It’s 9 pm. I’m in St. Louis, sitting at a table with three nurses in an Irish pub called O’Malley’s. As I nurse my first Vodka tonic (by no means my last) of the night, I’m scanning the place for a guy who looks like his name could be Max. Max has The List. You sign up with Max. There are a couple of regular looking patrons and a bartender who has already assured me he’s not Max. It’s empty here. Every time the door opens, my breath catches. I’m wondering, am I even in the right place?

It’s the first Monday in May, 2011. Osama Bin Laden is dead. St. Louis is recovering from being slammed by a tornado ten days earlier. When we’d taxied in from landing at the airport on Sunday, we could see the windows of the airport still boarded up from the storm. It’s cold for St. Louis, hovering around 50 degrees and raining all day—for weeks, actually. I’m here for work, for a health care conference, surrounded by nurses and doctors talking about serious things. In the morning, while the light was still dim, I’d stumbled bleary-eyed into the grand ballroom of this hotel to lead my team through the first of three long, dry days of learning.

I’ve also come to St. Louis to grab a certain brass ring for myself. Tonight. For six weeks I’ve been preparing for this trip. The night we arrived in town, I’d quietly searched the Internet for this place or for some place like this, someplace my speed. O’Malley’s is starting to fill up with scruffy 20-somethings carrying notebooks. I’m definitely in the right place. As I get up for a drink and take a lap around the room, I see I’m easily 10-15 years older than nearly everyone here. The energy in the bar is getting more intense, but no one is gravitating toward any one dude yet. These kids with their notebooks seem to know. Max has not yet arrived on the scene with the list. It’s 10 pm.

A few minutes later, the door of the bar opens and the energy in the room shifts. This is him. Max. He waves to his friends and sets up across the room with a notepad and a pen. The notebook kids surge across the room to sign-up for the comedy open mic—the reason we’re all here. I feel for a second like I’m going to pass out; my head gets real swimmy. I pound the vodka in front of me and I’m warm and slightly less panicked. I get up and walk over to join the throng assembled in front of Max. I get my name in and I’m number nine on the list. The List. Number nine. I will be ninth to tell my jokes. Well okay then.

- - -

Rewind. 10 am: Shortly after the morning conference session begins, my cell phone buzzes. When I step outside of the hotel ballroom to take the call, I can see my breath. I huddle under an eave of the building to escape getting stabbed by needles of cold drizzle. The call is from my ex-husband. There’s a problem he needs me to help solve and I can’t do it b/c I’m in St. Louis. It gets ugly quickly. The whole conversation is exhausting and results in me screaming at him that I will call my dad and my dad will have him arrested—a threat upon which I have no intention of following through, but for some reason I think is important to make at the time. I put my head in my hands and cry in the rain before I go back into the conference. I feel crazy and backed against the wall. I have to step outside several more times to put this situation closer to right. In a lighter moment, I make the mistake of telling him I might do stand up for the first time later that night. He tells me the concept mortifies him. I’m crestfallen. I consider abandoning my comedy ambitions for the evening.

In the first afternoon breakout session from the larger conference, each of the participants is asked to go around the table and tell our story and—as usual—I bring the room to a screeching halt with mine. I realize in that moment, if I let the difficult reality of my history—or of my day-to-day life—derail my sense of humor, the terrorists (or in this case, the jerks) win. I decide to go through with the open mic no matter what shit show this day has in store for me. There’s always a brass ring. Sometimes it’s unattainable—like finding a cure for cancer or bailing a sinking ship of a marriage. And sometimes it’s just stepping on the stage and telling a fucking joke. The trip, for me is now about getting on stage at O’Malley’s Irish Pub and getting laughs.

- - -

As a small kid, I remember having a crush on Steve Martin (that never stopped, actually). In high school, I wooed boys with my exhaustive repertoire of cribbed stand-up comedy routines. In college, we made a ritual of saving our money and taking the train downtown to see Emo Phillips and Judy Tenuta. I don’t think it’s putting too fine a point on it to say that I had been grooming myself my whole life to get onstage and tell jokes. If not to build a career out of it, then to be able to understand from the inside how complex and interesting and punishing a pursuit comedy—ironically—is at its heart. I wanted know better that which I loved.

In truth, I wasn’t coming to comedy as a total outsider. And that may have hurt me more than helped. Austin, where I live, is a town densely packed with humorists of all stripes. One of my oldest and dearest friends—I call him the overlord—curates the granddaddy of our city’s many comedy festivals. I’d seen countless shows, been moved to tears, and met my idols through him. The flipside of that kind of access was feeling out of my element and exposed when it came to the idea of trying my hand at stand-up. I was afraid that my sense of my own viability as a performer had become inflated during the time I’d been preparing to come out of the comedy closet, watching so many talented people swimming in the pool. I wondered if perhaps I was sort of talentless. Not something I—or anyone—could know, though, without trying out my material and letting the audience decide.

Before I left for St. Louis, I contemplated entering a local stand-up contest in Austin. I had thus far played my desire to tell jokes on stage pretty close to the vest, and when I mentioned to the overlord I was thinking of competing, his reaction was first and foremost, protective. He recommended against it with a firmly furrowed brow. And though he’d helped me workshop jokes and been supportive of my humorous predilections, he wasn’t sure any of this was a good idea. Not sure I should do it at all. I wasn’t sure enough, myself, to argue otherwise. I decided, for this reason, I couldn’t start out in Austin. I would second-guess myself right out of ever trying. This is roughly how I ended up in the ladies room of a Landry’s seafood restaurant in St. Louis, MO staring at a pair of underwires from a bra on the floor of the bathroom stall and rewriting my jokes on the way to the show.

- - -

As the comedians on the list before me go up one by one and do their sets, I think about the overlord and the other people who—out of protectiveness, fear or just plain not getting it—have told me I should not do this. I wish I could pack this room with them, but the point of doing these jokes in St. Louis is that it’s not Austin. Because just in case I fall on my face, fuck if I’m going to fall on my face at home. I drink another two vodkas really fast. The guy before me does seven minutes about masturbating with two dicks. Kill me. During his set, two other people move their slots on the list so as not to follow him. When he’s done, I take the mic, breathe and step onstage…

“Ladies and gentlemen, I’m here to tell you: I have become my poor relations. You know the ones—the ones who are proud that they live in a triple-wide? Yeah, you know. This morning I threatened to call the cops on my ex for breaking down the door of my apartment after his spare tire was stolen off the front lawn of my ex-house. I was making a go of being classy for a while. But that’s over. Tonight, I ate at a Landry’s and was surprised to find a pair of underwires from a bra on the floor of the bathroom. I know right? In such a fancy place… you know who thinks Landry’s is a fancy place? Say it with me: Poor relations…

“The city where I live has been absolutely overrun by hipsters. But it’s gotten to the point where I’m not sure they notice they’ve lost the element of rebellion and are dressing like my dad in the 1960s—like, nicely tailored pants and cardigans and black-framed glasses? It’s like watching bored Buddy Holly eat trailer food and listen to DJ music…

“And so, I said to myself, either he thinks escorts are relationship coaches, or he thinks relationship coaches are escorts. But either way, he paid for the happy ending. Thanks everyone. You’ve been great. Goodnight…”

My set goes passably well. A few bobbles, a few laughs. Not perfect, but not at all a failure. Afterward, milling about outside the bar with the other comics, a girl quotes one of my jokes back to me—the one about the cardigan. Holy fuck. I text the overlord from the cab on the way home and tell him what I’ve done. He’s proud of me. I am so very proud of me too.