I have this one tooth. It’s the lateral incisor on my right. It sits back behind my canine and my central incisor — a punishment for abandoning my retainer too soon. In the wrong light, I can look like a hockey player who lost a fight with a puck to my mouth. In the best light, I look like the kid whose teeth just grew in and whose parents still haven’t booked her appointment with the orthodontist.

I see it in every photo and every time I go to smile, I’m aware of it. But the tooth that make me look like a kindergartner doesn’t stop me from smiling. Life’s too short not to smile… but it does mean that I usually fight to stand on the left of any portrait (a fight I always inevitably loose.)

In the summer of 2012, an upper wisdom tooth abscessed, and before I could say “ouch” I was under anesthesia and undergoing a double tooth extraction. I woke up in a dentist office overlooking Central Park and stumbled a few blocks south east to the Brasserie, where I complimented some mild pain killers with a martini before passing out again at home. I was lucky — my face was barely puffy and when I went out the next day to celebrate the return of a few friends from the London Olympics, no one could tell I had just survived an oral surgery that seems to knock people off their feet for days.

The trouble came a year later when my teeth started to shift again. Jaw and tooth pain compounded with my misplaced incisor inspired me to look into the full orthodontic works. I could handle braces again, I thought. I mean, I already look like I’m 16, why not? It might be nice to be carded more often again.

When it turned out I was a candidate for invisialign, I was pretty stoked. I could handle having braces in my social life, but being ol’ metal mouth again in a professional one was less appealing. It was even better when my quote for the treatment came in under my no-go threshold.

So on December 28th, my dentist attached some pretty sexy anchors to my teeth and sent me home with my first trial.

It was like wearing a mouth guard. Within the first hour, I was kicking myself. My lower jaw was jutting out, I couldn’t figure out how to keep my mouth closed, and saliva was pouring down my chin in the most unattractive way. I lisped and talking for more than 30 seconds was exhausting. Was this sheer act of vanity destined to be my downfall? That $7,000 could have been put to good use elsewhere… like on clothes. Would lipo have been less expensive?

“There goes your sex life,” my mother said as she passed me a tissue.

It was family movie night, and as we sat in the theater watching the coming attractions, a large drop of drool fell out of the corner of my mouth and onto my shirt.

It was something I hadn’t considered. Between tooth brushes and birth control, there were already enough accessories to pack on an adult sleep over, adding an invisalign kit into the mix definitely exed the possibilities of a casual overnight. Plus, “honey, just excuse me while I put my teeth back in,” is not the sexiest phrase for the under octogenarian set.

Being ready for anything just got complicated.

My new life as a single girl with dental appliances was put to the test faster than I expected. In another display of my talent for Bad Timing, I had scheduled a first date with a dreamy commercial pilot turned lawyer within the first 24 hours of beginning invisialign.

For the most part, it all went off without a hitch, largely because I left the device at home. However, my teeth hurt so much I couldn’t chew anything more solid than mashed potatoes and everything we ordered seemed to be made of bricks. As our date moved into its 6 hour (and my third, maybe fourth? drink) I started getting anxious — I had passed my 4 hour invisialign-free limit. And I was hungry. Like, really hungry.

Our good night kiss was brief. Like Cinderella I had to get home before the clock struck “too late!” and my tooth shifted back into its crocked place. Orthodontics are at least as expensive and irreplaceable as glass slippers…