dating

A TALE OF MILWAUKEE

I took a two-day trip to Milwaukee for two reasons: to get away from West Michigan and experience someplace else for a short while, and to meet a girl. I did both. And while writing this Weekly Post-Ed and describing my experiences, I felt that what I wrote wasn’t quite as true as the journals I kept during my time there. I was writing in a way that portrayed Milwaukee as mundane or uninteresting, which was far from the truth. There were mundane aspects about the trip: the drive was fine, the hotel was fine, the girl was – to put it nicely – fine. So, what gives? I traveled to some place I’ve never seen before, enamored with its architecture and history, a culture that was bustling and interwoven between every race, class, shape, and construct, like a fine soup streaming through the busy sidewalks of the city.

            And yet, I was writing about these experiences with a certain expectation after the fact;

            I was hoping for something cathartic to happen to me while I was there.

            Maybe I was supposed to run into an interesting group of people who would invite me to a party and offset how I saw the world up until that point, or that I might bump into someone in a coffee shop that was intrigued by me. No such things happened, of course, and I’ve sat at my computer for the past few days pondering what exactly to make of my time in Milwaukee.

            But maybe this isn’t such a complicated problem. I journaled all of my experiences on the road. The problem is that the length of these writings, even cut and pasted together, is a bit long for a Weekly Post-Ed. So, I’m going to compile these entries into a travelogue about what happened in Milwaukee.

            If you can’t wait for the juicy details, here’s a rundown of what happened:

1. Drove for 4.5 hours straight until arriving in Milwaukee.
2. Checked into the Drury Plaza Hotel
3. Walked the streets downtown, saw the river, saw Lake Michigan from the other side (looked similar, really).
4. Had a date that evening with someone I’ve talked with sparsely from a dating app.
5. Went to bed.
6. Spent most of the following day in my hotel, exhausted from a variety of factors (the lingering fatigue of my previous bout with Covid as one of them).
7. Walked the streets of Milwaukee on a Monday—fun fact, most everything is closed on Mondays in Milwaukee
8. Had a second date with the same girl; regretted not kissing her when I should have.
9. Slept early.
10.  Had brunch with this same date. No kiss, again. Regretted it, again.
11.  Drove 4.5 hours home.

            And somewhere in there was supposed to be this grand, ubiquitous breakthrough that would provide the foundation for a summer I’ve deemed as a fresh start, a way of cleansing the old for the new.

            What I found was that all of this did unfold on the trip, just not in the way I expected.

            In fact, I wrote it during my time in the hotel:

“I wouldn’t call it boredom, but there is a feeling of, “Is this all?” And, yes, I think that’s right. This is likely all, and the fun travelers have is the fun they make for themselves.”

            The Milwaukee 2022 Travelogue will be posted this weekend. Keep an eye out for that!

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PHOTOBOMBING

            There was a social experiment done at the University of Florida with a photography class. The class was split into two groups: the first group was told they were to be graded on QUANTITY—meaning, they were to take as many photos as possible for the best grade. The second group was told their grade would be based on QUALITY—or deciding upon a select group of photos that best exhibited their skills.

            The results of the experiment showed two things: first, that the QUANTITY group not only produced more photos, but that the quality of their photos was better. This was because the pressure to produce a select number of photos to be excellent didn’t exist. The QUANTITY group could take as many photos as they liked and the freedom to experiment led to considerably better results.

            The QUALITY group, by contrast, produced a significantly smaller number of photographs. Since the grade was about excellence, the students in this group did not take excess photos that would, as a result, push the boundaries of what they knew currently about photography. In short, the QUALITY group played it safe in order to appease the professor, which led to a stunting of growth with their photography skills and the photographs suffered as a result.

            The lesson that has been derived from this social experiment is that with more QUANTITY, it follows there will also be more QUALITY.

            Now, I wrote all of that to say that my experiences with dating apps DOES NOT FOLLOW these findings whatsoever.

            I’ve been online dating for 13 months (on and off, of course). Over that period, I’ve been on dates with 22 different women. Before this era of dating, I went on a grand total of 3 dates as a teenager and into my early college years, two of these dates developed into serious, long-term relationships (one a brief marriage), and I thought I was doing fairly well in terms of finding romantic partners that connected and resonated with me.

            By contrast, the past year has introduced me to dates with such staggering backgrounds and belief systems that I’m often left speechless by stories that I could never fathom to make up as a writer (believe me, I have tried—these stories are much more complex and surprising).

            My ultimate goal with dating is to find a meaningful, long-term relationship. And after 13 months, I have to ask: what’s been going wrong over the past year? Why haven’t I found a serious connection?

            In short: I don’t know.

            And after reading books, articles, and constantly introspecting on the matter…I don’t think anyone does.

            It appears we’re living in an era where genuine connection is a trial in and of itself.

            But I’ve certainly had a QUANTITY of dates (22 women in just over 52 weeks is a potent sample size in the greater dating world). So why hasn’t this led to better QUALITY in dates?

            First, I think bad luck plays a bigger role in the dating world than it does with a skill that can be improved over time like, say, photography. Dating certainly depends on many elements not in your control: natural chemistry, a person’s background/belief system/social ability, which leads to how open and communicative they are as dates, as well as a willingness to keep curious and want to know more about another person. This listing doesn’t account for other social conventions such as access to to instant gratification that has become available – oh, I don’t know – EVERYWHERE in the modern age (streaming services, social media, the internet and the never-ending wealth of information available instantly and from wherever to name a few).

            Since all of these variables are ever-shifting, it makes the practice of dating something impossible to master since you aren’t playing with a full deck of cards most nights.

            To take the photography example from above a bit further: it’s the equivalent of snapping a photo, but the resulting image is either distorted or that objects shifted in the background without warning. Can you imagine? A tree branch moves in the way of a crimson sunset, a sandhill appears blurry – not because of the camera settings, but just – you know – because it can. 

            Essentially, everything in the image can “PhotoBomb”—the act of jumping in front, garnering attention, or taking away from the intended intention of the photo by some means.

            That about wraps up what online dating feels like—a giant Photobomb that gets in the way of a genuine connection. Oh, things might have gone well except for (and I’ve experienced all of these and more):

• “I have a close relationship with my ex, I hope it’s not weird that I sometimes go to his house to spend the night when I need to get things off my chest. He’s such a great listener…”
• “I’m sorry, but I’m looking for someone that is seeking a relationship with Jesus like I am. It doesn’t seem like you go to church three nights a week like I do…”
• “I don’t trust men. I’ve had a string of bad relationships, the last guy cheated on me with three different girls, and I just don’t see the good in them anymore. Anyway, I’m glad we’re on this date; how was your day?”
• And on and on and on it goes…

            How does it feel to be on the dating scene for just over a year without the ultimate goal of a serious relationship?

            Picture that scene from the original Jumanji when Robin William’s character emerges from the board game and looks like a wild man who has survived the wilderness of a jungle that should have killed him since he was a kid.

            Yeah, that’s the psyche of someone who has online dated for too long.

            That’s why I take breaks. If not for my own sanity, but to remind myself that the results do not necessarily reflect the person. Will more practice lead to better results? Not really, but I like to think I gain something else with the more dates I go on.

            I have Twenty-Two unique stories to tell, each one of them more unique than the last. Each felt promising but was inevitably photobombed by something unexpected. If you think about it, 22 dates without coming close to a functional fit is quite the streak to be on.

            I should put together a photo album someday of all these experiences. Then, after this journey is said and done, I’ll pull out the album show a friend who wonders why I would ever keep such old, ugly things.

            “Why would you keep any of this?” she would ask as I flipped the plastic pages to the next story.

            And I’d shrug.

            Because I didn’t know what else to do with them.

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“Wonderful Life” by Two Door Cinema Club

“Ramona” by Jukebox the Ghost

“Out of Style” by The Wrecks

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Wishing everyone as well as you can be. You’re not alone out there,