I have used dating apps off and on for a little over a decade. I never learned how to meet women the correct way – I always did so drunk at a bar and usually after midnight. This worked well until I didn’t like being drunk at bars or up after midnight. It was a bit of a challenge to course correct on this, and the only offramp I could find was dating apps. Being someone who despises social media in all forms, I found these platforms to be the worst of the worst – shopping for love (and/or lust). I also don’t present well in those forums, nor do I make the best pitches. I’ve never been great at the cold approach but give me an introduction (or a few shots of liquid courage) and I can win over even the toughest of audiences. Usually. But dating apps are different. It’s a fishing trip with no guarantee to eat. You have to cast your line hundreds of times to maybe get a few nibbles. Typically, I only get on these things for two weeks at a time – if I don’t get a date (or two), then I decouple (no pun intended) from them for a while (that’s all I can stomach). There’s something about them that just leaves a bad taste in my mouth; I don’t feel good about using them at all. But that’s how people meet these days, unfortunately, so I have no other choice (or so it seems).

This beautiful skyline screams hope and possibility. (Image retrieved from here and comes courtesy of James Wheeler.)

There are several apps out there I’ve used, Bumble, Hinge, and Feeld being the most common recently. Though, with Bumble, the woman has to make the first move, so you don’t get a fully fair shot in playing your best hand. Feeld is where all the sexual deviants go – fine by me – but that app only gives you a couple of free matches. I’m sure as hell not paying to use these things. So, Hinge has become my primary, as it basically has a frictionless function and you can reach out to whomever you’d like. Whether they respond is a different story.

In tandem with all the non-responses, I find this app also makes me feel a little bad about myself, but not in a “Boo-hoo-hoo, woe is me” kind of way, but that the women who reach out to me make me think I must be a lot uglier than I think I am. I’ll leave it at that; read into it what you will. But I’ve had some success over the years, and by that, I mean women I’ve gone on to date intentionally and with hopes of something that endured. The thing is, there is often some dissonance between what I envision in my mind and the reality of things. I often have to adjust my expectations (even if not consciously), and what comes to be understood as a “normal” relationship shows its true colors only after it’s over. For example, one gal, Kelsey, we dated for about 2-3 months three separate times each over the span of a year. We got along with one another, but there was some friction there, too, and we weren’t in perfect alignment on some (probably) key issues, and that caused us to have an extended feeling-one-another-out phase that ultimately ended in, well, the end of the relationship. At the time, though, I was trying to get myself to believe this was a functional relationship and I should adjust accordingly. That should have been the first red flag…

A quick aside: I went out with a male friend for lunch a few months ago, and I pointed to a man in his late 70s eating lunch by himself. I turned to my friend and said, “I don’t want to end up like him.” He told me I needed to do something about that now then. Do I have unreasonable expectations? Probably. Do I need to make more concessions, be more forgiving, and more open to that which I’ve previously dismissed? Probably. Easier said than done.

My typical approach on dating apps is to swipe left (not interested) in all women who have kids (or want them). It’s not that I have anything against children per se, I just don’t need that extra _____ in my life. A few years ago, a colleague of mine told me I was missing out on a lot of great opportunities, as there are plenty of very attractive, very cool women with kids. I’ve made some exceptions here and there, but mostly I’ve steered clear. That’s been the case for a couple years now.

On my most recent encounter with Hinge, I was at the end of my self-imposed 2-week engagement period, and about to delete the app. Hinge allows you to refresh so you can look at previous profiles you’d passed on, and I figured, “What the hell, why not?” I decided I would eliminate my criteria of passing on women with kids. The first one to pop up after the refresh was a woman with a young daughter (though, she didn’t share much info aside from that – which is a good thing, as women who yap too much about their children, and especially those who include pictures of them, are definitely out of consideration). I noticed a few things interesting about her and worthy of a cute comment, and so I fired off a message and then put the phone down. That was enough for that moment; I was just sick of the app. Then she replied to my message shortly thereafter…

We had an extended, but incremental, exchange through the app for two days, then she gave me her number where we transferred the conversation. We met up a few days later for our first date, one that lasted well over four hours and never saw a break in the discussion. We covered every topic conceivable and even got into the taboo ones as well, a sure sign of a good outing. We departed, eager to see one another again soon. Since that time, we’ve spent an awful lot of time together and communicated in every form you could imagine (text, email, phone calls, letters, playlists). The title of this essay came from the second date, as I was lying next to her on her bed, chatting. I said something along the lines of, “You know how the start of every relationship has that glimmer of hope and possibility?” She responded, “Yes,” smiling. I said, “Let’s hold onto that for as long as we can.” She replied, “I would like that.” We’ve been trying to do so ever since.

Marco Esquandoles
Cautiously Optimistic