’s all little fun facts about me or my life that are genuinely things I would say, but I also know at this point that people find them entertaining and that they lead to more conversation, so I repeat them every time.

I do intentional things to make them comfortable and spur on flirtation. I put a hand on their upper back as we pass through door ways or tell them to feel how cold my hands get if we’re inside a cold place. (My hands do get really cold for some reason.) I purposely speak low at points in the conversation to have them lean in towards me, and slow down the tempo of the conversation to create an air of intimacy. 57 dates later and every single one of them wanted a second date. The system is foolproof. But if that’s the case, why the hell aren’t I living with a woman I’m in love with right now?

Well, you probably got creeped out a little bit reading the description above, as did I writing it. It’s so mechanical, almost even sounds sociopathic and manipulative, but how could it not be? I’ve done this so many times, and it’s always the same. You’d fall into a routine for anything you do that often. I could describe my routine for what I do to get ready for bed at night in a similarly dispassionate and detailed way.

I’ve done this so much at this point that I wrote out what amounts to a checklist for compatibility. I fleshed it out in another article, but here are the five factors I consider: 1) general chemistry, 2) sexual chemistry, 3) shared interests, 4) shared values, and 5) the capacity to build together. I can now streamline the process with robotic efficiency.

Within 5 minutes of meeting a person, I can tell whether or not we have chemistry, and thereby whether or not there’s going to be a second date. About half of the time, there isn’t. That’s 57 down to ~28 basically at a glance. Also at a glance, there are all those people who took deceptive pictures, or used old ones, so maybe there are a handful more who I would’ve had chemistry with but don’t actually find attractive in real life. Let’s say the number is now 23.

Once we get deeper into things, the second or third date, I start to find out that the shared interests and shared values aren’t there. Let’s lob off another ten or so to 13. If we do have these things in common, then it’s time to take the relationship to the next level and see if we have any spark in the bedroom. I don’t know if this is the experience for most men; from what I’ve heard, it might not be. But, more often than not, I tend to be disappointed when I take a woman to bed, and if that’s the case, it becomes hard to imagine us being together in any serious way.

All in all, there were four women I saw any real potential for having something serious with after a few dates, and even with those, one I knew it ultimately wouldn’t work out with because she had two young children, and another I knew wasn’t really a fit, but I was drawn to her nonetheless and tried to make it work for a little while. That takes it from 57 down to two. I talked to them both for a while, but one was completely closed off emotionally, and things just kind of petered out as, after months, the relationship never progressed. The other handled conflict in an aggressive way, and whenever we started getting closer, a fight would pull us apart.

I don’t want to make myself seem blameless. Of course, if there are problems in any relationship between me and another person, I’m sure I’m contributing to it. Plus, I only have my perspective to offer you. But in all of these examples, I’m the one that ended things. I have a theory as to why these relationships are ending up a bit lopsided like that, but it’ll have to be the subject for another article.

As I lay out this story of my dating life in 2023, I ask myself the question, Am I good at dating? I know there are a lot of guys out there struggling to get dates, so 57 dates later, I’d think, yes, but if I can’t find love, then what is it all for? And that’s the issue with modern dating. We’re good at dating, but we suck at finding love. The process is efficient but soulless. Hell, I have a list of names in my phone a mile long! I have so many phone numbers now I could go into competition with the yellow pages, but I still don’t have a partner I can call if I get into a jam.

It got to the point last year where I fell into a brief depression from having to keep ending things with different women, one after another. It’s become like factory farming. It’s part of the continuum of how technology is affecting society as a whole. Everything is streamlined now, so comfortable and efficient, but we’ve zapped all the humanity out of it. We have 1,000 friends on social media, but we’re lonely in real life. We’re constantly entertained, but it’s by content that is vapid and insubstantial. We have all the information in the world at our fingertips, so we’re rarely ever called upon to think for ourselves.

I don’t like that modern dating has made me into something I’m not. I’m not built for treating love like a frivolity. I’m definitely not built for treating intimate encounters like something to be done by rote. And I hate that I feel the need to string some women along just to have something ongoing because I can’t seem to form the real connections I want.

I’m tired of putting on a performance and acting my way through the motions. I’m tired of holding someone in my arms just to have them go back to being a stranger a month later. I’m tired of seeing love in someone’s eyes and knowing that it’d be impossible for me to reciprocate it. I’m tired of getting my hopes up each time just to reach that inevitable moment when I realize that this too is not my person.