“In politics (and love) the middle way is none at all.”
John Adams
(fine, I added the “love” part)
Maybe it’s the geographic location of Chicago, central in its positioning and wedged smack dab in the middle of the country, its relatively mild climate (except for a few subzero winter days), or something else entirely that make the men here so…..well, mediocre.
I moved to Chicago right around two years ago after graduating from a Midwestern Big 10 school (a unique story in Chicago, I know.)
Graduating from college had made me hope that I’d be graduating from something else that had cursed my college existence – the endless cycle of college “dating” that consisted mostly of hookups, half assed “dates” at a cash only restaurant in my small college town, or some weird mixture of a real emotional relationship and regular, drunk sex after bar close.
I was surprised to find out that entering the so-called real world, and the more sophisticated dating life that was supposed come with it, wasn’t nearly what I expected it would be.
During the first few months in the city, my single friends and I took full advantage of the new dating scene. Meeting guys at bars or swiping right on the many new options on Hinge led to drinks on swanky rooftops, happy hours at trendy tapas bars, and birthday boat rides for some (I won’t go into detail on what my friend had to do to get that one. Yes, it involves feet.) College guys who went Dutch on the check at the end of the date were a thing of the past, as was their emotional unavailability! Or so we thought.
Although the dating game seemed to have been elevated, it seemed like the guys we went on dates with weren’t exactly leveling up. Sure, dates were fancier and came with a heftier price tag, and grimy frat houses were swapped out for high rise apartments, but boytoys’ unanswered texts, booty calls and noncommittal attitudes remained. It was the same situation as in college, with a few more years on us and in slightly more urban scenery. My friends and I began to notice that these noncommittal actions were symptomatic of a larger trend from the guys – that of ambivalency, which became obvious in many ways. This half-assery came in different forms, from effort put into relationships to life goals, and seemed to be universal across the dating pool. The overwhelming mentality of mediocrity from these men, and their willingness to be content floating somewhere in the middle, seemed to be irrespective of career, salary, education level, or other factors. In fact, the only thing these guys had in common is that they were born and raised in the Chicago area.
I know what you guys are thinking, and maybe I have been on one too many dates at the Hampton Social with subpar guys who have made me write off all men in Chicago as average and noncommittal. But allow me to elaborate! As a relative outsider to the Midwest, I like to think that I’m better able to see the differences between Midwestern men as opposed to men from other parts of the country. Living in different cities has exposed me to all types of regional differences in culture and ways of life, and twenty something men are no exception.
While I’m not trying to reduce the men of a Chicago to one single cliché, there were unmistakable trends that my friends and I picked up on from each of the guys we dated, hooked up with, or sugar babied (for legal reasons, that’s a joke), all which seemed to be rooted in an ever frustrating “middle of the road” mentality. While the specifics are obviously exclusive to mine and my friends’ experiences, this trend is a commonly felt annoyance from many women all over the city – so much so that Overheard in Chicago has started making memes about it. Without further ado, the following are the most apparent patterns in the mediocre mindsets of some of the eligible bachelors of the Windy City:
Moderate beliefs
By “moderate,” I’m not necessarily speaking in a political sense, although many of these men certainly fell into that category. Many of the guys I dated believed in certain values and ways of life that didn’t take to one extreme, but were often contradictory. Collin was one such guy.
Collin was a seemingly opened minded and relatively progressive guy – he laughed at my feminist jokes, had grown up in a blue semi-urban area of the Midwest, and encouraged frequent use of the c*** word (the bar is low, I know.) He was also an avid traveler who could hold an interesting conversation about more than surface level deliberations of if Will’s or Ranalli’s was a better Badger bar – all signs pointed North.
We got around to my favorite make-or-break first date question: who did he vote for? He immediately avoided eye contact and took a sip of his drink. “I……didntvoteinthelastelection.” I was utterly confused, and went on to prod him with follow up questions – did he not believe in women’s rights? Did he care more about the economy than sexual assault victims? Was he a closet racist? I’m really fun on dates, clearly!
His answers were no, definitely not, and why would you ask me that? But his perspective was clear – Collin, like so many Midwestern men I know, had fallen into the trap of hypocritical political views – you know, the “social liberal, fiscally conservative” group? So many of these guys believed in, say, a woman’s right to an abortion – but then completely fumbled the bag when it came down to putting someone in office who could actually make it happen. Maybe they liked being perceived to their friends and potential partners as someone who wasn’t a homophobe, but when it came down to it, helped usher in someone who was exactly against that. This might also just be indicative of men’s’ inability to take any accountability for their actions, but that’s another blog post in itself.
What I’ve found is that so many guys in Chicago can’t seem to decide between conflicting values in what they want for their own life plans.
Nico was a CPA who, besides choosing a decidedly average profession, was surprisingly interesting – he had a unique perspective of the world, was genuinely fascinated by math and numbers (hence the CPA title), and spoke his views with conviction – a refreshing wake up from your basic Big10 bro who thought liking The Office was a personality trait. He had voted who I voted for, and finished my sentences about the vicious cycle of the modern prison system – our political views and metaphorical stars had never seemed so aligned.
We were discussing far-out future plans and what we hope our respective lives to look like in 10+ years. He mentioned the possibility of starting his own accounting firm, and wanting at least three kids by the time he was thirty-five. “Three?” I joked. “Your wife will have to stay at home for a year just to recover from that.” To my surprise, he responded that yes, he did indeed expect his future wife to abandon her career in lieu of stay-at-home motherhood.
Everything he had just said about the power of the pussy evaporated into thin air. How could he possibly claim to be a champion of women and expect his future wife to give up her needs to tend to his unborn children? He rushed to explain that he planned on being an involved dad (famous last words), and that of course he’d love for her to stay at work, but that he did expect his wife to prioritize family needs above all else. If she was able to balance her career and social life too, then great! So long as it didn’t take away from devoting her spare minutes to tending to their kids.
I couldn’t believe what I was hearing – it was as if he supported shattering the glass ceiling only when it didn’t inconvenience his dreams and his own life plans. This odd combination of pseudo feminist and the husband from Sister Wives, and worse, his inability to see anything wrong with it was incredibly offputting. I never saw him again.
I’ve seen this conflicting medley of seemingly modern values and age-old sexism read its head many times. Whether it’s a guy who says he’s not intimidated by a women’s career but resents her when she makes a bigger paycheck, or the guy who wants a girl who isn’t “easy” but wants her to try anal after the second date, it seems like Chicago guys are perpetually in the middle of two extremes, including what they say they believe and what they actually do when push comes down to shove.
Turns out, I’m not as good of a judge of character as I think I am.
Room-Temperature Personality
There are many a Basic Bro in Chicago that can be found lurking in their natural habitats of various Old Town bars and the patio of Federales. What’s a Basic Bro, you ask? Only the most commonly encountered personality type of a guy in the 606. Basic Bros have strikingly similar personality traits that make them almost indistinguishable from one another. The label of Basic Bitch is thrown around as an insult to women, but the Basic Bro is rarely speculated as closely.
While some of the typical Basic Bro qualities include working in finance or accounting, owning an arsenal of Patagonia fleeces, and having been a part of a social fraternity in college, Basic Bros aren’t exclusive to stereotypical white frat boys. They’re indicative of an underlying “type” of most men in Chicago. If the stereotype of a Brooklyn boy is his vintage jeans, reusable farmers market tote, and Birkenstock’s, then the Basic Chicago Bro is unadventurous, small-minded and honestly, boring.
The Basic Bro rarely deviates from the norms of what they think a 20-something guy “should” want – an endless supply of girls to hook up with, making more money than he needs, and rarely venturing outside his comfort zone. And why would he? Despite their lack of interesting personalities, most Basic Bros have a steady streak of desperate girls’ Snapchats at their disposal during all hours of the night. But, I digress.
Most of the Basic Bros I’ve been on dates with don’t see a problem with the fact that their only friends are former college roommates who are almost exactly like them, which can also be seen in their larger social circles.
Basic Bros don’t feel the need to step outside their small bubbles or try new things because they’re, well, comfortable there. When asked why he chose to work at a major investment bank 6 days a week, one date struggled to find any other response than, “Because I make a lot of money?” I couldn’t tell if it was a statement or a question. He also couldn’t seem to explain why he had followed in his father’s footsteps to become a CFP, only because it was the thing he thought he should be doing. This same guy had also never tried Thai food because he thought it would be too spicy, so that was probably a red flag in itself.
At an apartment party with a guy who I liked reasonably well and had gone on a fair share of dates with, one of the guys’ acquaintances made a mildly offensive sexist joke as I was standing in the kitchen (perfect timing on my part). I looked at my date for backup; he awkwardly shrugged, avoided eye contact, and said nothing about it. It was clear that he didn’t want to do anything to disrupt the delicate balance of the party mood, and he left me to fend for myself. I eventually realized after a few other similar incidents that this guy was never going to speak out or stand up when the situation warranted, because he was too afraid to be on the outskirts of everyone else.
Disappointingly, many other Chicago men have adopted this mindset – from refusing to venture out to a new part of the city because they’ve never been (not sure how the logic in that works) to not questioning why they’re on the path that they are, it seems like being “one of the boys,” or really, one of the crowd, reigns supreme over everything else.
To put it simply, Basic Bros are a little too cemented in their comfort zones to venture out of them and a little too happy to be stuck there. Whether they got there by their own accord or what they thought others would think, I’m not sure. All I know is that I’m sure as hell not going to be the one to chisel them out.
And finally….The “half-relationship”
Finally, the one you’ve all been waiting for! Of course, I’ve saved the worst and most applicable one for last. The dreaded half relationship is relevant to many guys and girls of a certain 20-something age, but something Chicago guys are notorious for.
The “half-relationship” is something that likely isn’t a newfangled idea to any Millennial woman in Chicago, but for those lucky enough to have somehow avoided this arrangement, I’ll elaborate. This “half” or semi-relationship is a delicate hybrid of certain characteristics of a serious relationship, like emotional intimacy, combined with parts of a not-so serious one (irregular communication, flakiness – you know the drill) This can result in a confusing and distressing situation.
If you’ve ever hooked up with a guy in what was supposedly a no-strings-attached situation, but felt yourself getting jealous when you saw his Snap story with a mystery girl at City Winery, then congratulations – you’re officially a part of the semi-relationship club! As president, I’d like to formally welcome you in.
The half relationships that are an unfortunate but essential right of passage in our twenties more often than not start out fun but quickly turn sour. The lack of labels is something I’ve found that guys in Chicago wield as a tool to avoid the obligations of being in a relationship. From standing up dates to not going down on you, the guys in Chicago will use the guise of a half relationship to be void of responsibility for hurt feelings that result from their actions.
Yet, the reason we end up being so hurt isn’t because we couldn’t accept the guy’s desire to be considered single. It was because, despite forewarning us of his inability/unwillingness to commit, the guy’s actions seem to contradict the half relationship status he himself had insisted on. My friends have countless stories of supposed fuckbuddies telling saying they were in love and wanted to move past the “talking phase”, only to be ghosted after three months of seeing each other.
While I could list the countless amount of times this has happened to me, one guy in particular demonstrates how Chicago guys are professionals at using the half relationship status to avoid commitment by way of mixed signals and gaslighting.
Jack was a slightly older investment banker from a small town in Wisconsin who had recently gone through a breakup. As such, and for what I thought was good reasoning, he didn’t want to jump headfirst back into the dating pool – at least, that’s what he said. At the time, I wasn’t sure if I was too interested in going on more than a few dates with him, so I played along. But, as they always do, things escalated quicker than expected. It only took about three drunk hookups for him to start texting me consistently and ask to hang out at every waking moment. Only about a week after we met, he texted me after bar close and asked to come over at 3am because he missed me. I thought it was cute but strangely conflicting with what he had established as a non- relationship. Even so, when he went on a road trip to Indiana with friends the following weekend, he blew up my phone with missed FaceTime calls saying how he wished he could have stayed back with me.
I was slightly wary of his intentions, as he had made sure to tell me on our second date that he had zero intentions of dating someone seriously so soon after his breakup. Yet here he was, doing everything a boyfriend would do (and probably more.) So, I threw caution to the wind, told myself to stop obsessing over what we were, and got on the half-relationship train for a few months.
For all intensive purposes, it felt like a real relationship. We hung out constantly, talked on the phone for hours about nothing, met each other’s close friends, and talked about the “one days” of the future. Sure, we didn’t have a label, but I didn’t think we needed one – it seemed like the half relationship train was headed one-way to an exclusive status.
Even after a few months of acting like boyfriend and girlfriend, I neglected to define the relationship at the risk of being branded high maintenance and having my “chill girl” title revoked. FYI, the “chill girl” trope is another facade designed by men to avoid accountability for their actions.
I didn’t prompt him to have “the talk” until a few oddly quiet days where I hadn’t heard from him at all. I knew he had been really stressed at work, so I figured I’d let it slide. Ladies, I’m sure you all recognize the feeling in your gut where you realize it’s over, but don’t want to admit it to yourself yet? That’s where I was.
Four days after complete radio silence, I asked him to hang out and received no response in return. Forty eight hours later, I asked him if everything was okay, to which I received a vague and unconvincing reply that things were “fine”. After about a week and a half of him ignoring my texts to talk or hang out and essentially dropping off the face of the earth, I attempted to salvage the “relationship” via a shit storm of texts, at the very least to get closure (which I think we all know is a myth.) I told him that his behavior was completely unacceptable, and that after months of consistently hanging out and being effectively together that his actions made no sense – this wasn’t a one night stand, for crying out loud! We had shared real emotions and parts of our lives every day for the rememberable past few months. He needed to either put in the effort, or walk away altogether.
Guess which one he chose?
While Jack may have thought it was noble to refrain from calling me his girlfriend so that I wouldn’t mistake us for something serious, his boyfriendly actions spoke volumes louder than his words. After months of acting like we were in a full blown relationship, in our final conversation, he ultimately used the fact that we weren’t technically “official” and that he had preemptively told me that he didn’t want a girlfriend as an excuse for his shitty behavior. Even though he had been the one to initiate pushing our non-relationship past the boundaries of a hookup, in his mind, the decision to ghost me out of nowhere was completely justified because, guess what – we weren’t dating!
(Two weeks later, he started seeing a girl from his hometown, which explains the abrupt ghosting. I wonder if he’s only half dating her, too!)
It seems to me that the guys in Chicago want to have their Portillo’s cake and eat it, too – they want someone to give them head, listen to their mommy issues, and bake them cookies, but god forbid the person doing it thinks they’re any less disposable than a razor head. Whether the guys in Chicago actively or passively establish the half relationship status, they do it to avoid being held responsible for their contradictory and confusing behaviors, and for what? Of course, the freedom to swipe into oblivion on Hinge.
Men of Chicago, please turn off Wolf of Wall Street and take a hard look in the mirror the next time you consider putting a qualifier on what might already be a relationship.
********
Living in a city full of men who teeter between halfway in and halfway out of the metaphorical doorway of dating can be exhausting – you never know where the guy is going to land on his viewpoints, personality, or how involved he wants to be with you. Chicago guys’ refusal to take a firm stance on one or more of these things can entrap you in a dating game that seems to be rigged so you always lose.
The worst part of all is that these guys are a little too ok with just being okay- they’re just too darn comfortable where they are to make an effort to move themselves or the relationship past the halfway mark.
Whether it’s due to the GPS coordinates or another factor of the Midwest metropolis that causes this mentality in Chicago guys I can’t say for sure – but from my own experience, the middle ground rarely leaves either party satisfied, in both relationships and politics.
Especially in Chicago’s dating scene, sometimes there’s no such thing as a happy medium.
Xo,
Sasha