Several years ago, I was devastated when my serial monogamist—yet ultimately commitment-phobic—boyfriend of three years broke up with me. I’ll call him Shane.

After getting dumped, women often try to make themselves feel better by making small changes in appearance; perhaps buying shoes or getting a new haircut that says “look what you’re missing out on, motherfucker, did you know my hair could have this much volume?” I, however, took things many steps further in my search for female empowerment: starting with a new hairstyle and ending in cosmetic oral surgery.

I was dropping pounds due to my loss of appetite, which I couldn’t have been happier about. I changed lipstick shades, and began whitening my teeth. While the whitening was indeed brightening my smile, unfortunately it also accentuated some staining on my front teeth, which I’d been meaning to get around to fixing for years. In the past, I’d had them bonded, but that was only a temporary solution and the stubborn stains would always break through; I knew the only permanent answer was veneer caps. I’d been avoiding the complicated process, but now felt ready; it would be the final step in my post-Shane transformation.

My ex actually talked me out of the procedure when we were together, telling me my teeth looked fine. And I had trusted him. What was I thinking, taking dental advice from an Englishman! Only Americans understand the true value of a beaming smile and they’re the only nationality to be trusted in terms of dental care.

The exception to the rule was my orthodontist in Junior High, whom I blame for the whole staining situation in the first place. I think the braces themselves, when removed, took some of the enamel off my front teeth. Of course I’ve considered suing Dr. Davis many times, but he was a beacon in our community and a deacon in our church. Yet he practically robbed my family blind, insisting that all four of us children needed braces in a serious way or we would end up in the circus, each and every one. He tried to up-sell every new-fangled dental procedure in the book to my gullible mother, praying on the entire family’s insecurities to get to my dad’s wallet.

When I was no more that ten years old, both my sister and I were fitted with a palate expander that could have doubled as a medieval torture device. Each day my mother had to reach in and turn a key in a metal contraption fitted to the roof of my mouth, in order to slowly expand my upper palate to a more average size. It was extremely painful and she hated to do it, but insisted that Dr. Davis only wanted what was best for us children.

I wasn’t so sure. Was I the only member of the family that could see through this man? His smile, though wide and white, did not seem genuine.

And already he was making big mistakes. A huge gaping hole appeared between my front teeth—a gap twice as wide as David Letterman’s on a much smaller head. The same thing happened to my sister.

“Of course,” the doctor bellowed nervously, “this is perfectly normal as the palette has to be overextended in order for the teeth to eventually fall into their natural places. The gap will close within a couple of weeks, and until then, heh heh, you kiddos will just have to stick a chiclet in there and hope no one notices. Heh heh hum.”
A couple of years later, the braces went on. Wearing braces is uncomfortable in itself, but what I found much more excruciating was having to sit in that chair for hours at a time, and listen to the orthodontist give me updates on his daughter. She was a year ahead of me in school, a pretty blonde.

“Angela just got inducted into the National Honor Society; she’s a real smart cookie, that one. Heh heh.” I would come in every two weeks for three years, with my lips stretched out and my tongue drying out, gasping for air, while he would update me on her latest accomplishments.

The following appointment: “Angela just moved up to third chair in band; that little munchkin really has a natural talent with the flute. The kid’s got spunk.”

I wanted to give him my own updates on dear Angela, whose reputation was quickly diminishing, but I couldn’t with a mouth full of cotton. That’s just swell, I wanted to retort, I heard Angela got so drunk on Saturday night that she ended up sleeping with David Magruder and then later playing Scott William’s “flute” pretty well in his woodshed, if you catch my drift. She really is getting around this year—that Angela does have spunk!

I, myself, was running track, working on the yearbook, and on the cheerleading squad. In general I was doing just fine—a well-adjusted teenager—but in the dental chair I was reduced to a vulnerable, insecure kid, at the hands of someone else in the name of self-improvement.

The braces finally came off, end of junior year. The week before my final appointment, Dr. Davis called my mother and I into his office and closed the door. I thought my smile looked great, but he wasn’t convinced that my transformation was complete. After all, he had four years of college to think about for dear Angela. Though happy overall with the result of the orthodontics, Dr. Davis still felt I had what is referred to as a “gummy smile” in layman’s terms, and suggested a surgery to break the jaw to eliminate that lifelong flaw. He said his own son had had the procedure and he hesitated to imagine how he would look today had he not.

Finally, thankfully, my mother drew the line. “What was that all about?” she said in the car. “I’m beginning to wonder about these orthodontists, and I don’t know about you, but I think Dr. Davis’s boy has been ugly since the day he was born and no amount of surgery will fix that!”

Twenty years later I wanted to undo all the dental damage done to me over the years. The timing seemed perfect as once again, after the break up, my self-esteem was suffering at the hands of a middle-aged, disingenuous man.

When Shane told me over coffee one afternoon that he wanted to end our relationship, he explained that something was missing… some indefinable little thing that he couldn’t put his finger on.

I could put my finger on it, and thought to myself: What’s missing is your soul, you heartless, hairy, used-up, crumpled up, piece of Eurotrash.

Though it seemed unexpected, in hindsight, there were red flags. But blinded by domestic bliss, I ignored them. Our routine was constant and comfortable and can be best illustrated by our morning coffee ritual. The process was like having a snooze alarm because there are three distinct steps in using a French press, and we would sleep between all of them until the coffee was ready. He would pour the coffee while I would feed my dachshund, Frankie. She would inhale her food and then jump back into bed with us as we were reading, which we would do for about an hour. Each morning Frankie would let out an incredibly human-sounding belch after making the leap to the bed on a full stomach. You could set your clock to it. Each day we would laugh. Each day we would have coffee together. Each day she would belch. Each day we would smile all cuddled in bed together.

When I woke up the first few days after the break up and slowly came into consciousness, reality would rear its butt-ugly head. “Why do I feel like shit today?” I would ponder. “Why is mascara running down my face along with dry eye goo? Why is my pillow wet with sweat and why do I feel like I’m gonna projectile vomit?” Then I would remember.

Crying daily on the phone to my parents and each sibling, I appreciated having a big family so I could spread myself thin. I tried to hold it together but would be in mid-to-full sob by the second sentence. At times my speech was completely unintelligible, interrupted by massive intakes of air and then explosive cryarrhea.

After work I would usually go hang out at my friend Georgette’s and blubber some more. I would flip numbly through magazines, while staring trance-like at reruns of Sex in the City, which caused me to tear up. “They’re so real!” I would say; “that one really got me. Carrie is conflicted and having some deep thoughts, Georgette, and that shit happens.”

Alone in my apartment, time seemed to move backwards. While watching TV I’d think: I can clip my toenails; that will kill five whole minutes. I could clip Frankie’s, which would kill ten more. That’s fifteen minutes that would pass and I’d never have to exist in them again.

I knew it was time for some changes—any little shift to make my new life different, so it didn’t remind me of the old one. I tried instigating positive habits to replace the bad habits that had gotten progressively worse since the break up. I joined a gym, got cable television, and briefly tried therapy and meds.

Then came the physical changes. Without doing much research, I chose a dentist in the East Village. Thus began the two-week process: sanding down the existing front teeth a bit so the caps can fit comfortably, taking molds, and creating temporary caps while the veneers were being made. Not overly-thrilled with the results, I felt the teeth were a hair too long. They were also a half-shade darker than the surrounding teeth, the dentist explaining that I was in between shades so he had to go darker. Weird, I thought, You’d think he’d want to err on the brighter side.

Even so, I was flashing smiles to anyone who would give me the time of day, out-smiling even the mentally ill. Until a week later, when I was biting into a Cuban sandwich at the office and had a panicked feeling that I had left something important behind. I used my tongue to double-check and sure enough there were only nubs. The culprit was not a crispy apple, not a cashew nut, but bread—somehow the bun had created a high-suction-force-field that pulled both the teeth right out. I had to dig through the buns to find the valuable caps. It was humiliating to walk around the office that day. “I’m ssshhhorry you all have to ssshhhhee me like this,” I muttered, head bowed.

Back in the dental chair again, I squirmed as my dentist apologized and explained that perhaps the cement had been faulty. He reapplied the troublesome teeth and warned me to be more careful. Which seemed impossible since I had mostly been eating yoghurt and berries due to my post-break-up lack of appetite. The sandwich had been a splurge—and a risk I never should have taken. I decided to take berries out of the mix because of their dangerous seeds, and only drink things from a straw.

In the following weeks I tried to keep up with my new routine, working towards a semblance of normalcy. I was down to crying once a week, and less loudly.

I managed to get out and about, and was looking forward to a visit from my brother, David, and his fiancé, Kara, whom I was meeting for the first time. Not long after their arrival, we headed to a pizza joint. Deep in conversation, I bit into a slice of pepperoni, and once again felt my teeth dislodge, mid-chew. “Oh ssssshhhit; I’m sshhorry about that,” I said, as one skipped across the edge of Kara’s plate, following the other one across the table, bouncing onto the floor. “Let me just sssshhhlide under the table and take a look-sshheee.” My eyes welled up with tears. “David,” I continued, “Would you mind joining me down here a sshhhecond because I can’t find the capsssshh and they’re really cossshhtly.”

All three of us ended up under the table searching until we found them. I got through that meal, practicing my closed-mouth smile. Next morning, I was back in the dental chair. This time, he blamed me, accusing me of grinding my teeth at night. I found this odd since both incidents occurred while I was eating, not sleeping. Convincing me that getting a mouth guard was a necessary precaution, he presented me with a plastic apparatus and a $500 bill, with a stern warning to be even more careful. But I simply couldn’t be more careful without hooking myself up to a feeding tube.

To my dismay, the cumbersome caps fell out once more that summer, each chain of events more traumatic than the last. The final fall out occurred while visiting a friend in L.A., so I had to finish the last two days of my vacation toothless, putting a serious dent in the physical and emotional recovery I was working towards. Back in New York, I made an appointment with a new doctor who came highly recommended. The caps were not a good fit in the first place, she explained, and would continue causing me trouble unless we started anew. Contemplating the upcoming two-week process, I shuddered to add up the hours spent reclining in the dental chair clutching the armrests, as I was drugged up, ground down, and glued in, again and again.

My new teeth looked exactly like my natural ones in size, shape and hue and that alone was an improvement. As days passed and my teeth held tight I slowly began to regain confidence—and not just in my eating ability. I was trying desperately to get back to the person I had once been, pre-Shane: a single, strong, independent woman, reminding myself that while I liked having someone else make my coffee in the mornings, I was perfectly capable of doing it myself.

A year later, I began having the strangest feeling. It enveloped me when I least expected it, maybe on a sunny day, when I was walking Frankie. Or upon realizing old Sex in the City reruns could actually make me laugh again. Or when I found myself really enjoying the company of friends. Finally, I felt present in my own life again.

When one breaks an arm the bone becomes stronger, and in that sense I wasn’t just happy: I was happier. I wasn’t just content, I was more content. It occurred to me when I ran into Shane in the neighborhood one Sunday, and felt absolutely nothing. Actually, I felt something. I felt a sense of pride and resolution, when he gave me a haggard, crooked-toothed, gnarly yellow smile and I flashed him my perfect new pearly whites.