on the Friend Zone: Good Women Who Made Dirty Friends

This past Sunday, I went to a pumpkin patch with some friends. It was the perfect time to go. The sun was out, the leaves were beginning to turn, and the Bears had a bye week. As we made our way through the apple cider doughnut lines, hay rides, animal zoos, and the rest, I couldn’t help but notice all of the beautiful couples littering the grounds. What followed was a cathartic-like daze. Somewhere between depression and delight. Beyond covetous but not yet quite content.

Relationships are, from memory, warm and cozy. Wonderful things, really. So whenever I get around to ignoring everything therapy has revealed to me about my fear of commitment, I start to imagine the type of girl I’d potentially date. I don’t think of celebrities or ex-girlfriends or girls I’ve merely hooked up with. Rather, I tend to think of girls I’ve liked who simply didn’t feel the same.

As with every man in America—even Ryan Gosling, probably—I’ve experienced several unrequited crushes. My God, are they painful. Horrible. But worse, still, is repeated exposure to a special subset of the unrequited crush. And that is, I believe, of the absolute cruelest variety. Namely, crushes on women who talk dirty. As in, women who are dreaded just friends but who discuss with you in vivid detail their exploits with other men who are not just friends. Avoid this situation because it is hell in its purest form—a constant and excruciating reminder of that which you will never experience. The following cases are culled from my own experience and offered with the expectation that such anecdotal evidence is but the first step in the long march toward a comprehensive knowledge of preventing the “just friends” label. In other words, I hope my notes will help.

In high school, there was one—a very striking girl. Short, brunette, and petite, yet hard to miss. She fit perfectly in my arms, something that I was constantly reminded of because we hugged “hello” and “goodbye” every time we saw each other. Some of the emptiest hugs I’ve ever experienced. Hugs I hoped would someday allow her to realize how maybe she’d really, really like to not stop hugging. 

We were both severely underemployed. I worked at a Jewel-Osco making six bucks an hour, never hesitating to mow my neighbor's lawn for the extra, measly $5 that I desperately needed for my CTA card, while she just didn’t have a job. She had this theory that if you look and act like a celebrity, you would eventually become one. She was funny and outrageous and let me tag along with her everywhere—to parties that were too cool for me, concerts that were too cool for me, and even my own high school’s football games that were too cool for me. What made it worse was that everyone assumed we liked each other, some even thinking that we were a couple. She always gracefully laughed and quickly declined any such possibility, God bless her heart.

She was no prude. She was quite romantically adventurous with other men. And she liked to tell me about those romantic adventures. So I’d listen to these stories of her escapades. And I’d pine. For those who have never endured this torture, how can I describe it? It’s like sitting in a restaurant while the waiter describes all of these mouthwatering specials—then returns to say they’re all no longer available. Oh, and by the way, the restaurant is out of food altogether. And you have to go in the back and help with dishes. And, no, you’re not getting paid.

I was smitten. She was not. It went that way for an entire year until I made out with one of her friends at a bonfire, which she didn’t like. That one fateful night propelled us into entirely different social groups—her, cheerleaders and bros; me, my mischievous group of dirt-stache wearing wannabe-hoodlums. I eventually got over her, moved on, and, well, you know the rest.

When I got dumped by a long-term girlfriend during college, I retreated into a bit of depression. Out of commission for weeks, I happened to look up during class one day only to notice that a brunette was smiling at me. She was the first girl to smile at me in what seemed like forever. She had pearly whites. No makeup. She was gorgeous, the kind I wasn’t used to. She had dusky hair, wispy and cut short around her opal face. She had cheeks that shot into perfect circles every time she smiled. She said so very little that when she did speak I held on to her every word. She was a troublemaker. She made me feel like a troublemaker, too. I was not a troublemaker. I was a wimp who at the time still didn’t know exactly what spark plugs did.

I introduced myself to her. Turned out we were in two classes together. The beauty with no makeup was also in the middle of a bad breakup and I became the poor sap who she directed her ire at. We became good friends. We’d take turns lingering outside each other’s jobs waiting for the other to clock out and then walk to class, envying no one. But, alas, like poorly fenced-in pit bulls raised by angry Cholo youths, the complications of having someone like you back could only be kept at bay for so long. Eventually, I was attacked by the fact that she didn’t like me back. I was attacked and torn apart and, without a passerby to pull me out of the vice-like jaws, I was grievously injured and almost killed. Come to think of it, most of that last sentence was just about pit bulls.

Something had to give. So one summer night, I finally made a pass. It was the worst-planned, poorest-executed pass of my life. She was sleeping over at my apartment, as she did whenever she didn’t want to schlep home. After a bit of awkwardness, she suggested that we go to bed. And while we slept in my room, she kept waking me up to explain how bad she felt about all of this. That she was sorry she didn’t like me back. Though comforting, I just wanted some fucking sleep. I think she took it in a bad way, like I was just done with her, which was untrue. The next morning, we took what can only be described as the quietest walk ever to the Sedgwick Brown Line and parted ways. That was the last we spoke.

I met this last girl during my senior year of college. She was a Sandra Bullock look-alike from Portland. I remember seeing her for the first time and telling myself that no matter how much she didn’t notice me, I was going to notice her. I was going to notice her and I was going to notice her hard. She eventually noticed back and we began to hang out outside of school. We liked to get high and listen to weird music. She introduced me to Tom Waits. She also took classes on human sexuality and enjoyed telling me the content of these classes, including how they related to her life. I’d listen intently over white-cheddar popcorn (her favorite), nod my head, then spend the next half hour digging my fingernails out of my leg.

She had this weakness for musicians and artists. I remember she invited me out to The Mid for a set of this DJ she had been seeing. She hopped up on-stage just to make out with him during the set. He apparently got some Freudian thrill out of it. The sick bastard. The sick, lucky bastard.

What became clear with her and, I suppose, all of the others was that none of these had been emotionally wrenching experiences. Not for them, at least. Awkward, maybe. But it took this last girl for me to really understand: these girls would never like me. It was at once painful and so staggeringly obvious. I should have known. But, you see, dirty girls keep you hanging on. Every dirty hangout. Every dirty conversation. Every dirty story. Every dirty detail. You can’t help but think, “That could be me.”

Mistakes were made on my part. Some were mistakes of vanity. Others of youth. Still, others of the vanity of youth. While it is an absolute certainty that I will make these mistakes again somewhere down the road, I want to share them with you so that you may avoid this entire sticky situation.

Here, my friends, are those mistakes.

Mistake No. 1 – I had, at times, expressed indignation and heretofore unseen emotions when I discovered that these girls had started seeing someone—even though I gamely, albeit futilely, attempted to give off the impression that I didn’t even remotely give a shit. Yes, by my own design I left things impossibly murky and vague—but that was for my benefit. Not theirs! These women were supposed to pine for me, hoping that I’d come around.

Mistake No. 2 – I came around. On last-minute, romantic whims, I’d try to show them how foolish they were for dating these, in retrospect, pretty awesome guys. What was it that kept me coming back when Reason and Practicality were screaming, “Let it go, dickhead!”? (You should know that Reason and Practicality are both very mean.) The heady days of these women falling and falling and falling in love with me were shrinking in the rear-view mirror, and basic logic should’ve dictated that I just give up and move on.

Mistake No. 3 – I didn’t give up. I walked back, and—at this point, I am really taking my cue more from popular music and seventy-five years of American cinema than anything resembling actual human behavior—I told them how I felt, that I was all in, gung-ho. When that blew up in my face, I went right down the street to a bar on the corner. Drank two shots of Jack Daniels, which seemed like the appropriate thing to do. I was in uncharted territory here. Maybe it should have been Jameson. Goddamnit. You know what, I just realized it should have been Jameson.

There’s this universal truth that says when a man starts getting fine tail, there’s a boost to his ego unrivaled by anything else in life. Unlike getting a great job—which, when all is said and done, is still work—dating someone who is interesting and funny can make you feel intoxicated. Blessed, even. Like winning the lottery or even better, finding a massive discrepancy in your checking account. You don’t know why you’re getting all that money, but you keep your mouth shut and hope no one notices.

I can’t say for sure why I kept coming back to the dirty friends. Partly, I think, bad luck. But partly, the maddening fact that these women all tended to be interesting, funny, and a tough crowd. What I can say is that we drifted, these women and I. We didn’t address the issues that caused awkwardness, so the friendships deteriorated. They tried to remain friends. I tried to try. But I had to be honest with myself: I had enough friends. Years later, the memories of those good women who made dirty friends still lingered.

After college, I spent more and more time on the road for work. Isolated for weeks or months at a time, I had the opportunity to think long and hard about where I was at. What I wanted. What was fair. What was right. I also spent a good deal of time thinking why this one restaurant I frequented in Pittsburgh called their signature eggplant dish Aubergine. That’s just way too fancy a word for, let’s be honest here, a pretty shitty vegetable.

The girl from Portland once joked that if we were to hook up, I’d forget about her within six months. I remember thinking instantly that if we hooked up, in 6 months she could very well have been the love of my life. Cue the nausea, vomit that Jack Daniels. The point here, through the fuzzy haze of my closing notes, is that you can dig someone with your entire being, but if they don’t reciprocate, not only is it okay to move on, but probably much, much healthier.

If you’ve suffered through things like this, rest assured that it will change. One day soon you will wake up in the morning, run your errands, go to a bar or party, and somebody there will like you back. Of course, every single one of these encounters will be preceded by feelings of overwhelming dread. But that’s okay! No matter how many hundreds of times I've hardened up and gone for it, part of me is still that confused twenty-year-old “adult” who thinks he's defective. Worse still, the mere whiff of white-cheddar popcorn still brings back all the hopeless feelings I went through during those hangouts with the girl from Portland. And I used to LOVE that shit!