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A Note to Chicagoans: Life as a Loser is coming to your humble dwelling, this Saturday. Details can be found here. You should come. Come.

A Note to Everyone Else: The Life as a Loser series is ending at No. 200, which will run on March 29.

There are now four left.


No matter what the social situation, everybody always wants to hear my story of being on Win Ben Stein's Money. (If you don't know the story, you're coming to


the party somewhat late, but that's fine; I highly recommend reading: "#1: INTRO TO LIFE AS A LOSER." If you don't feel like wading through, here's the short version: Then-fiancee breaks off our engagement hours before appearance on Comedy Central game show. Hosts of said show mock me on national television. Fiancee leaves days later to hike through Appalachian Mountains, never to be seen again. I begin to write. That's where we are now.) Years have passed, and I've honed the story down to its maximum level of efficiency: I can now tell it in 45 seconds in radio interviews.

(I've been doing a lot of radio interviews recently to "promote" the "release" of my book, which has the same name as the title of this column, mainly because, save for a couple extra columns and some savage re-editing, it's pretty much the same shit. Buy it anyway.)

I'm no longer sensitive about telling the story, because it has been so long and been told so many times. It not as if happened to someone else; the scars are still there. It's still my story, the driving influence. It's just that I recognize its value as a story now. I pause for dramatic effect at the right times, I nail the punch lines, I hit all my marks. People hearing the story for the first time never know what to think when it's over; is he really that OK with it? Is he really comfortable with this being cocktail fodder? Or is this just part of his schtick, the "loser" guy doing his thing?

If you don't stop scratching that, it'll never heal. For the last couple of years, I've simply used the story just as a wacky introductory anecdote. I wasn't really scratching it. I haven't really gone back and looked at how it effects me now, other than as a glib pop psychology ("… and that's why I started writing a Life as a Loser column. fin.")

But even though I stopped scratching it, it still hasn't healed. Maybe it's time to take a look at why.


What's most important to realize about my ex-fiancee leaving me that day five-and-a-half years ago (jesus) is that she never came back. One day we were four months away from a wedding, the next day we weren't, and the next day she was gone and I never saw her again. Her explanation at the time was hazy, and that her exodus makes more sense as the years have passed helps me now, but not then.

We were, after all, only 21 years old. In retrospect, I can't imagine what we were thinking. Neither one of us had jobs, and neither one of us had any real plan other than "let's get rich and famous." Of course, when you're 21 years old and just graduating from college, having a "plan" isn't really on the radar. Why would it be? I suppose one of the reasons we decided to get engaged was that finality that graduation promised; the end of the school year happened to be coming at the peak of our relationship, when everything was perfect and impenetrable, when nothing could go wrong. We couldn't exactly just break it off, could we? Her parents had met in college and gotten married young; my parents had met at drunken party and done the same. We were just doing what seemed prudent, what seemed obvious.

Is that a reasonable explanation? I'm just asking, because people look at me like I'm crazy when I tell them I was engaged at 20, like I'm a mountain Ozark or something. It made sense at the time, I think.

So I was stupid and young. That's a given, and I get it. But that doesn't help explain why it still hurts a little, why I usually skip over that part of the photo album. I certainly am not still pining away for her. I don't even remember her. Isn't that strange? I can't recollect what attracted us to each other. I was a newspaper dork who was way too into Nirvana and baseball and got paranoid when stoned. She was a Phish hippie chick from the south Chicago suburbs with an eyebrow ring and a tendency to wear sarongs. I can barely even come up with any landmark experiences we had with each other that are any different than your typically boring college life. I don't remember what her favorite movie was, or what cereal she ate, or what her best friend's name was. It's not that I've blacked it out; it's just that, deep down, I didn't care enough to mentally catalog that anywhere.

It's not that I even have much curiosity to see how she turned out. As far as I'm aware, she doesn't know anything about her mythic status in these columns or in the book. That seems strange too. Surely she's heard of Google? She'd have to know something, right? Maybe she knows all about the columns but considers me a freaky ex better off ignored so things don't get scary. That seems awfully possible, now that I think about it. But as for biographical information about her, I know she's married and that she lives in the Chicago area. I don't think I need any more than that. It's not as if I she had some big dream in life which I wonder whether or not she accomplished. (Though maybe she did; I might have forgotten that too.) I just don't think about her that much, other than in the context of these columns, how she ties in with the overall story, how the whole experience inspired me to start this series. The only reason I'm thinking about her now, I guess, is because the columns are about to end and I feel an obligation to wrap the story up somehow.

But that's underselling it. When I think back, before her, I don't remember feeling particularly self-conscious or insecure. I only dated two women -- girls, really -- before she came around, and, frankly, I was kind of a jerk to both of them. I didn't cheat on them or anything, or treat them badly. I just found their personalities somewhat irrelevant to their place in my life. I had a girlfriend! I was having sex! What more was there? That's a side effect of my age and immaturity at the time, of course; it was so early on in the relationship process that I didn't really analyze what I was doing that much. I never feared they were sleeping with other guys, or that they thought my penis was too small, or that I was going to get fat and they'd find me unattractive. Those insecurities just weren't there. In short, I never invested myself in either one of them to be too open or vulnerable; they were my sidekicks, my partners in the fight against, I dunno, my parents maybe? That was it. That might sound mean, but, hey, we were teenagers: I bet they felt the same way about me. Why wouldn't they?

In fact, I wasn't particularly neurotic around her, not that I can remember. We were just your typical college couple: We got stoned together, we left with each other after every party, we fucked, we went to the diner all hungover together the next morning. I remember being simultaneously freaked and intrigued by the fact that she'd once had a lesbian experience, but that was pretty much it. I guess that makes sense; if we had analyzed things too deeply, maybe we would have figured out that we didn't want to be together. Truth be told, that's probably what she eventually did. She just beat me to it.

But after she left, that all changed, and fast. I became too clingy to every girl I dated, too insecure, too much of, as the current parlance might put it, a whimpster. Everything about me seemed wrong. All that I had valued about myself seemed stupid. Eccentricities turned into character flaws. Any cocksure element of my personality vanished. I became the guy at parties who sat in the corner and complained to his female friends that he couldn't figure out why nice girls didn't like him. I found myself suspicious of my friends, thinking they were secretly contemptuous of me, or, worse, dismissive. I started feeling like I was fat. This is perfectly natural for someone who has just been kicked in the nuts by a failed relationship. I don't think it's supposed to last five years, though.

No one else had made me feel like that. No one else had made me spend my year in Los Angeles, 100 yards from the Pacific Ocean, drinking cheap wine and chain smoking on the balcony, reading sports magazines and talking to no one. Even then, when I thought about her, it was in vague, how could she? terms. I didn't miss her; I missed how I felt when she was around. That had nothing to do with her, I recognize now; it was, like everything, 100 percent me.

You see, the thing is … it's just that she was gone. In a flash, really. At one point, my life had order, had a mission, had a purpose: Marry this girl. Whatever flawed the logic, however specious the postulate might have been at its core, that was the driving force behind everything. In the span of days, that vanished. And so did she. It couldn't have been more jarring than if she'd been hit by a truck; I had this, now I don't, now what? And that I never saw her again, or spoke to her, made it that much more apparent: Everything can change, immediately, and you will never have had any idea that it was coming.

That's what the ex-fiancee did. It wasn't her, it wasn't who she was, it wasn't even that she didn't want to be with me anymore. It was just that she was gone, and I had to reconstruct everything, on the fly. My unquestioned reality had evaporated, and I had no one to offer any answers but myself. And my answers always ended up having something to do with how much of an idiot I was. How it was my fault. How I could have done something different. How I had no fucking idea what I was supposed to do now.

This led to some pretty awful relationships, which basically consisted of me asking girlfriends why they were with me, why they would lower themselves, how I could change to be more like what they liked. I've got a number of irrational fears that I'd like to share with you. This would go on until they got tired of it and dropped out, which just perpetuated everything I already thought. And repeat.

That was the legacy of the ex-fiancee. That's what lead to this, and the column, and the whole series. That attempt at reconstruction. It has taken a very long time, but I think I might be getting there. I'm currently in the longest relationship I've ever had, including the ex-fiancee, and I don't spend every second wondering whether she secretly hates me, or whether she thinks I'm too fat, or whether she'll just vanish into the nether when I'm not looking. It's a battle I had to fight in my own head, and it had nothing to do with the ex-fiancee or anybody else. At least I hope not. Otherwise I'll just have to go through all this shit again and, frankly, I'm getting a little old for such silliness.


People often ask me, sometimes in those radio interviews, what I would do if I ever saw the ex-fiancee again. The easy, short answer is probably the correct one: I'd run. Fast. Otherwise, I might start scratching again.


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