What the Dick is Wrong with Men
And other Conclusions on Dating, the Patriarchy, Gender normative behaviors, and why Women are amazing (Part I)
What is Wrong With Me
Let’s start with a general lay of the land. Because to tell you what is wrong with men, you must know what is wrong with me, the one observing, sampling, and judging. I’m a heterosexual cis woman. A Gen Xer.
I’m a wild horse attracted to other wild horses, though sometimes I’m sensible and date British men who say funny things and make me laugh. I color outside the lines on principle. Yet, I’m a rule follower who cannot stand rule followers. My sunsign is Aries—the home of the blood planet Mars, the god of fire, the god of war. I’m naturally violent and aggressive. Fortunately, I’m small.
I say true things to people about what’s wrong with them, daily, openly, sometimes even at work, the moment it occurs to me, while also adoring people with the deepest flaws. I like to rip covers off flaws and point to them like rare species of moths. I dissect them. I pin them to boards. I like it when people tell me uncomfortable truths about themselves, about me, about their lives.
I join groups, but am always the freak. I go to run clubs and sometimes book clubs (though I rarely read the book because I have other books I’m busy with) and feel as comfortable in a bar in rural Alaska as I do in Manhattan. I have a dark sense of humor, and I’m tragically independent. I’m that woman you’ve seen on Instagram driving her own coffin to the grave.
I love men, yet have always been opposed to marriage and have never been more unhappy than when I was trapped in a marriage-like situation, complete with gender normative expectations for me. I’m someone who, if it were announced on the eleven o’clock news that I’d buried a man (or several) in the woods and burned down a neighborhood, no one would question my guilt. They’d question how I got caught and which man. I’d be popular in prison with the inmates and the guards.
Me after a hike with James to the top of Mt Batur in Bali to watch the sun rise.
Forty-Year-Old Men
I date men. This is a terrible pastime, and as many women have pointed out, if attraction were a choice, this is not one we’d make. Drinking margaritas and sitting in hot tubs, engaging in deep conversations with beautiful women, is what I’d do, is what anyone sensible would do, if given a choice. Instead, I’m stuck with men.
With all that said, there are other things to know.
I’ve been dating forty-year-old men since I was twenty-something. I’m now fifty-two. Hence, I have some experience with men.
Men who are forty have learned to endure women. They’ve learned to love women. They’ve learned what not to say and how to treat you. They are too old to be vapidly stupid and too young to be pathetic. They are in the sweet spot before their asses fall off along with the hair on their heads. I’ve had a few favorite men who were as young as thirty-six, but always, when they hit forty, they are a perfectly ripened avocado. They will never be better than this. Split them open and scoop them directly into your mouth.
If you meet a man who was not a specimen for show at forty, there is a good chance he never will be. When people speak of the power of the human spirit to evolve, those people are talking about women. We evolve till our deaths. We take up weight lifting at ninety. We are octogenarians still considering how we can reinvent ourselves—we become park rangers and hike the Appalachian Trail at seventy; we go back to college at sixty and become botanists; we write our first novels at fifty and take up fencing.
All this after careers and childbirth and endless laundry and ferrying children to sports.
Meanwhile, men get old, play golf, and wait for their dinner.
Karl
(Not his real name)
Last Saturday, I went on a date with a man we’ll call Karl. Karl was fifty-six, and though he was an over-ripe avocado, who am I to be ageist? I thought. I’m still angry that my 18+ co-ed soccer team pitched me to the curb when I turned fifty, so maybe I needed to rethink my dating preferences, I reasoned as I looked in the mirror at my neck sag.
I should sample the 50s field, I thought, because how long will forty-year-old men still want to date me?
Possibly forever, cuz amazing, I reminded myself
Karl checked enough compatibility blocks to make it to a third date. We’d met for dinner and drinks twice, talked on the phone several times at length about things like how best to get cash in Mexico and the places he’d gone spearfishing. He was tall and thin, well-groomed with a full head of dark hair and a master’s degree. He worked a government job outdoors doing scientific research. He was outdoorsy and conversed intelligently about his analysis and his life. He used words like mercurial and evapotranspiration; he talked both figuratively and metaphorically about flipping over rocks to see what you find. Often in the evening, he’d text me links to songs by John Hiatt, Greta Van Fleet, Gillian Welch, or the Cowboy Junkees—music that indicated a man with a soul.
Sidebar on ENM
If you’re someone who knows my boyfriend James, and you’re wondering what happened to James. Nothing. We always agreed to see other people, and do this thing called Ethical Non-Monogamy (ENM), and so we are dating other people and each other. Besides, James travels for work or to see his kids quite often leaving lots of gap time when I’d like to enjoy other people. But mostly, we’re both just having dinner with other people, and then I complain to James about what is wrong with men, and he tells me about yet another fascinating woman who probably spent decades reinventing herself to show up amazing and have dinner with James.
The Hiking/Dinner Date Options
I was in Austin the week before the third date with Karl, for a work conference on data. As a sidenote, I like taking numbers and turning them into visual representations of numbers and then figuring out what the numbers say about who we are and how we can be better. I work for a fire department, and it’s one of the myriad things I do when I’m not writing or building things or destroying men’s lives with mean things I say.
My last day in Austin, I texted Karl, three date options with the question, “All three of these are multi-hour adventures and then dinner. Is that too much?”
Oyster Dome Trail, 6.3 miles, followed by dinner at Cob and Cork in Bow.
Sugarloaf Mountain and Mt Erie Loop Trail, 4.4 miles, followed by The Brown Lantern Ale House in Anacortez.
Pine and Cedar Lakes Trail, 5 miles, followed by Storia Cucina
On Friday, I flew back from Austin, and Karl texted that he could see I’d put a lot of thought into the options, so he’d put a lot of thought into the selection. Later, he texted back that Pine and Cedar Lakes looked good.
The Date
Part I: The Hike
We met that next day at a park and ride in Burlington, and since I’d vetted Karl online, (yes, he’d definitely written scientific papers, and worked and lived where he said he did and didn’t have a secret wife or children), I decided we could ride together to the trailhead and dinner.
Karl arrived right on time and sprang from his car with vibrancy, ready to hop in. I rolled down the window and asked if he’d mind driving. I’d been traveling so much that I could use a break. Of course, he didn’t mind.
I transferred my hiking gear to his car, and we were off. He asked if I could direct him to the trailhead, and I pulled up the map on my phone so I could navigate. I asked how he was and what he’d been up to. He said just working and not much else. He didn’t ask me anything, so I told him about Austin and my week at the conference. I probed again about how he was, and he said fine. The car was quiet, and he didn’t put on any music (where was John Hiatt, or John Prine?), or ask me anything, and finally, I just sat there in silence, holding my phone with the map and looking out the window.
At the trailhead, I got out and strapped on my bear spray, my hydration vest, and my day pack with first aid kit, rain jacket, and snacks. He stood by the car waiting.
“No water? “I asked when I saw he didn’t take his water bottle from the car, or a pack, or anything.
“I should be fine,” he said.
Wow, I thought, he’s going to do this 1700 ft ascent with no water. He must be in great shape! He’d mentioned many times how arduous his normal work day was, dragging equipment and trudging through water. Type 2 fun, he’d said. He’d described traveling, free diving down, and spear fishing. He’d mentioned being a fast walker, and since he was nearly a foot taller than I, I’d already considered I might need to jog to keep up on this trek.
Within 200 feet up the trail, Karl doubled over, panting and sweating. I asked if he was okay, and he said he was fine it was just quite an incline. I continued on and tried again for conversation, but Karl was barely making it up the hill. He stopped and leaned against a tree. He mentioned he wasn’t used to going up hills. Another couple hundred feet and he was set on a log unable to recover his breathing. He’d been seeing spots, he said.
I imagined maybe he was having a random heart attack, maybe he had a health condition he hadn’t mentioned and now it would come out. I checked my phone for service and considered how we’d get him to the trailhead and an ambulance if needed. I implored him for information. He gave none other than this was just a lot of incline. I finally realized Karl doesn’t actually hike. This was far beyond his ability; this hike that I could have slow-jogged up with my pack on, he couldn’t even walk with zero gear. We were not a match.
“You did pick this hike?” I asked. “You saw the terrain and the elevation gain on the map right?” The man is a biologist. He definitely can read a topo map and an app.
“I just saw there were lakes and thought that would be nice,” he replied.
I thought about how he said he’d be intentional about what he chose since I’d been intentional about planning the day.
Four tenths of a mile into the hike we turned around. Karl could not walk up a hill that he’d chosen for the day, nor did he provide explanation for this lapse in physical ability. I did not shame him. I offered compassion, but I was perplexed.
Part II: the Park with Handsy Grandpa
At the car he suggested we walk around a local lake he knew of nearby that had a flat trail and a park. Yes grandpa, I thought, lets take a walk in the park. Maybe he’ll start explaining things like why he’s not talking to me at any level expected on a date, why he’s completely out of shape but didn’t mention it, or why he drives in the car with zero music despite being a music lover.
At the park we walked, I engaged in one sided conversation. I asked questions like do you know much about the plantlife and follow up questions to things we’d discussed in other meetups. He replied with short answers or a yes or no. I told him about some of my experiences in places I lived like Alaska and searched for anything to get him to share. Eventally, I gave up and we walked in silence next to each other. If I’d had my car, I’d have walked straight to it and gotten in.
When we’d looped the lake he proposed we sit on the grass and enjoy the sunshine.
“Sure that would nice.” I replied thinking maybe the man just doesn’t speak when he’s walking…..or driving. Maybe at rest, he converses.
We sat in the sun and watched boaters. We watched a woman pick a white pencil-thin lightboat off a rack and walk to the water and clip across the lake with precision. A man was near shore teaching his young daughter to row one as well. We both wondered aloud what kind of boats those were and I searched my phone.
Then Karl turned to me, slid in closer, put his arm around my shoulder and leaned in for a kiss, which I received hesitantly but compliantly. I was more baffled that he thought we had a connection than by his forwardness. This was a date after all and trying things out is pretty normal. But what wasn’t normal was not talking to me. Not asking me questions to get to know me more. Not attempting to connect with me on a an emotional or intellectual level. This was not a hookup where connection didn’t matter. This was the building of a relationship.
We had talked multiple times before and what I expected was deeper, more personal information. What also wasn’t normal was not noticing me shrink as he moved in more. I crossed my legs and folded my arms in to my chest and he comfortably moved his body in closer as if I was providing any sign of interest. I was not giving off interest vibes, nor was I interested. I was not flirting. I was not smiling. I was not laughing. He was not funny or charming or even interesting. I had not laughed or smiled in hours. I was bored, lonely, and despondent. This date was a terrible bore. Why hadn’t I driven myself so I could escape? How had I gotten myself into this? It was date three, how had I missed all this?
Part III: Dinner
“Let’s get some food,” I declared. Yes, he was hungry he agreed. We drove of course in total silence for fifteen more minutes to Storia Cucina, parked, and walked in silence to the restaurant. I selected seating outdoors near a heater. It was a sunny spring day and I wanted to at least enjoy the weather.
Karl sifted through the menu. I could see his frustration. I’d already selected a cocktail and was considering a seven mushroom pizza.
“Where’s the food?” he asked to no one as he turned pages after page of the mini menu, flipping aimlessly through.
“It’s right there on the second and third page,” I replied. “Where it says pizza and pasta and ensalada.”
“I don’t have any idea what to get,” he said frustrated. It was obvious he could not adapt even to a menu with a few words of Italian, despite the fact that he knew at least bits of German, Spanish, and French and had a masters degree in biology. He’d peppered me in text with Spanish as we’d discussed my upcoming trip to Mexico and he’d thrown in the german and french words for butterfly and I thought about how I’d provided links to the hikes and the restaurants with menus and he picked this.
“You did pick this,” I reminded. And helped him decide he should get pepperoni pizza and salad because I was clearly on a date with grandpa (who was just four years older than me in regular earth years).
When I ordered my cocktail he said, “wow, a cocktail, really living it up!” I remarked that it was a Saturday night and they had beer and didn’t he want one? Wasn’t this part of the expectation? We’d have dinner and drinks and get to know one another even more after a fun hike up a mountain to lakes?
“Oh no,!” he responded as if he didn’t drink or wouldn’t think of it and I recalled how on the last date he’d had two beers and a beer the first meet up as well. Was I even on a date with the same person? Where was the smart outdoorsy guy who loved type 2 fun and was adventurous? I began questioning my sanity.
“Do you have tattoos?” he asked me. This was only the third question he’d asked the whole time we’d been on the date and it occurred to me with alarm that he was imagining my naked body. I diverted by saying no, but elaborated by telling him all about the tattoos my former boss and friend is getting and how he’s now not getting this Buddhist swoop one that I’m thinking of getting which means it won’t be weird since we couldn’t get matching tattoos because that would be epicly weird.
Karl didn’t laugh at my matching-with-my-former-boss-tattoos joke.
“Do you have tattoos?,” I countered.
“No,” he said. Not no, and then an explanation about his thoughts on tattoos. Just no.
The salads came and Karl got up and switched to my side of the booth without warning or asking for permission. He mentioned it was warmer by the heater near me, as if that warranted him sliding in beside me. Had he asked, I’d have said no. Then hands on my leg. Again, I slid farther away. Then eating his salad and pizza again with no interaction. He ate as if we’d come simply to eat food and leave. I poured my cocktail down my throat like it was a shot because I now really needed a drink. As he continued to slide in closer, I signaled for the check.
“It’s so nice to be dating someone who pays her share of the check,” he said when I asked for separate bills. I brought up the various schools of thought on this debate over who pays, pointing out that men created the patriarchy that didn’t allow women jobs or freedoms and still perpetuates a society where women make less but are expected to maintain ourselves to physically pristine standards. Besides men often show up to the table with little to offer a woman besides money, I pointed out. I simply always pay for myself, I said, because I believe men expect something for their money and I’m not a commodity. I have a job and I don’t need a man, I explained.
“You’d be surprised. Most women want me to pay for everything,” he said. I thought about how little he’d offered me in the last four hours, how I felt like a caretaker, and regretted not making him pay for my time.
We rode back to the park and ride, twenty five minutes, you guessed it, in almost total silence.
I escaped to my car and he sped off. I told everyone I knew about this date. I called James from the park and ride and nearly cried, telling him blow by blow about this experience. He was empathetic. I pointed out he goes out with fascinating women. And this, this is what I get. Men who think showing up is all they have to do.
He reminded me how stunningly handsome and charming he is and maybe he just attracts great women and I reminded him he’s an idiot and this wasn’t a time for humor. He also pointed out how amazing he appears in comparison and I agreed, annoyed. Except it was a time for humor. All day I’d been thinking how if he and I had been on that date we would have laughed our way up the mountain, then snacked at the lakes and gone for pizza and drinks having a marvelous time. How had I so misjudged? I prided myself on vetting men, but did men even have the same standards? Why was this considered enough? How had he showed up so unprepared and put forth so little effort to show me what he had to offer?
Friends were baffled. A co-worker and friend, Chad, said he used to take women up Oyster Dome on the first date to weed out the weak. I should just invite five men all at once and whoever can carry on an intelligent conversation, make me laugh, and make it to the top gets date two.
The Experiment: What the Dick is Wrong with Men?
Over the next few days I looked at chats I’d had with men in apps. I started new chats with men in apps who looked interesting. I noticed how I’d read their bios, ask questions specific to them, then, when they responded, follow up with a relevant narrative about myself and then ask them another question. Over and over, I did this with men asking me almost nothing other than to mention I had great pics. (In the right light, I do look pretty great in a bikini.). However, in many cases, they asked me absolutely nothing. In only a few cases did they really explore who I was or what I thought. It seemed they did not know really how to interact or didn’t have the curiosity or didn’t think they needed to make the effort to gain momentum. Likely, they just weren’t that interested, I surmised. But often they are. And still they often do not interact with awareness. This man, who’d gone to date three had also behaved the same way for four hours. Oblivious of my signals. Oblivious that he should talk to me!
I wondered if it was me. I wondered if I had expectations for men that far exceeded the norm. I thought back to men I dated over the years. I wasn’t wrong. Many of them were interesting and curious and funny. I texted an old boyfriend Mike who Karl had initially reminded me of. Mike called. He was funny. He asked me all about my writing and my hot tub and how I’d built my sauna. He said things that made me laugh. We talked about our thoughts and feelings and the state of the world and the fall of democracy. He made me feel better. I felt connected. I felt like I was talking to a person who could see me. Who understood me. He felt whole. I felt whole. The world flipped itself back rightside.
The Text Exchange
Two days went by without a peep from Karl. That’s when Karl confirmed he’d had no idea what an awful date he’d shared with me. This was normal for him. He texted something about thinking about my crazy hair and how his legs weren’t even sore.
Why would your legs be sore? I thought. We walked .4 of a mile before turning around.
I responded:
“Karl, after Saturday, I needed some time to process the day and my thoughts. I’d like to provide some feedback on what took place on Saturday from my perspective.
I feel like you didn’t show up with a similar level of emotional intelligence, energy or curiosity for me, for the day, and for life in general.
While I researched and planned options, you said you’d put thought into choosing, but chose a hike you couldn’t physically complete and a restaurant where the menu seemed to confound you, despite both the trail and menu available at the links. If you had health conditions or were seriously out of shape, you didn’t divulge any, so I was surprised at the outcome.
When it comes to emotional intelligence, I’d perceived via our first two meetups and phone conversations that you could hold up your end of the conversation and had what seemed to be a desire to get to know me as a person. I think I misunderstood what level of relationships you may be having with women. It appears you may not be dating with the same emotional intelligence I’m used to.
On Saturday, despite my consistent probing for who you are mentally and emotionally, you offered very little about yourself, your thoughts, or your feelings. You asked me little about me or my life and left vast wastelands of dead air in which you should have been getting to know me. Despite lots of softball questions from me, you gave short answers, offered nothing interesting, and left me stuck with a very boring companion.
You expressed love of music, yet we rode in the car for quite some time, both directions in almost complete silence, with little conversation on your end and no music. I was confused by both. A date is your time to showcase who you are and your value. You did neither.
You made physical advances that were entirely unreciprocated, yet you continued to press as if they were mutual. Though I was recoiling with each advance, you behaved as if this was your normal mode of operation, which made me very curious about how you’re approaching intimate relationships. Not checking in to see if a woman will reach for you, but each time moving in as if her compliance is permission is not actual permission. I felt zero connection to you because you had failed to establish one via dialogue and general vulnerable interaction, and I wanted zero physical interaction with you. I was physically turning away or folding myself up each time you moved closer. These were things to take note of and respond with space. I was shocked when you switched to my seat at dinner when I’d given no indication I’d wanted you near me. I’d been recoiling in the park and was just trying to get to the end of the date to get away from you.
At dinner, still wanting to give you the benefit of the doubt, to see if you could turn things around, I’d expected real conversation and introspection. I’d thought we’d sit and talk about meaningful issues and life experiences. I thought we’d have a slow dinner, a few drinks, and really enjoy the evening. You ate quickly, didn’t talk, and it all felt forced and awkward. I’d considered that maybe you’d found the hike a distraction. But what I quickly realized by dinner was that you weren’t interested or weren’t capable of exploring the landscape of who I am; you were simply interested in creating a physical connection. I’d made it clear that without an intellectual and emotional connection, I don’t physically connect.
I was confused by all of your behaviors and lack of ability to reflect and connect with another person on a deeper level. You strike me as someone who hasn’t worked on themselves and learned to converse and show up with the actual emotional intelligence required to date someone like me or to really engage in meaningful, fulfilling relationships. I felt like I was on a date with a teenage boy in the body of an aging man.
It’s important to read the room, and you were not present, nor did you add any value to my day. I came home feeling like I’d been physically violated (though fortunately just a little) and with a level of loneliness one only feels when spending time with someone who has no idea how to connect in a meaningful human way. The experience I had with you on Saturday was empty.
I expect men I date to show up and add real value to my life. I don’t need men. I choose men who are funny, intelligent, fit, energetic, emotionally present, creative, curious, and self-aware.
I think you have a lot of work to do on yourself to offer a woman the kind of value we expect in 2025.
I’d be very interested in hearing what your interpretation of the time we spent on Saturday was, and what was going on in your head?”
Karl replied:
“Hi. Thank you for the text and explaining your feelings. I have not been myself lately. With the states budget crunch, my employment has become a little tenuous. That has affected me greatly, I've had trouble concentrating and being present. On Friday I found out exactly how tenuous it is. I actually thought about canceling with you but I thought it might be good to get outside and spend some time with you. I feel awful about making you uncomfortable but I honestly was not picking up what you were putting down. I apologize.”
Me:
“The first I’ve heard about what you just shared about budget cuts is right now, which is unfortunate. During the 4 hrs we spent together that would have been a fabulous topic to deep dive along with all the issues and trepidations surrounding it—Including how it might be affecting you in the moment. Instead, I had basically 4 hrs of silence and someone who was handsy without invitation.
I would suggest that you be more open and honest about what’s going on on future dates with other women. Based on this experience, I won’t pursue this relationship further. I hope my feedback helps you in the future, though. Vulnerability and openness are going to be your best path to meaningful connection.”
Karl:
“I'm very sorry. I agree with your call and thank you for your advice.”
Harold & Maude
“I’m going to date forty-year-old men when I’m eighty,” I declared to James.
“You’re not really in your 50s,” James, who’s 44, said. “You need to date in your age bracket—the 40s.” He’s been telling me for years how irrelevant our age difference is because I don’t behave my age.
I have a dinner date on Monday with another 44-year-old man who’s into hiking and kayaking and lives on the Island. I’m considering switching dinner to an arduous hike to weed out the weak, as Chad said. Can a man both share himself emotionally and intellectually while moving his legs and asking me questions about me? Should I consider making men pay for drinks when the date is terrible? I refuse to lower my expectations or my standards. I also refuse to have terrible dates and not provide feedback, so the next woman isn’t subjected to a dismal afternoon.
I’ve always been a fan of the cult film, Harold & Maude. Harold was a young man who was intellectually and emotionally curious. He had a dark sense of humor and repeatedly faked his own suicide in grand theatrics to get his mother’s attention. When he met Maude, who stole cars, was an artist, and went to funerals for fun, he saw her wild beauty and fell in love with her despite her impending eightieth birthday. Maude was a woman who’d cultivated herself; she was a fabulous date at any age.
I know I’m going to hear, not all men. And it’s true. But I know so many fabulous aging women and I know just a handful of fabulous aging men at the same caliber, whether married, single, or dating.
From an observation standpoint, the patriarchy has told men that they can show up unqualified and unprepared and put forth little effort, and that is enough (Pete Hegseth). While women are socialized for the exact opposite, and it seems no more evident than in the dating world. At a time when women are choosing either late marriage or no marriage at all, and children are optional, men are going to have to show up with more to offer than a paycheck. We no longer need you.
It’s time for men to be held to the same standards as women. I expect a man to show up and match my energy or at the very least be emotionally vulnerable enough to share who he is and why he’s damaged. I expect men to work on themselves and evolve. I expect men to communicate and be curious about me and about their world. It’s not enough to just show up and it never honesty was enough for any of us. Women just weren’t allowed options. And now that we have them, we’ll choose alone, or time with our friends over men who don’t meet us at our level.
Amy, you have left me astonished, energized, vindicated, and somewhat sad that at age 70, I am finally cognizant of the lifetime of wasted, unappreciated energy I have put into men. One of the few upsides of my age is wisdom, and I wish that I had achieved it much earlier and not put so much thought and energy into less than optimum relationships. Us older women were raised on bullshit Disney and religious expectations and outcomes, which outwardly I was repulsed by but interiorily, gender earworms persisted. I am optimistic that things have changed a bit in favor of younger women and their options for independence and self-containment, while wildly apoplectic about us simultaneously losing legal bodily autonomy via the very worst of idiotic testicular and misogynist behavior. I hope more young women aspire to your spirit and grit.
I have spent the last several decades doing things on my own; a 5 week round-trip cross-country solo camping trip across America in my old Toyota manual transmission pickup (every woman should do this), solo wilderness camping (scarier now these days for multiple reasons), traveling solo to Amsterdam and around America to hear avant garde jazz and other types of world music only to find that almost no women ever seemed to show up, and careers in construction, project management, and similar male oriented, higher paying jobs where the men were not engaged in any type of self-assessment, cultural or artistic concepts, intellectual curiosity, just seemingly satisfied with being empty bro zombies.
Yours is one of the most uplifting, almost surreally satisfying and thoughtfully constructive pieces that I've had the pleasure to read in some time. It is also a stern reminder of how much I have let my physicality deteriorate, and that I need to take better care of me. Grateful for the reminder.
All the best to you, young woman!
Your writing is always great, but as someone who married their high school sweetheart, it's particularly interesting for me to hear about your forays into dating. I've never been on any of the online apps or dated anyone other than my husband. And dates at 14-16 that I vaguely remember several decades later would almost certainly be a completely different beast now that I'm older and I tolerate less BS and I'm a mom and I have my own baggage and they would have theirs and etc etc. The men in my life that I know best are all partnered, and interesting and funny and pleasant to be around. But they're a cultivated, biased sample and finding them through the world of dating sounds like finding a needle in a haystack. I've worked with lots of men who I asked questions of and took time to get to know who never returned the favor. It was obviously galling (given that I remember it), but perhaps less so given that I wasn't dating them.
Your experience with "Karl" thinking he could do the hike while not bringing any supplies or being in good shape reminds me of that poll showing that 1 in 8 men believed they could score a point on Serena Williams. I do have more sympathy for him after reading his response about his job, though. I too have over-committed to events when I was emotionally bereft and suffered for it later.
Also: It is really interesting that you have dated men in their 40s virtually your whole life. I remember, as a teen, thinking that 40 was the peak sexiness of a man. You may have something there.