Nice Try

by Josh Gondelman

  Still, I took the opportunity to engage in another venerated college tradition for the first time: drunk texting. I fired off messages to as many childhood friends as I could think of, most of whom were impressed that I’d gotten wasted (or at least . . . disheveled) but disappointed I’d done it without them. I stayed up late into the night exchanging giddy texts with old friends, partly because of the endorphin rush and partly because I had a Motorola flip phone at the time, so texting took longer than it does now. Once again, not to sound old, but: kids today with their predictive text have no idea the hell we went through in the early aughts! There was a time where to type an uppercase C you had to hit the 2 key half a dozen times! Show some respect, whippersnappers!

  Regardless of whether my goodwill was psychosomatic, I loved the sensation of free-flowing enthusiasm, and I hated how much I loved it. I was the sober friend, the sensible one. Once the novelty of “Josh is drunk for the first/second/third time” wore off, drinking would just be something I did. I’d be simply another person who went out and had fun, just like everyone else. What a nightmare that would be. Even at peak inebriation, I didn’t say or do anything ridiculous; I mostly told everyone I’d ever met that I loved them, which I probably did only because that’s what people do in the movies after several beers with friends. And they, generously, allowed me to puke feelings into the cars of their lives.

  I still drank infrequently for years after that. As long as I lived in Boston, I kept driving my friends around, unwilling to give up full control of my nights but a little looser with my command over my faculties, especially in safe circumstances. I’d have a couple of beverages at a wedding or maybe one at a party we were throwing wherever I was living at the time, as long as I could be mathematically certain I’d be sober when it was time to leave.

  When I was twenty-six, I moved to Manhattan, where no one drives, so no one ever asked for a ride. The public transit runs all night, and taxis cluster along the most populous streets like swarms of bees. Sometimes I have three or four drinks, just for fun, and out of courtesy to the city’s cab drivers and train conductors, I’ve never thrown up before I arrive at home.

  Have Fun

  “Have fun,” my friend Myq Kaplan1 used to say when it was my turn to perform at the open mic at Dick Doherty’s Beantown Comedy Vault, which remains, a decade and a half later, the comedy club with the most cumbersome name I’ve ever heard. It was good advice, and like most good advice, it seemed hard to put into practice, so I didn’t.

  I was nineteen years old and brand new to stand-up. Myq was a few years older and was already a working comic, which was the only goal in comedy I felt comfortable aspiring to. I’d never met anyone who had a stand-up special or wrote for a sitcom. But Myq got paid to tell jokes, which seemed both exciting and eventually possible for me, too. He emceed at the clubs around Boston and, in fact, performed basically anywhere in New England with a stage: Elks lodges, folk music venues, Chinese restaurants. Myq’s act was heavy on rapid-fire wordplay, and the smart, dense jokes stood out at open mics, where a substantial portion of the entertainment sounded like the introductory speeches at a support group for young men who are addicted to masturbating.

  I always appreciated Myq’s advice; it was nice to have someone be nice to me. Not that the other comedians were cruel. Most of them barely paid attention to me. I eventually made friends with some of the newer comics, but at first we were all too wrapped up in our own neuroses to engage with one another. We buried our heads in our notebooks backstage, slyly watching each other’s sets, but not confident enough to compliment each other on a job well done for fear of seeming uncool, or worse, overeager.

  The more established comics, stopping by to try out a few minutes of new jokes, didn’t seem to notice us at all. Before and after their sets they hung out at the back of the bar upstairs from the basement showroom, talking among themselves and drinking bottles of Michelob Ultra for some reason.

  I would have welcomed any attention, even the negative kind. A little trash talk would really have put me at ease. Not a withering critique, just the kind of shit you talk to your friends’ faces because they know you don’t really mean it. It’s much better than being bad-mouthed behind your back (although that can still happen in these cases, too) or being ignored entirely.

  There’s an apocryphal Boston comedy story I’ve heard for years in which a headliner goes up to his opening act and says, “Look, man. I’ll give you twenty bucks if you go out there and just eat it for the whole fifteen minutes. Crickets. No laughs. A total bomb.” The opener rolls his eyes and goes out, where he has a fine set to a decent audience response. After fifteen minutes he gets offstage to see the headliner, mouth agape, twenty-dollar bill in hand. “I didn’t think you’d really do it,” he says, palming the bill to the opener.

  I wanted that so bad, the whimsical cruelty of “we all belong here.”

  Years later, I was backstage waiting to perform my first stand-up set on national television on Conan. I chatted with friends and picked at a veggie plate. I was pacing the greenroom, propelled by nervous energy, when Conan O’Brien (the titular Conan) came through the doorway.

  “It’s so nice to meet you,” I said. “Thanks for having me on your show.”

  “Well, that’s not a done deal yet,” he said, his face stern. I laughed. It was the most comforting thing I could have heard. For Conan to come backstage and make fun of me right away sent a clear message: “I think you can hang.”

  Still, absent that, I remained grateful for Myq’s consistent kindness and unwavering advice. It was never “have a great set” or even its superstitious backstage surrogate, “break a leg.” Every time I was about to take the stage he’d say, “Are you up next? Have fun!” That was my comedy North Star, the effort to enjoy myself. And the fact that someone had taken the time to give me any kind of sincere feedback was almost as good as being made fun of. Without Myq’s input, I don’t know if I ever would have gotten comfortable.

  But for my first year doing stand-up, I was unable to take his simple direction. When I was onstage, having fun never entered my mind.2 If Myq hadn’t mentioned it, I wouldn’t have even considered the idea of fun. I didn’t get into comedy because it was fun. I did it because it was exciting.

  I first performed at the Vault the summer between my freshman and sophomore years at college. It was an easy commute, only a twentyish-minute drive from my parents’ house. But when I got back to school in the fall, the trip became much more difficult. First, I had to remember to call the club booker on Tuesday to secure a spot the following Sunday. Then, that Sunday at seven I’d hop on the free shuttle bus that the Brandeis administration ran over the weekend so the student body didn’t get stir crazy and turn the campus into the hotel from The Shining. I got off the bus in Harvard Square and took the subway the rest of the way downtown.

  I also had to drag two paid audience members with me in order to secure my spot onstage. It’s what’s called a “bringer show,” which is a club’s way of wringing a cover charge out of audience members who are about to see a show that’s not really worth paying for. Usually I brought friends from Brandeis. When I couldn’t entice any of my classmates into the city, I’d desperately try to con friends who went to college downtown to come to the show. On a few especially dire nights, I begged my dad and sister to drive into the city and cough up the seven-dollar entry fee.

  Most weeks, as soon as my set ended I collected my things (notebook, pen, iPod) and ran out the door to catch the last free shuttle bus back to campus. This wasn’t a paid gig, so I was already losing money on the night. And if I had to take the commuter rail back from Cambridge to Waltham, it doubled the amount of cash I’d have to spend on travel.

  And while all that was a thrill, it wasn’t exactly fun. It was new and interesting and stressful and satisfying. But it wasn’t really a good time. As much as I enjoyed learning a new skill, I hated that I couldn’t get better faster, and the times onstage when the laughs wouldn
’t come felt acutely unpleasant.

  I had to find the excitement in the little things because, on its face, the open mic scene in Boston in the early aughts was not exactly glamorous. Though there were other shows around the city, I mostly stuck to the Vault, a seventy-seat club in the theater district, named because it was housed in the basement of an old bank. The greenroom was behind the literal vault’s circular doorway. A twelve-inch-thick reinforced steel door sat perpetually open in the showroom, held ajar by the table farthest from the stage. The weirdness of the room was offset by the smothering normalcy of Remington’s, the bar upstairs that the club rented space from.

  Remington’s was the kind of place where you could guess the entire menu before you saw it. In fact, the bar itself had the same cozy level of “don’t think too hard about what’s in this” as a loaded potato skin. And they had Stella Artois on tap, but someone would undoubtedly make fun of your fancy European airs if you ordered one. It was kind of like Cheers, but (ironically, considering the business downstairs) the patrons were less funny. By the time the open mic started on Sundays at nine, it was never that crowded.

  For months I was too nervous to speak above a squeaky whisper onstage. Even now the energy of my stand-up act is only as electric as what you might generate by rubbing an inflated balloon against a carpet. Back then it was practically a short circuit. The comedy part of comedy was a science experiment for me back then. Can I make the crowd laugh at a thing I thought of? And if so, could I make another crowd laugh at it the next week? If an experiment isn’t replicable, after all, it isn’t valid.

  The excitement in my first year of comedy didn’t come from anything going particularly well. It came from the knowledge of how badly things could go on any given night. The quality of an open mic has a claustrophobically low ceiling and an ear-poppingly low floor. And when you’re starting out in comedy, performing is a lot like skydiving,3 in that the best-case scenario is that you avoid the worst possible outcome, and you walk away living life exactly as you did before.

  And given the amount of legwork it took just to get onstage, a bad set felt extra bad. After all, there’s nothing like bombing in front of your family after conning them into leaving the house on a Sunday night to make them say, “Don’t you have homework you could be doing?”

  After several months, though, the shows began to feel more routine. The other comics’ faces were more familiar, my own nerves less pronounced. I was getting better, for sure. But I was in an uncanny valley where I had gotten consistent enough that I didn’t feel energized by the possibility of failure, but I didn’t know how else to enjoy myself. On nights when the excitement wasn’t there, I’d manufacture it. I paced before my set. I played loud music in my headphones backstage to try to coax out the adrenaline. Sometimes it worked, and other times it didn’t. But I didn’t realize I’d strayed off course. I’d been ignoring the only real advice I’d ever received. Have fun.

  My reminder came from an unlikely source. Tom, who is now a good friend of mine, was one of the most intimidating working comedians at the Vault. He was skinny and smoked cigarettes in front of the club and had a cutting sense of humor. If you passed him as you came offstage he’d often tell you, “Good set” and then, after a pause, “Eh. I didn’t watch.” It wouldn’t have felt so bad if he wasn’t so funny. His act was very dirty and very mean. He was still finding his voice, but when his jokes hit, they struck the audience like a sledgehammer.

  One night, I was sitting in the lowercase vault in the uppercase Vault going over some notes I’d written for myself. Tom came down the bar’s back stairs and walked over to me.

  “Are you a comic?” Tom asked. I sat up straight in the booth, proud to have been recognized as a small part of the humble tapestry of the local comedy scene.

  “Yeah!” I said, with disproportionate enthusiasm.

  “Then give me a pen,” he demanded.

  The back of my neck tingled with embarrassment. I’d walked right into his sucker punch. I handed over my pen, and Tom walked away with it. As he left, I smiled, realizing I had been recognized after all. Oh, right, I thought. This is supposed to be fun.

  The Blank Postcard

  Most people become less exciting as they age, retiring from parties and extreme sports. I have become slightly more fun as I’ve gotten older, but only incrementally, and the bar was set pretty low to start with.

  When I was twenty-five, I started a long-distance relationship with Leah, a younger woman who didn’t want to be anyone’s girlfriend at all. She was twenty-two, just out of college, and vibrating with ambition. Leah was small with big, wide eyes, which earned people’s trust, and a smart, vengeful brain that would destroy them if she felt they had underestimated her. She was a talented writer, and as soon as she’d finished school, she moved to Manhattan, where she worked in media like the protagonist of an HBO prestige comedy. I was still teaching preschool and doing stand-up around Boston, where we’d met.

  I visited Leah at her New York apartment that August, and that night she said both “I don’t see myself having a boyfriend right now” and “This doesn’t have to be a whole big thing, right?” Her explicit reluctance to be in a relationship was, in retrospect, the first sign that maybe we shouldn’t have been in a relationship. But despite the two hundred miles between us and Leah’s constant insistence that she was a wild stallion (or . . . mare?) who could not be tamed, things continued to get more serious. We texted every day. We spent hours on the phone. One of us visited the other at least twice a month. That’s only a casual relationship if you’re talking about your conjoined twin.

  By December, it was time for the ceremonial Meeting of the Friends. On account of the distance, Leah hadn’t had many opportunities to submit me before her friend group as Boyfriend Material. It was decided that on New Year’s Eve, I would visit her in New York, where I would tag along on a Girls’ Night Out. So the Girls’ Night Out signal was sent into the air (a group email chain), and I steeled myself for an evening of high-impact bonding with a Voltron of childhood friends, high school friends, college friends, high school friends’ best college friends, and college friends’ high school best friends.

  But as December 31 drew closer, the Girls’ Night Out gaggle began to dwindle. A last-minute trip out of town popped up here. A boyfriend surprised someone with restaurant reservations there. Somehow, New Year’s Eve had managed to become a disappointment before it even started, which even for New Year’s Eve must represent some sort of record.

  I did feel relieved to have avoided such a high-stakes night of socializing. But part of me worried that if I never became enmeshed with Leah’s larger social group, I was more likely to be dumped. Determined to create enough fun memories to keep the relationship moving forward, I suggested we get tickets to a show the Roots (my favorite live band) were playing in Brooklyn. The only tickets left were on Craigslist, which meant they could have been legit, counterfeit, or a trick to bring strangers close enough to murder them. Leah, the intrepid Manhattanite, met the seller in person, remaining mercifully unmurdered throughout the transaction.

  Our plans had, in my opinion, taken a turn for the better. Then Leah suggested a wrinkle to our evening, and her proposal consisted of the only New Year’s celebration more daunting than a Girls’ Night Out.

  “On New Year’s Eve, I think we should do molly together,” Leah said. At first I thought she had just issued me a casual invitation to participate in a threesome. Who is Molly? I thought. Is she your friend with the septum piercing? Is she already on board with this? Do I need to start working out? Of course, “molly” did not mean Leah’s college friend who had moved to Detroit to make house music while living in an unfurnished warehouse and who identified as “sexually omnivorous.” In fact, that’s not even a person who exists; I had invented her in a panic.

  In this case, “molly” referred to the street name for pure MDMA, the active ingredient in ecstasy. You have to hand it to drug dealers: they’re always innovatin
g. The problem with ecstasy, apparently, is that while in its pure form it’s an intense high and not especially addictive, it’s often cut with less expensive drugs like heroin or cocaine. To me, the fact that people used heroin to make a substance less potent was terrifying. “Let’s get a little of the stuff that killed John Belushi into the mix. Otherwise it might be too much for people,” was not a comforting sentiment to me.

  “How do we know that there won’t be any of that stuff in the molly?” I asked, naively.

  “Because then it wouldn’t be molly,” she explained, shaking her head. It seems like MDMA brings out the sommelier in any peddler of illicit pharmaceuticals. If the grapes aren’t from the Champagne region of France, you’re not drinking Champagne, and if there’s any crushed-up Adderall compounded into your little white tablets, you’re not really swallowing molly (and don’t let your local dealer tell you any different). “It’s a nice thing for couples to do,” she continued. “They used to use it for therapy. It’ll bring us closer together.”

  Getting closer as a couple sounded appealing, especially since we spent most of our time geographically (and emotionally) remote from one another. The idea of doing drugs, however, was somehow even more stressful to me than the concept of sleeping with two women at once. And yes, I encourage you to take a moment to verify and digest the fact that you have just read the most unfun sentence ever committed to paper. In terms of pure opposition to pleasure and joy, that arrangement of words is right up there with “The amusement park is closing early for routine maintenance!” It is a profoundly square stance to take, one that even Huey Lewis would not defend as hip, and the News would back him up.