They just stared, their eyes wide and glassy. While they all had the same blank faces that looked, unblinkingly, at the tourists, each one had its own creepy variation.

Bart Simpson, for instance, looked like he had taken a few too many Xanax. Smurfette looked dim and slightly disturbed, like Papa Smurf had dropped her on her head as a baby. And Cowboy Woody, well, ironically his wide smile gave him an oddly perverse, horny grin as if he was watching Bo Peep undress through binoculars.

Those without giant plastic heads didn’t fare much better. Spiderman’s suit was ill-fitting and stained with what seemed like a decade’s worth of grime. I know firsthand that journalism is a tough and bad-paying profession, especially if one is in the quickly dying role that is the staff photographer of an urban daily, but from the looks of it Spidie’s gig at the Bugle wasn’t even paying enough for a trip to the laundromat. I would give the worst costume award to the guy I like to think of as Blackman — A tall African American man with no costume other than the trademark Batman mask and cape — if it weren’t for Elmo who was too tall and muscle-bound under the suit and had a matted coat that suggested a strange, feral quality to the famous red-furred toddler, as if the Sesame Street he was from was seedy and overrun by crack dealers.

We watched them, my friend Molly and I, from a metal table, painted nail polish red, right in the heart of Times Square. It was nearly nine o’clock on the night of my 23rd birthday. And there we were, sober and aimless, with nothing better to do than sit in the heavy mid-June air and watch a group of ragtag street performers parade around for tourists with loose wallets and low expectations. It had all the makings of some surreal play — big characters, theatrics, layer upon layer of cheap disguises and, of course, comical situations that could quickly turn tragic — sort of “Cats” by way of Beckett. And, In fact, it was a Broadway musical that brought me to the city, although a real one with a stage and lighting and performers not asking for tips through dirt-smudged masks.

Everything had seemed perfect that morning, before The Bad Thing happened, before we knew the way our night would end. I went into the city and, after stopping at a famous camera store known for its Hasidic Jewish ownership, I went to meet my friend Molly for dinner and then see the aforementioned Broadway musical, a present from her and her family from last year’s birthday. Busy and mismatched schedules meant that a year later to the day, I was receiving my 22nd birthday present on my 23rd.

I have known Molly practically all my life. We meet when we were both in nursery school. Although we were born the same year, when we first met I was four. She was five. I always liked older women. We stuck together through nursery school. We stuck together when she went to first grade in the public school system while I became a homeschooler. We stuck together through Hebrew school where I generally sat with the girls, who, other than Molly and another friend, were annoying and catty. One always complained she got migraines because she pulled her hair too tight in a bun. They were the prepubescent, chedar version of The Plastics.

Although many of the girls in my class weren’t great, the boys were worse — immature and disruptive, making stupid jokes and even leaving one teacher in tears. I don’t remember why these boys made our teacher Ms. D cry, although I think they might have been teasing her about a potential boyfriend. I don’t really remember anything about her other than she was young and sweet and not a terribly good teacher. While I felt bad that my fellow students were bullying this innocent woman who had the arduous task of teaching the sh’ma and the v’ahavta to a bored group of preteen Jews, I always viewed Ms. D as vapid and weak. She was a teacher and part of her job was standing up to unruly students and making the lesson plans interesting, if not entertaining, neither of which she did with any competency. Even if she couldn’t do that, at least not losing her cool when being teased by boys who are still a few years away from facial hair is a pretty good job qualification.

Looking back, though, I see it a bit differently. Sure, those boys were being assholes in that troublemaking, adolescent way, but the part I missed back then was that our teacher was probably somewhere between a high school and college diploma. Whatever led her to teach grade school religious classes is beyond me, but she was surely green and fragile. What I mistook at a young age for stupidity and bad teaching I can now see clearly and recognize the signs of a freshman educator in way over her head, gasping for air while an entire class kept pushing her back under the water. With no experience behind her and a group of taunting Jewfro-ed ghouls in front of her, of course she would crack.

It’s strange because at the time of our Times Square meeting Molly was about a year into a two-year assignment of teaching in a New York City public middle school. The kids she taught were no more than a few years older or younger than the boys who brought our Hebrew school instructor to tears, and Ms. D was, as far as I can gather, surely younger than Molly was then. While I’m confident that my friend was a better teacher than ours, I wonder if her kids look at her the same way I remember looking at Ms. D; like she is some kind of veteran teacher who’s expected to know the answers — how to deal with that kid that won’t shut up in the middle of a math lesson, how to pull apart a fight and how to get, and keep, the class’s respect. Molly recently told me that many of her students asked if she was married and had kids. Another guessed that she was in her 40s. Only one, a girl if I remember right, saw through it all and told her during a fieldtrip, “I know how old you are; you’re just a kid!” The words were clearly being parroted back from what her mother had said after a recent parent-teacher meeting, but still the words must have stung in only that way the bitter truth does.

As good of a teacher as Molly might have been, wasn’t she just a kid, flying by the seat of her pants in front of students who, although technically closer in age to Molly than she is to 40th birthday, viewed her no differently than the veteran schoolmarm down the hall? Who was she to try to act as teacher when just a calendar year before she was handing in homework rather than assigning it? Molly is a wonderfully kind, capable person any student would be lucky to have but at the end of the day I can’t help but wonder if my friend feels like she’s playing an elaborate game of dress-up, a perfectly enacted `let’s play school’ where no one remembers the rules.

Oh, but there’s the rub. You graduate college with a degree in history or English or business but do four years of marketing classes help when you get a job at a large firm? Will a teaching degree give you success when situated in front of thirty impatient kids? Besides, if college is indeed a stepping-stone between childhood and adulthood shouldn’t How To Negotiate Salary or How To Deal With The Shifting Relationship Between Employer and Employee be more important than Intro To Algebra? Learning how to deal with mean bosses and responsibilities and 401(k)’s, classes on how to sublet an apartment and what to do you if you think your post-graduate partying is out of hand? I can tell you that I’ve read some Great American Novels, memorized stages of the Kreb cycle, learned how to execute T and Z tests, wrote essays on the Iraq War, William Carlos Williams, the mise-en-scene in “Taxi Driver,” the role of mass media in the 1960 and 2008 presidential elections, William & Masters’ stages of orgasm, and the history of The Simpsons, but in that mysterious place called the real world do these things add up to anything besides being a wiz at Trivial Pursuit?

It’s like an experience I had in my second year of college when I had to have two pins put in my arm after breaking it in a painful if not banal accident. I was waking up from the anesthesia in my hospital room when I noticed that most of the nurses buzzing in and out of my room, checking in and futzing with the O2 Stat monitor on my pinky, were young, blonde and rather attractive girls. At first glance, that’s a pretty good revelation to make, especially when bedbound with a steady stream of narcotics coursing through your veins. It wasn’t even a normal IV drip but a miraculous concept known as Intravenous Patient Controlled Analgesia. It’s basically a DIY form of IV painkillers that gives you a shot of body-numbing medication every time you press a button located on a small, handheld device that looks suspiciously like the buzzers used on “Jeopardy.” Except with these, every answer is correct and your reward, although not monetary, is immediate and wonderfully pleasurable.

Hey, I may have been used as a human pincushion, one might think, but at least I have a Vicodin drip and a bevy of cute blondes parading in and out of my room, interested in every little detail of my life.

But, unfortunately, the details they were interested in were less about my rapier wit or academic achievements and more about my bodily fluids — and not even the fun kind. Besides, because of the location of the hospital I was staying, I often found myself dealing with nurses or aids who were either students or recent grads of the university I attended to and, while I’d generally love to talk about the construction in the cafeteria with an attractive classmate, the ideal time isn’t while the classmate in question is helping the other hobble to, and then try to unsuccessfully use, the toilet for the third time that day.

Speaking of that. “So, did you poop yet?” they would frequently ask while administering the supermodel special of round-the-clock oxycodone and laxatives. The joy buzzer of narcotics had a downside after all and due to pressing the button more times than Ken Jennings on a hot streak, I wound up unable to move my bowels for days. It had affected my bladder too and it wasn’t until a kindly doctor showed me a thin, plastic tube that he was to insert directed into my penis in an ungodly exercise not unlike snaking a backed up bathroom sink, that my terrified bladder decided to give up its well-fought battle and evacuate itself without the aid of the catheter. It was truly the number one number one of my entire life.

The reason I tell this story is because of something that happened near the end of my hospital stay. One morning, I was visited by a nurse who asked me how to turn on the heart monitor and why my arm was so cold, totally ignoring the ice pack defrosting on my bedside table. She was only a few years older than me and clearly new to the hospital floor so I should have had more patience with her, but I was drugged up, moderately constipated and recently threatened with the insertion of a foreign object directly into my genitalia, so my state of mind was not at its sunniest. I motioned to the sweating ice pack and told her I had no idea how any of the machines work, adding that they don’t tend to teach that in journalism school although, unless I’m mistaken, they might cover that information in nursing classes. Who knew snark was a side effect of a Vicodin drip?

I was at that age where the rusty cogs in the clock of life start to shift. The concept of the authority figure — the nurse, the professor, the rabbi — shifting from that of an omniscient figurehead to a contemporary, a person who didn’t inherently contain any more skills or knowledge or guidance than I did. Besides maybe a police officer or judge, the idea that the power structure has switched and, due to the caste system being overturned, you and our age-mates are no longer solely on the bottom rung, is up there with “You are no longer eligible for your parents’ insurance plan” and “It feels good when I touch there!” in terms of startling self-discoveries.

One moment you and your friend are fighting over Playmobile pieces and the next you hear he’s an airline pilot. You meet a girl in summer camp who makes up her own cat language and, in what seems like the blink of an eye, she’s a mother and high school music teacher. One moment you’re a drug-addled, uncharacteristically impatient patient lying in a hospital bed, showing off your ballooning hand to a naïve nurse and the next minute you are that nurse, getting berated for a lack of knowledge that’s no fault of your own. One moment you and your friend laugh about that one awful, unprepared teacher you both once had and the next your friend is that teacher with a classroom of judgmental eyes starring up at her.

A lot of my uncertainty had to do with the fact that I had just graduated from college and this was the first time Molly and I met since my diploma had become official. Although we are roughly the same age, I had transferred schools, which lead to graduating a full year later than most of my age-mates. For the first 14 years of our relationship, we had always talked as one student to another, but then in the spring of 2012 it became a dialogue between a student and a teacher. Nothing changed on the surface but below there was an underlying, rumbling seismic shift as she left the world of the student and joined the world of the adult. She had moved to New York, started a life and begun teaching. I stayed in my home state and threw myself into my extra senior year with a thankful abandon. But then that too ended, as fast as time goes when all you want it to do is slow down.

My graduation was a soggy, rainy affair that happened on the large quad at my school. By the end of the entire ceremony, I sat huddled and shaking with a friendly, big-bosomed girl who is now a local news anchor, our teeth chattering and our four-cornered, black hats melting like soggy grilled cheese sandwiches on top of our heads. In that moment, I was oddly numb. Yes, I was happy to be getting a diploma and proud of the work I had done over the past five years. Yes, I was thrilled to be sitting there with my classmates, come, quite literally, hell or high water, celebrating what we had accomplished together. And yes, I was worried, like every single one of the 500 or so graduates dripping wet on that quad, where exactly my life was headed. But at that moment all I could focus on was figuring out where I had to stand and how not to fall down the slippery stone steps.

It wasn’t until later, long after I’d dried out and the real diploma came in the mail, did I begin to thaw and realize exactly what that piece of paper meant.

In the fall, I had nowhere to be.

For the first time in my entire existence, the course of my life wasn’t planned out. There were no more prerequisites, no assignments, no requirements. The things that have given me my greatest stresses and greatest accomplishments — my GPA, that grade I got on a difficult Stats exam, when the next break is, the drama in the editorial department of my school newspaper, the classes I got into and the ones I didn’t — mean virtually nothing. I knew I was graduating with honors and a strong undergraduate resume. But I also knew that Ms. D got her Hebrew School job over other willing, qualified applicants and that that poor girl with a blind spot for medical equipment probably gradated college with a killer resume, both having the applaudable but misguided confidence to chase their dreams.

I told Molly all of this over dinner. About my sodden graduation and lack of post-college plans, the job applications I started to send out and the lack of responses I had gotten. These things took time, I told myself, and the job market is at an all-time low. Who was I to complain about my lack of responses with the ink still wet on my diploma? But I couldn’t lie and say a part of me wasn’t dismayed by every rejection, every cover letter that went unanswered, every friend of mine who quickly landed a job straight out of senior year. They taunted me with the qualifications and experiences I seemed to lack and made me feel like I was standing on ground as slick and uneven as the wet stairs leading up to the graduation podium.

After I complained about my future and Molly complained about her present, we slipped back into our shared past and had an incredibly enjoyable dinner. I am an only child and Molly, whom I have known longer than any other friend, is perhaps as close to a sister as I’ll ever have. I had missed her since she moved away and seeing her was just what I needed to curb my post-college slump.

But then that Bad Thing happened, the one that ended up with us engaging with a half dozen cartoon characters on the dirty street of Manhattan.

I guess now is as good as any to get to what The Bad Thing was. I dare not go into a large amount of detail. The guilty party has been through enough and rehashing the specifics in such a public forum will do nothing more then pick at old scabs. But here are the general details. At dinner, about two hours before seeing this Broadway play, which was a present from Molly for my last birthday, we decided to look at our tickets to see what seats we had. Upon inspection, we quickly realized that our tickets were for the Sunday three o’clock matinee not the Sunday night 7:30 show we were planning for. A certain member of one of our families had written the wrong time in the calendar and was so convinced of the time he/she had not double-checked the day before. As it turns out, Broadway plays don’t even generally have a Sunday night show but before we knew that, our gregarious dinner table turned into a tense War Room strategic meeting about how our night would progress. There were no shows to exchange our tickets for and complicating the fact was that my birthday happened to fall on Father’s Day so many other usual venues were shut down. No comedy shows or no live music to go to and I’m nearly Amish in my dislike of bars or loud clubs so there was nothing to fill our night, at least in the Times Square area where we wanted to stay given the location of my hotel room.

While I hate to admit it now, I was angrier then I’d been in a long time about my carefully laid-out birthday plans, despite the best intentions, ending up as a four-car pile-up of a celebration. It was a stupid mistake. A stupid mistake simply out of my control. Out of my control like the date and the fact that, despite a city teeming with life and opportunities we couldn’t come up with a single viable option other than watching tourists take photos with a leggy, Puerto Rican Wonder Woman. So were the resumes that slipped out of my hand and into a black hole of mailboxes and unknown desks and the chance that anyone would see me as anything more than one of the thousands of faceless graduates that come through their inbox. I chose to walk across that stage and I chose to put out my hand and I chose to pick up that diploma but since then, in a summer of uncertainty, those actions and the stability and regularity of the life they represented felt like a million miles away.

If I couldn’t figure out a show time, figure out something to do in this bustling city, who’s to say that I’d be any better at figuring out the bigger things when I got home? Would I be able to seamlessly morph from student to professional, from follower to leader? Would I be able to convince anyone, let alone myself, that I was something more than a kid wearing his father’s borrowed tie and jacket? I trusted I would follow in Molly’s footsteps, who, despite some unavoidable growing pains, was able to integrate herself into the role of authority figure in the eyes of kids whose understanding of the adult word is still vague and drawn in large crayon strokes. But sometimes late at night or lost in a sea of third-rate mascots, I wondered if my transition would be more hopelessly close to Ms. D’s or that nurse’s, ones that probably started with optimism but ended in a harsh reality check. Would that transition be as muddy and ill-conceived as my first post-college birthday, with my future employers seeing through my rouse, like the life-size cartoons I was watching, as if I too were a piss-poor facsimile of the character I’m meant to be?