The sleeve of Ally Sheedy's black dress takes a quick swim through her bowl of carrot soup and I watch with detached amusement as the orange goo sticks to her cuff. Sheedy, who is using her hands to pick out the crouton floating in her bowl of soup is oblivious to the mess, and I'm too petrified to say anything about her dress.

Just minutes earlier, a reporter from the New York Observer complimented her on the unique dress, which has long, dramatic sleeves and a slit down the front to show a bit of cleavage. It's the kind of dress a hipster witch would wear to a Halloween party, only it's the middle of summer and a sweltering 90 degrees outside.

"I love this dress!" Sheedy squealed, reacting to the compliment. "It's so gothic." When she lands on the word "gothic," a flash of the role that made Sheedy famous shines through. For a brief second, Alison, the bologna tossing, pixy stick eating misfit from The Breakfast Club, is chattering away to the sportos and dweebies.

The year is 2000 and I'm 23 years old, working my very first day at a try out to be the editorial assistant to Rush and Malloy, the famous gossip columnist duo at the New York Daily News. In the cloying humidity, my palms are sweaty, my tie is rumpled and any confidence that I will be able wring nuggets of gossip from this year's edition of the Independent Feature Project Awards is waning fast. Just a year-and-a-half out of college, I'm in over my head.

This notion comes to me the second I arrive at the IFP Awards, hosted by Jason Alexander and held in a swank ballroom in Chelsea Piers, overlooking the Hudson River on New York City's west side. After rushing home to change into the only nice tie I owned, I stand paralyzed on the lip of the red carpet, the epileptic flashes of a dozen paparazzi glinting off my 50 yard stare. Unable to move, but blocking the path, Harry Belafonte gently nudges me aside and waves to Spike Lee, who just entered the ballroom.

"Excuse me, young man," says Belafonte, as he rushes past. "Spike!"

The encounter, all of six seconds long, sends me into an existential crisis where all of my deepest fears explode into full bloom. While this kind of work is everything I dreamed I'd end up doing in New York -- to see the celebrities, to live a life vastly different than the one my parents lived and my friends were destined for -- the reality of it all is much different.

You see, in the world of gossip journalism, your job is to find things that will set tongues wagging, but all those news instincts you've learned in journalism school are useless. If there's a fire, you lead with the dead, injured and damaged. If there's a press conference, you relate what is said. But if there's an awards show packed with C-list celebrities, what's the story? Why should anyone care?

In order to get gossip, you need to cobble it together. I had to talk to celebrities. They needed to say things. I needed those things to move beyond the banal and into hot type that will sell papers tomorrow morning, so I could impress the bosses and keep this job.

And so, I had to choke back the self-doubt that had plagued me throughout high school and college. That I wasn't cool enough to get in with the right crowds. That I had nothing original to offer in my writing. That no matter how hard I worked, vapid people who knew the right people would be able to breeze on through to the red velvet wonderland.

But my hard work had paid off, hadn't it? I knew enough of the right people to get this tryout with the Daily News. I had an invitation that would allow me to breeze on through to the red velvet wonderland, so with my deepest fears in my throat, I cross the threshold to find out if I had what it takes.

To calm the nerves, I hit up the bar, fighting through a crowd of people when I realize that I'm the only person in the room without a jacket on, except for the man in the corner in the rubber T-shirt and the model attached to his face. As I belly up to the table, a compassionate bartender takes my order for a whiskey and soda, then stifles a laugh as I ask him how much they cost.

"This event has been sponsored, sir," he says, softly so only I could hear him. "You don't have to pay. It's an open bar."

With drink in hand, I walk to the terrace overlooking the Hudson River in hopes that I can jump in without attracting the attention of Frank Whaley or Ethan Hawke, both of whom are smoking cigarettes near the railing.

Since Whaley is the lesser of the two stars, best known for his role of Brad in Pulp Fiction, and because I've been a fan of Whaley's since he starred in Career Opportunities, a lost John Hughes classic co-starring Jennifer Connelly, I approach him first.

"Hi. Frank! Frank! I, uh, well, today is my first day as a gossip columnist at the New York Daily News and I have no good questions to ask you but I wanted to say that I really love your movies especially Career Opportunities which really ruled and stuff and I have nothing to say to you so I think I better go unless you have some gossip that you want to tell me or have anything that you think would make good gossip," I say, in one breath while fumbling with a cigarette. "Can I have a light? My name is Eric."

"Oh, um, sure, Eric," said Whaley, fumbling in his pockets for a lighter while casting his eyes around the room for the rope ladder and the helicopter that will whisk him far, far away. "Here you go. I need to go someplace else now, okay? Good luck."

I suck on the cigarette and watch Whaley scamper back up the stairs towards the ballroom, looking back in my direction when he hit the doorway to make sure I wasn't following him. While I never talk to Whaley again, our horribly awkward encounter became a running joke for the rest of the night, as I bump into him in the men's bathroom, sit at the table directly facing his and block the path he takes to return to his seat.

Without pride to burden me down anymore, talking to celebrities becomes a bit easier. I move on to Ethan Hawke soon after, using the exact same rushed monologue that succeeded so famously with Whaley minutes earlier. Hawke smiles like parents do when children accidentally scream "fuck you" to the cashier at a supermarket. Equal parts mortified and amused.

"Uh, well, I don't really have any gossip for you. Good luck, though."

He didn't pat me on the head, but he might as well have.

At that moment I officially gave up and realized my fantasy of becoming an in-the-know gossip reporter was total shit. Not only did I hate the job I've been asked to perform, I didn't have the faintest idea of what to ask the people I was supposed to talk to. Dejected, beaten and somewhat relieved, I drag myself to Table 19, where a happy little placecard informs me that Ally Sheedy would be sitting next to me.

Well, if I'm going to go out like this, might as be with a member of The Breakfast Club. And there she is, Ally Sheedy, in a floor length black dress, with a smile that's seven acres wide and a presence that overwhelms the few reporters sitting around the table.

Instantly friendly, Sheedy loudly proclaims that she almost didn't find the table and boy this is such a scene and that she voted for Michelle Rodriguez to win the Breakthrough Award this year because that girl was absolutely amazing in Girlfight. Completely lost in my own thoughts, contemplating my blown opportunity, I load up on red wine, offer a small hello and then the soup comes.

After a long wait, wracked with nerves, but unable to stop myself, I inform Sheedy that her sleeve is covered in soup.

"Oh, ha. Right," said Sheedy, dabbing at the stain with my napkin. "Who are you? Is something wrong?"

Once again, I explain my cluelessness and decision to quit, unable to unearth any gossip at the IFP Awards, failing to corner either Frank Whaley or Ethan Hawke into a conversation and damn near losing it after Harry Belafonte asked me to move aside.

"Don't worry, honey. You're only as cool as you think you are," Sheedy says, polishing off her wine and running a biscuit around the edge of her now-clean bowl. "I'm sure you'll do great. You're talking to me aren't you?"

Perhaps it's the wine, or the fact Sheedy's stained sleeve gives us shared imperfections, but I begin to relax. She talks about how bad movies are and how she can't find a decent script. We talk about her lesbian mother and her child and her husband, David Lansbury, Angela's nephew. We smoke some of her American Spirit cigarettes on the back terrace, as she discusses her removal from the title role of "Hedwig and the Angry Itch." We are a pair of outcasts in a sea of celebrity.

Because I have to, I tell her how beloved The Breakfast Club was to my generation of kids, who have not only memorized lines, but used the stock characters as religious icons when navigating our own paths through high school. I mention my own junior high school crush on Sheedy, who actually blushes, then reaches over and kisses the back of my hand.

And then the gossip happens.

"I think Winona and Christina Ricci totally copied Alison in a couple of their movies," Ally says. "Especially Winona. Did you see her in Beetlejuice? She totally borrowed from Alison."

When the IFP Awards end, Sheedy jots down her home phone number on a piece of paper and tells me to call her if anyone ever gives me any trouble. Indebted to Sheedy for saving me from drowning in a pool of C-listers, I never told my bosses about her thoughts on Ricci or Ryder, firm in my decision that I am just not cut out to be a gossip columnist. My aching stomach is a testament to that.

Sheedy wishes me luck and kisses me goodbye on the cheek. And while my future in writing had never been more uncertain, my existential crisis was passing with every step back up the red carpet, past the velvet ropes towards my small, overpriced apartment.