by Don Hall

Like the buds of flowers and weeds and nature slowly poking themselves up from the soil in the Spring of Chicago, so does my beaten and battered sense of romance. I wrote that "I believe... ...that once bitten, twice shy. Twice bitten, should be cautious but won’t be. Thrice bitten, the gift of both regret and fear are unwrapped. If you manage to be bitten four times, maybe you should just die already." I maintain this as a line in the sand for my personal path along the treacherous balance beam that is love.

As written, I can be grateful (sort of) to my third ex-wife for introducing me to both feelings of regret (something I've had very little of in my nearly six decades) and fear (also mostly absent). The last conversation I had with her as I was driving through the desert in the almost blinding dark of Utah at night I asked her if she had any regrets. Her response was that she regretted not successfully convincing me that being married to a sex worker was a good idea. She asked if I had any regrets and my answer was marrying her in the first place, which I did and do. As for fear, instilled in my bruised soul like a brand, is the lingering feeling that anyone I gift with my trust is going to shiv me in the ribs and take all my money. This sits on my brain like a malevolent lizard.

Saddled now with regret and fear, I am still a ridiculous optimist. While I no longer have any plans on marriage or even co-habitation, I am beginning to feel the desire to bring some of that feminine energy back into my life. As comfortable as I am riding solo it is apparent to me that a woman tends to make me a better person.

So, given my time constraints of rebooting my life in the big city, Hinge.

I've only done a dating app once before and that resulted in a four year, on and off, trek through insane sex and casual cruelty so I'm already on high alert. I decided to join for one month just to see. The app allows you to upload a profile with limited prompts, polls, audio and video. Six photos to brand yourself as 'dateable.' A persistent thought I've had about dating for decades is that we effectively lie to one another about ourselves to get a foot in the door, glossing over the things about us that are definitively not 'dateable' and, if we manage a few dates, are slowly discovered to have been less than forthcoming. The entire process feels like prepping for a job search.

I decide to throw up six photos that actually look like me without the goal of being enticing. I write prompts that are as honest I can be about what I'm like in the non-app world.

Whoa. I guess I'm not really looking to date at all, am I?

I limit my algorithmic search to women (cuz I'm straight), of any ethnicity (cuz who cares about that stuff?), 48 - 60 years old (let's try someone my own age for a change), within 25 miles of my location.

There are three ways to connect. You engage in the swipe, looking at other profiles, discarding the ones you aren't interested in (although they keep jumping back in unless you go through a few steps to let the app know you are definitely notinterested) and sending a like if you are. You can buy roses to send if you really like what you see.

There are a lot of ways for the app to get more money. You can boost your profile to be seen by more women for $30. The roses are $3 apiece with the guarantee that more women will date you if you send a digital flower. It's an entire ecosystem designed to prey on your insecurity and desperation.

After two weeks of strolling down the primrose (digital) path of busted and broken trust and hope I notice trends.

It seems that among the subset of women between 48 - 60 years old a majority of them do yoga, love tacos, want to travel more (or have traveled a lot), and play pickleball. Within that subset are a number looking for honest men as a specific trait (as if this weren’t apparent but still needed saying). A favorite consistency is the photo of a dour looking woman with the admonition right below “Make me laugh.” A bunch of them love to hike and ride bikes. A fair amount are either conservative or are very specific about not entertaining Trumpers.

Lotsa golfers. I’m no spring chicken but a host of women my age have not aged well. Plenty of what we’ll call ‘robust gals’ in play and I prefer ladies on the thinner and younger side. I don’t feel bad about my preference because apparently being someone who smokes is the number one dealbreaker for most of the Hinge broads (as are men who use the term ‘broads’). I can’t take seriously women so threatened by the fact that men tend to prefer younger women that they attempt to shame them. They’re simply aware that without the shame, they will eventually age out.

There is the possibility that I have aged out but I’m not angry about it. Hell, I wouldn't date me with my crackling resume and history of failure yet I’ve received seven digital roses so there must something there. I would say that my entire experiment with dating after a post-apocalyptic divorce at nearly sixty has resulted primarily in an overwhelming sense of bemusement.

Thoughts for the profiles I've seen in the past few weeks:

• If your college age daughter is hot, best not put up a picture of the two of you together. Dudes are visual and the newer model is the one they're looking at.

• Men with serious money aren't going on Hinge for dates so your clarification that you want to travel the world is like wishing into a Fritos bag.

• Don't use a filter on your photos. We can tell.

• Telling prospective dates that they need to be active because you're always 'on the go' is an empty challenge. Guys who hike, run, or are into serious fitness aren't on Hinge. They don't need to be.

• Pickleball? Really?

On a more serious note, I find a lot of the scrolling a bit sad. Everyone on this app is looking for someone to love them and, like me, have failed in their lives. In the age group I'm looking at, these failures have cost them and you can read between the lines and in the photos and audio messages the effects of those missteps.

The adamance of noting on a profile with a limited word count that the man you are seeking isn't married or currently in the midst of a divorce says a lot about those misadventures as the almost constant request for someone honest before all. Maybe pickleball is the new Spanish Fly and I just didn't get the memo?

The game as it is set forth is to connect and chat. 'Chat' is the euphemism for texting one another from within the app. I find this to be alienating so, when I do find a mutual interest, I pretty quickly send them my full name (to Google and be horrified) and my phone number to call if they are slightly less horrified.

In two weeks, only one out of five does not call me which indicates my Google results are not as bad as I think or the level of desperation is quite serious out there.

The shortest conversation was with a lovely 49-year old suburbanite. She called and immediately shared that she wasn’t strictly single but was separated and exploring. I politely demurred and told her to keep my number. If she was still interested after she was divorced, she could gimme a ring.

The longest went around ninety minutes. 52-years old. Pretty but not the dirty librarian model I usually gravitate to. A professor who does pottery and loves live theater. She called and we got into it. I found myself in my familiar pattern—she mentioned at least four times that our lifestyles were very different—so I doubled down to convince her that we should at least go out and see. She lives a relaxed, slow grind and I am on fire doing as much as I can. She did Google me and had questions about the book and the divorce so I told her.

After we hung up, I replayed the conversation in my head and realized she was being cautiously polite. She told me in her way that she was skeptical of any sort of thang but I was hellbent on doing that other thang I do—selling her on the idea of me despite her reservations. I called her back and told her my Achilles heel is women not interested in me at the outset and taking that on as a challenge. It rarely works out well so I let her off the hook. She was relieved and we agreed that if I ever was in the neighborhood of her pottery studio, I’d swing by and say hi.

If there is a discovery within this experiment it is that I'm just not ready for this right now. Not in a wounded bird sort of way but in a wholly apathetic mindset. "You're five blocks from my apartment? Hmmm. I'll pass. I'm looking for someone, like, two blocks away. Too much effort to go that extra three blocks, y'know?" I'm genuinely enjoying my quasi-misanthropic existence. I like living by myself at this point knowing fully the pitfalls of having a partner sharing the space. I'm almost mortified at the prospect of going on a date and making flirty smalltalk.

I'm not some version of Quiz Kid Donnie Smith bemoaning that I have love to give put don't know where to put it. I'm more like Melvin Udall, content to do my thing, my way, without too much unnecessary potholes to navigate who may meet someone but who is no hurry to do so.

As for Hinge, I'll let the subscription expire and go out into the world. Maybe I meet someone. Maybe I meet lots of someones. And maybe I'll be just fine alone.