Fiona Apple Week: Breaking Up is Hard to Do

It is difficult to listen to Fiona Apple and not immediately think of break-ups, jilted lovers, unrequited emotions and the like. Many of her songs are heart-wrenching tales of love and loss, of wronging and being wronged.

If you’ve ever been loved or been in love, then chances are, you are also aware of the darker side. Love, unlike what all of the songs say, doesn’t always last. Anybody who has been in a relationship has more than likely also been part of a relationship’s demise, and the emotions that come with it. It is only a tiny fraction of us that fall in love and create a lasting relationship with the first girl or boy we set our sights on. I am no different, and I do not fall into that tiny fraction. I’ve had my tribulations with love the same as everybody else.

One thing I wanted to do with this blog is tell honest stories, to show both the noble and dishonorable sides of my life. We all like to see ourselves as the heroes of our own stories. In fact, we have to, or we will succumb to the whims and woes of the world far to easily. But that doesn’t mean that we are the heroes of everybody’s stories. Sometimes we’re a minor player, sometimes we’re just a plot device, and sometimes we’re the villain. I’ve been all of these things.

I thought about trying to focus this post on just one or two of my bigger break-ups, saving some for other songs and other artists. In considering it, I decided to go for broke and tell all of the stories. Some are small and common, blips on my personal relationship landscape and likely blips on someone else’s. Some were difficult at the time, but in hindsight were not as weighty as I made them to be at the time. Some had to happen, some maybe didn’t, at least in the ways that they did. I am the victim sometimes, but I’m the villain at others. This is a series of honest tales, as long as they need to be. I’m going to spend very little time discussing the particulars of the relationships. I’m choosing only to focus on how they ended.

My first relationship was with Missy. She was my first girlfriend. She was my first kiss. We had a lot in common, and I just spent most of the time thinking about how unlikely it was that someone wanted to be my girlfriend. The end of the relationship had a lot of signs coming before it. As mentioned in a previous post, there was a distance issue between us. Neither of us had a car, and long distance phone calls cost a lot of money back then. We started dating in the August before my junior year in high school, and by January the cracks were becoming pretty obvious. We talked on the phone as much as possible, and in those early days, it was mostly conversations about music or movies or something typically important to two teenagers. We also talked about how things were going in our respective school social lives. By January, her conversations were becoming more and more peppered with tales of a guy named Bill (I think, it was over twenty years ago). My conversations were more and more littered with stories of Jackie and Andrea, two girls among many that I was hanging out with that seemed ti be sweet on me. To say we both saw the signs is a lie. I didn’t, but I’m pretty sure she did. Long distance relationships are not easy, even with all of the ways nowadays to stay in contact. Back then, there was the expensive phone calls and the times we could convince our parents to drive us to the other’s house for a weekend. It wasn’t enough to keep our young minds and hearts from starting to wander. I invited Missy to my school’s winter semi-formal. She came out, and had a lot of fun with my friends, but spent very little time with me. This was also the time she became the first girl that I slow danced with. I knew something was wrong by this point, but I was frankly kind of in denial. The idea of losing the first girl to ever say yes to me was not easy. I didn’t quite have the self esteem to believe it would happen again. I would have let the farce go on for years. Missy was smarter. A few days after the dance, she called me a broke up with me. She was complimentary and I know neither of us had done anything unfaithful, but this needed to happen before one of us did. I was destroyed. I cried all that night, listening to Nothingman by Pearl Jam on repeat for hours. There were no villains in this case. There was one person who knew we had both emotionally moved on, and one person who didn’t. As I look at it today, Missy and I were never quite right for each other. That didn’t stop me from holding a candle for her for way to long. In fact, she was my “failover crush” whenever a relationship ended for more years than I’m comfortable admitting. I’ll go into that a bit more later.

Andrea and I started dating a couple of months later. I took her to the junior prom. I was a stable and caring influence for her to balance out her sometimes chaotic home life. Her father had died years before, her sister and her got along sometimes, and other times hated each other with a burning passion. She had a similar relationship with her mother. But I was different. I cared about her, and listened to her. From the end of my junior year, through the summer and into the late fall of my senior year, I provided something no one else seemed to: someone who she could talk to about her emotional issues. I spent several months being an excellent boyfriend, and was rewarded with a trip to second base. For those of you unaware of the old baseball analogy of dating, I’ll go a little more crude. Andrea’s breasts were the first ones that I got to see and touch. Then we get to November of my senior year. Once again, we have one person who sees the relationship as over and one who doesn’t, except this time I was the one who figured it had run its course. I had noticed a change in the way I felt about her. Just two months prior, I was starting to think about the concept of forever, but soon realized that I was so very wrong. I wanted to go to college out of state. The wheels were already moving on my admission to Ashland University, and I had already tried the long distance thing and found that it did not work. So I did what I thought was the noble thing, I decided to end it before it went any further. I didn’t want to plant any more “first” flags and then bolt for Ohio. I called her up on a Sunday, and using some of the terminology that was used on me months prior, I broke her heart. This time, she was the one who was devastated. I had been a lot of firsts for her just as she had been some for me. The idea of losing something she had convinced herself (with my help) would be forever was too much for her, and she did not take it well. For good or ill, I’m the villain in Andrea’s story at this time.

Andrea’s heartbreak was made worse a few weeks later when I started dating Meghan. It made her feel like all of my “but I’m going off to college and we can’t maintain a relationship through that” explanation seem like a steaming pile of shit. From my perspective, it wasn’t. I did not feel the way about Meghan that I did about Andrea, but that’s not something you can rationally explain to a heartbroken teenager. For any readers hoping I get my comeuppance for breaking that girl’s heart, you are about to get your wish. You see, Meghan was never really into me. She had a crush on her manager at Burger King. He was a couple years older than her, having already graduated high school. He had a car and a job. And he treated her like shit, which was apparently something she craved. All of the work stories she told me while we dated revolved around how much of a narcissistic asshole her manager was, and he treated her like garbage whenever they worked together. But Meghan had a crush on him, and he apparently needed a push to see her as a viable dating option. I got to be that push. Meghan an I dated for just a few weeks, long enough for us to get each other Christmas presents. Eventually, her ploy to get him jealous worked and she immediately ditched me for him in an unceremonious phone call. There was no treatise of “it’s not you, it’s me” or other such platitudes. It was the cold and hard “he finally asked me out, so you and I have to break up.” I should have known. I mean, the three of us went out one afternoon to an arcade, and I was absolutely the third wheel. But I was pretty dense about relationships back then. I got a little smarter as time went on, but not much.

I swore off relationships for a little while after that. I was just a few months from graduation, then summer, then off to Ohio and away from all that I never liked about Central New York. I was so sworn off of romance that I helped my friends Philip and Hillary get together in a Saturday full of back and forth phone calls to the two of them. Philip and Hillary were both friends I made at my karate dojo. Yes, I took karate for several years. I have a black belt. That’s a story for another time. Hillary’s dad was one of the instructors at the dojo. He like me a lot. I was tall and lanky, like him, and he taught me how tall people fight. I’m not sure what he saw in me, but he always seemed to have an attachment to my success. Philip, on the other hand, was not his favorite. He made Philip miserable in class for dating his daughter. I mean, he wasn’t mean, but Philip became his go to example when demonstrating holds and throws for the short few weeks that the two of them dated. In the mean time, Hillary and I had become pretty close because of all my matchmaking efforts. Philip and I were friends for a while before Hillary, and I got to know Hillary pretty well in trying to set the two of them up. This led to a blossoming friendship. Once Philip figured it wasn’t worth all of the hip throws and arm twists to date Hillary, she made the bold move of asking me out. I accepted, since we both had a clear idea of the terms of the relationship. Neither of us was thinking forever, both of us were just thinking of a little time in someone else’s company. The whole thing lasted only three weeks. Her father, well aware that I was now dating his daughter, did not treat me like Philip and seemed genuinely pleased that we were dating. The relationship naturally dissolved, neither of us being hurt or slighted. We went on a handful of mall and movie dates, we kissed a couple of times, getting as far as tongues but never rounding first base. It was fun.

I firmly expected this to be my last high school relationship, but I didn’t anticipate Kate. I met her right after the end of my senior year, and we dated for the whole summer. We even went to Lollapalooza together. I had no intention of continuing it on once I left for college, but caved to pressure from her to keep some semblance of it alive. I think the deal she struck was something like “we’re dating every time you come home, and we’ll see where it takes us.” Again, having done the long distance thing to not-so-good results had me dreading this idea, but to my mind she had also given me permission to explore my college prospects. God, I was an idiot. So Kate and I sort of broke up as soon as the wheels of my parents car left the state, but anyone who knows anything about dating realizes that is not the real truth. More on that further down.

At Ashland, I tried to re-invent myself a bit. I had suffered as the awkward outcast for years in high school, and I decided that those years were over. Unfortunately, you can craft the most interesting history for yourself you want, but if you can’t talk to girls, that doesn’t really help you. I did have a little success. I dated a girl named Kristen for all of a few days. Kristen had a lot of issues. A LOT. It was not her fault, but the result of a horrible past. It still made doing anything beyond talking a little awkward. Kissing was difficult. I never dared to brave past that. I had designs on a couple of other girls after that, but it was Jaime who would successful capture my affections and check another first off of my list. It absolutely wasn’t love, it was all hormones. I was a young man who had yet to have sex, but really wanted to give it a go. She was a young woman who liked to have sex with inexperienced guys, known for better or worse as a “cherry picker.” I guess it can be said that we dated, though no actual dates happened. Mostly we just had some sex. Not as much as she wanted, though. I had to pretty much push her off of me while we were watching Star Wars once. A man has to have priorities. Star Wars is sacred, Jaime was just kind of fun to be with naked. I only get emotional resonance out of one of those. It was pretty obvious to both of us that we weren’t into each other for anything more than the sex, so I broke it off. Also, I was heading back to New York for a weekend coming up, and I still had the deal with Kate (who was really looking forward to my visit). Jaime was a little pissed at me about it. I think her rationale was that she had given me something that no one else up to that point had, so my devotion to her should be absolute. I was of the opinion that, though it was pretty great she was willing to sleep with me, I had a sneaking suspicion that others might want to as well. Also, even though I had nothing to compare it to then, I had to believe that there was better sex to be had. Jaime wasn’t awful in the sack, but I certainly wouldn’t call it good.

In my defense, I planned on permanently breaking it off with Kate as soon as I saw her back home. That was my plan. There were other women back at Ashland that I was starting to make headway with (besides Jaime), and now that I had seen the wider world, I knew Kate and I were not meant to last. That was my plan. That was my intention. Her plan was to wrap her arms around me as soon as she saw me and take away my ability to speak with a long, deep kiss. Then she dragged me to her friend’s house (whose parents were away) so we could have some time together. I should have said something in the car, but hormones kept me silent. Once we got to the friend’s house, I was led upstairs for some serious heavy making out. Articles of clothing were abandoned. Hands roamed everywhere above the waist (I think I may have grabbed her ass once or twice). It’s worth noting that Kate and I had met at a Christian retreat, and both of us at one point had a firm “no sex until marriage” mindset. I had obviously abandoned this idea, along with some other things of my faith, by that time. She had not, and I respected that. I still should have said something before she had her bare breasts in my face. Instead, we just make out and fondled for an hour or so. Once we realized we couldn’t do anything else without crossing her line, we calmed down a bit and returned to a clothed state on the couch downstairs (we had been all over a guest bedroom most of the evening). That’s when I hit her with everything from the past two months. I had kissed other girls, I had “wrestled” other girls in extended tickle fights for space on a couch. I had had sex with a girl. Naturally, she cried. In her mind, I had cheated on her. She had remained faithful in my absence, I had not. I cried to, though not because I believed I cheated on her (even though, yeah, I did). I cried because I had never hurt someone so deeply. And to do it to someone so nice and so pure, that was pretty damned low. She didn’t stay nice and pure for long, as a couple of punches on the shoulder, slaps to the chest, and the string of obscenities that poured from her right then and on the whole car ride home had proven. I went back to Ashland an unattached jerk.

Though I fooled around a bit after that (names like Amanda and Lisa spring to mind), I didn’t actually date anyone until that spring. I had been fooling around mostly with this girl named Heather, and I decided it was time to try a real relationship rather than an endless and sometimes very fun string of hook-ups (most of those with Heather). Heather would later become the last girl I dated, and eventually the love of my life and my wife, but not yet. We tumultuously dated for a few months at the end of the semester, and then through the summer as my college career came to an end after two abysmally failed semesters as a graphic arts major. We did the long distance thing for a few months, but by the fall it had to end. I called it tumultuous, and it was. We had two modes in our relationship: fighting and…sex. Neither of us was mature enough to have the relationship we should have had, especially not me. So, after asking her out officially at Easter at her parents’ house, I broke up with her at Thanksgiving over the phone. There was a lt of screaming from her on that one. She was investing a lot into the relationship, and I was not. Why not? Some of it was that I wasn’t ready for the type of relationship she wanted, and subconsciously I think I knew that somewhere. Some of it was the distance. Once I was back in New York and she was still in Ohio, the times we saw each other, they were mostly about how fast we could get clothes off of each other. When we didn’t have sex, we didn’t quite know how to have a good time together. Mostly, though, it had a lot to do with me being a stupid nineteen year old. I was a pretty stupid nineteen year old. So I broke her heart.

I didn’t really date anybody else for a bit. I fooled around with a girl named Trish. She thought I was bad in bed, and I kind of was. That was all that was important to Trish, so that didn’t last. I messed around with a young woman named Mary Ellen. We both knew we weren’t looking for anything but a fling, so that went nowhere. Between those two trysts, Heather and I made an attempt at “dating” again. It had roughly the same results as the first time we dated. She was invested, I was young and stupid. We had a lot of good sex, but we also had a lot of screaming fights. I wasn’t into it. I loved her, but I just wasn’t able to focus on a relationship that was mostly phone calls. I mean, the relationship existed, but in my head it existed five hundred miles away. When we saw each other, it was great. But we hardly ever saw each other. I exasperated the problem by spending money on my first computer rather than a decent used car. In 1998, both cost roughly $3000, and I made a choice to go with sedentary technology over mobility. That decision precipitated our break up again a couple of months later.

That break up, and some other events, led to Heather and I not speaking for a couple of years. I moved to Ohio, but I didn’t really date. I didn’t have flings either. Sure, I went and got coffee with this little waif I met at Goth Night (stories about Bowling Green Goth Night will happen at some point), but she didn’t call me back because I didn’t make a move on her when we went back to my place. I did try to date a woman named Sarah. That was a disaster that ended not long after it began. Sarah had intimacy issues. We were hot and heavy, and then we all of a sudden she just wasn’t into it. That, combined with distance, and the fact that she had a little girl, made it an awkward few weeks. I had no desire to be a dad, and at the same time didn’t want to give this kid the wrong signals. Sarah had no desire to be alone, and every time she came to visit went from zero to naked groping in a matter of moments. But halfway through she would always just stop. She would go through the motions to finish whatever we had started, but I knew something was wrong. She just wouldn’t open up, even when directly confronted about it. She fed me some line about “hating having orgasms.” Now, I never considered myself a world class lover, but I didn’t think I was bad enough to cause someone to lose interest while doing the deed. I had only had one disappointed lover (that I know of) to this point. I was pretty sure this was a “it’s not me, it’s her situation” when my roommate met the same resistance when they had a drunken rendezvous months later.

The last person whose heart I knowing broke happened about the same time Heather came back into my life. Heather and I were in the process of airing and subsequently burying our differences (most of which were honestly me being a jerk). But at the same time, she was dating a very nice man named Brad. I had no desire to get in the way of anything with Brad, so I started pursuing another girl I had met at Goth Night. I’ve spent twenty minutes thinking about it, but I can’t remember her name. We had a couple of dates, one at Denny’s and one at my place where we watched Labyrinth, after which we ended up making out for a bit. Meanwhile, Heather and Brad had found themselves on the skids, Heather dealing with re-emerging feelings with me, and Brad dealing with trying to rationalize the new, nicer, worthy of forgiveness and humbled me with the asshole Heather had told her stories about. I stayed as far from the situation as I could, being as much of a friend as I could without overstepping my boundaries. Heather, after some soul searching, ended up breaking it off with Brad. When she came to me, looking to rebuild our relationship, only with more mature and healthier pieces, I had to break off what I had going in the meantime with goth girl. It really didn’t take me long to decide who would win that contest. She took it well, and started dating my friend Chris soon after, who was more of what she was looking for anyway. I mean, I didn’t even own a bullwhip, let alone know what to do with one during foreplay.

Heather and I have been together since then. A couple of years ago, we finally got married. That still stands as one of the best decisions I’ve ever made.

But the road was bumpy, as it should be. I had my heart broken, but mostly I was the asshole. Love is a hard concept, especially if you have trouble loving yourself. Another person can never fill that void, although I did my level best to make them try. Only after I learned that was I able to start having healthy relationships. Once I did that, life brought me back to the person who I was supposed to share mine with. But in the meantime, I was not always the gentlemen I planned to be. I hurt people. I disappointed people. I let them down, worse yet if I was the one who helped build them up. But, even though you’re the hero of your own story, you can never be the hero of everyone else’s. But, if you’re lucky, you’ll be the hero of at least one other person’s story.


Mr. Tooduloo

P.S.- If anyone decides to respond to this post with anything about the “friendzone,” just go ahead and repeatedly run face first into a brick wall before you do. There is no such thing, there never has been, there never will be. Understand that sometimes two people aren’t as perfect for each other as they are in your head and move on. I’ve been friends with many women in my life, and some of them I wish could have been more, but never were. But I have never been put in a “friendzone.”

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