Two Writers Drinking, Sitting Around, Talking About Stuff

by Will Leitch (Dewars)
and Bob Sassone (Cointreau)

From: Will Leitch
To: Bob Sassone
Tuesday, December 3, 2002
Subject: Two Writers Drinking

Bob-

OK. I’m not sure the conceit of this whole project, but it appears it has something to do with sitting at a computer with various distillations and consistencies of alcohol and writing presumed witticisms and off-kilter bon mots to you. This sounds fine to me. This, minus your involvement, sums up a typical Tuesday, though usually there are bejeweled harlots.

Of course, I’ve never met you, Bob, just as you have not met me, as far as I know. I don’t even know what you look like. I tried to get you to send me a picture of you once, but you sent me a baby picture, which is kind of sick, actually. I’ve read your writing, and you’ve read my incoherent strings of dangling participles — if you don’t stop scratching your dangling participles, they will become red and inflammed — so we know each other in that sense. But I find myself fearing I will write something that will offend you. So to make sure I don’t start us off believing some sort of principle that will cause you to fester and boil before exploding in a murderous rage, allow me to rid myself of any possible insults at the get-go. Please do keep in mind that I know nothing about you and am just wanting a clean slate.

You’re bald.
You’re fat.
You once laid down with a dog.
You were breast-fed until middle school.
You are currently sucking on a broom.
You have a coven of adopted children from Nambibia.
You wear a girdle but are still covered in poo.

OK, we’re covered. Now. I have a few topics.

Women. I’m wistful these days, Bob, and I’m not even drunk  yet. Shit, I’m still at work, man! Imagine how sappy I’ll be later, after a few vats of Dewar’s. This could be trouble. I’m starting to worry about this assignment. How did you talk me into this, anyway? Nevermind the woman question. I am not sure I can handle it.

Movies. We could talk about movies. I liked —

No.

I can’t.

I can only talk about women, and the ones I’ve lost, and where they went. And through my drinking, I shall find salvation and resolution. With your help. With or without the girdle.

I’m leaving work in about 15 minutes and have a 45-minute subway ride home. I’m currently reading American Psycho. Is it wrong that the main impression I’m taking from the book is that this guy gets laid way more than I do?

See you in an hour or so, Bob. A pleasant Tuesday to you, and I hope your holidays were/are/shall be well.

Best,
Will

***

From: Bob Sassone
To: Will Leitch
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

Will,

To answer your potential insults:

– Yes, but in a “male pattern baldness” sort of way,
unfortunately, not in a Patrick Stewart, shaved head, damn bald-is-sexy!
sort of way.
– I have not worked out in over a year. Not
even walking. But I have somehow lost 12 lbs in the past two months.
Living on soup and Diet Coke will do that.
– Her name was Princess, a collie/German shephard. It was 1978.
– 9th grade.

– If you can call Cointreau a “broom,” then yes, I’m sucking away. In a shot glass from Moose McGuilicuddy’s in Hawaii. Where a friend and mine once picked up two racist girls from Mississippi. We spent over $100 on them at Trader Vics, then brought them to Moose’s. My friend’s date started making out with some guy in the dark corner of the dance floor. We left and went to McDonald’s.
– Ethiopia.
– Not when I’m sitting down. It bunches up.

I worry about this little experiment too. What if we come across as completely lame? What if we run out of things to talk about? Of course, being the propreiter of this damn web site, I also have the technical things to worry about. Will we lose any of the correspondence? (I beg you to hit “save”often tonight). What if there’s a power failure? What if this new Red Sox GM is too young and inexperienced for the job? Sorry, that last one was just a general worry.

I plan on an elaborate saving technique: in addition to saving these e-mails in my Outlook, I’m going to e-mail them to Yahoo as well. Or should I say Yahoo!

Ah, American Psycho. Beckerman is reading that right now too. I haven’t read it yet, though I hear the movie is even better. Doesn’t it involve power tools and the 1980s or something? I hope that reading it doesn’t hamper your scribblings here (Beckerman wrote a “What Xmas Means To Me” essay for me just after finishing the book, and it ends with him as a 9 year old stabbing Santa in the neck with a pocket knife).

As for women, I’m getting to the point where the holidays, especially Christmas, can be a somewhat lonely time. Sure, there are family members and friends and egg nog and those glorious TV specials where Jimmy Stewart runs around in the snow (side note: why is Clearance called “AS2,” Angel Second Class? Shouldn’t it just be “AS,” since the S already stands for 2nd?), and Rudolph does that herky-jerky leg kick thing as he guides Santa through the air, but the female element has sorely been lacking in the past couple of years. I don’t ask for much. Just a little companionship. I’m sick of this whole “loner” bit. I’m not a bad guy. I’m not deformed. I’ll never wear a wife beater T shirt. Is there some secret I should know about, as I approach the magical age of 38? Should I be married? Should I “settle down?” Should I have the 401 k plan, the house, the kid like my friends do? Am I even living in the right area? And why does Christmas make me think of all this things when visions of sugar plums should be dancing in my head?

Don’t even get me started on Valentine’s Day.

I look forward to getting your response to this e-mail aftervyou subway trip home. 45 minutes on the subway? Wow. New York City is such a big place. Be careful on that trip. I hear there are things like
“wildings” in NYC. Wildings. I heard that once.

Bob

***

From: Will Leitch
To: Bob Sassone
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

Bob

I apologize for the delay. That was an absolutely miserable subway ride. The train was 20 minutes behind schedule and was packed. My roommates are in Japan right now, and they were telling me that there are people in Tokyo whose job it is to push people into the subway train. This is a career path I had never considered, and I like it. I could explore my fascination with violence and frotterism (I am fairly certain I spelled that wrong) simultaneously. The trip was made worse because some idiot brought his dog on board with him. Even worse, the schmuck was wearing sunglasses even though the train was lit up just fine. My anger inspired me to push him around a little. The guy was too
stupid to even notice who was doing it. This city is full of morons.

I have just poured myself a hard-earned glass of Dewar’s. I never drank bourbon or whiskey or Scotch or anything of that ilk until I moved to New York. Somehow, it struck me uncouth to pop Jello shots and little plastic bottles of Southern Comfort among the intelligensia. By the time I realized that most of my colleagues and cohorts not only were not members of the intelligensia, but, in fact, spent most of their May evenings trying to piss their name in the snow, it was too late. I was hooked. Mostly, I appreciate the first swig of Dewar’s. I love the way it warms the cockles of my heart, and like The Man said, there’s nothing like hot cockles.

Anyway. I’m here. Fret not.

You’re concerning me with this moaning single talk. I mean, do you have brothers and sisters? They don’t pull that shit where they start introducing you to random strangers to see if there’s any
“chemistry,” are they? Do you go on dates? You’re a talented guy. You’ve got Joe Bob Fricking Briggs writing for your site, for fuck’s sake! Tell me about your last date. It couldn’t have gone that bad.

I can only wish to be so fortunate as to be able to avoid dating. Ex-girlfriends continue to treat me like an iodine high colonic. A recent one, one of those that really hurt, called me the other day. I hadn’t spoken with her since we broke up about six months ago. She told me how her life was, and how she went on vacation for her birthday (presumably with a tall, blond Aryan weightlifter with pectorals the size of Clydesdales), and how happy she was. I responded with my best Marlee Matlin imitation. Just a bunch of grunts and clicking sounds. The call lasted seven minutes. And that may be in dog time.

I dunno. I’m stuck on this lack of a date thing you have. I mean, you lost 12 pounds! It’s difficult to lose 12 pounds without, well, without chopping someone’s arm off.

What’s the hurry to get married, Bob? Is that what you want? I think what concerns me most about getting married is that my inevitable failures will just be multiplied when they affect someone else. It’s one thing when I’m sitting in my boxer shorts masturbating to Ren and Stimpy reruns on a Wednesday night. It’s another all together when my wife is with some other dude in the next room. My paycheck may be miniscule, but at least I don’t have to buy diapers, or pacifiers, or anything else my wife might want in her dresser. It’s less stress being by myself. You know?

oh.christ.i.am.so.alone

Hey, was I not invited to be in the holiday PBJ issue? I don’t think I received an email about that. Do you not like me anymore? What about that summer in Boise? (By Boise, I mean “my pants.”)

Best,
Will

***

From: Bob Sassone
To: Will Leitch
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

Will,

The danger of being at home and waiting for someone to get home is that the bottle of liquid refreshment is already at hand. I’m on my 7th shot glass of Cointreau (mmm…orangy goodness – it sneaks up on you and before you know it you are enveloped and lighheaded). But you don’t gulp Cointreau. You sip it. So I’m pretty buzzed right now. In fact, the most buzzed I’ve been since New Year’s Eve ’99. Wow.

Jello shots are lame. No character at all. Though I understand the attaaction.

Did I tell you I’m thkning of moving to NYC? I am. Seriously. Probably in February. Your roommates are in Japan? Damn, this would havd been a fine time to crash on your couch and explore the city. And yes, I am fully aware that the Cointreau is beginning to take hold and the spelling errors are about to take over. I have to get out of here. Nothing is happening.

Beckerman has it goin on. He’s got a book deal, he’s young, he has the cute girlfriend, and he’s a better writer than most peope at such a young age.

I have 3 brothers and 3 sisters. All older than me (yes, I am the “baby”of the bunch). They’ve never introduced me to potential lifemates. Nor have nay of my friends. What does that say? All of my friends are stable, with solid jobs, 401 k plans, kids, houses, insurance, solid jobs, that sort of thing. While I sit here flailing away at the writing game.

My dating life is massively pitiful. Once in a great while. I went on a blind date recently, and I also just got the phone number of an actress who I’d love to get to know better. Though I don’t know if she’s a lesbian or not. Not that it matters at this point.

It’s not marriage that excites me, but the IDEA of what marriage is: your soulmate, the person who loves you no matter what, someone you’ve commiteed to. I miss that. It’s not thjat I sit here and
dream of “marriage.” I dream of being special to a special someone. Is that pathetic? I apologize.\

I think that NYC inspires people to do a lot of things that they did not think of doing previously. Drink Dewars. Get involved in porn that sort of thing.

Fuck, I am shitfaced. I want to leave. Get out of MA and out of Boston and try NYC.

I did not invite you to do the holiday PBJ because we were doing this thing here (booze chat?). I didn’t want to inundate you (sp?) with various projects for no money. I feel guilty about that.

Approcahing my 9th shot of Cointreau. Damn.

Best,

Bob

***

From: Will Leitch
To: Bob Sassone
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

Bob —

Jeez, man, you are getting drunk. We’re off and running! That’s the spirit! I’m still not sure what this Cointreau stuff is, but the impression is building that perhaps you should not shoot it. I’ll tell you what; I’ll try to catch up. Let’s check the liquor cabinet. (By”cabinet,” I mean “Shit I found behind the freezer.”) Hey, that’s tequila! There we go. Down the hatch … boo-yah. Hey, that tasted like chicken.

All right, Bob, I feel obliged to be the turd in the punch bowl here. I remember when New York City seemed the answer to all my inadequacies, my insecurities. New York was the place I would
be understood! New York was where I would find my people! And at first, man, it was glorious. I worked for a clueless dot-com that paid me a shitload of money to impersonate an employee. But then it all crashed, and I crashed. Do you realize I once took a bus back from my hometown in Illinois to New York City, with all my worldly possessions in various suitcases, with my last 60 dollars in the world? I mean, I was stuck in Greyhound hell for 27 hours, five buses, four crack addicts asking me for packs of cigarettes. It’s hard just to get here, and then the trouble’s just beginning.

This is how it works here. You bust your ass for 10 hours a day and then try to rouse yourself to create something — the reason you came here in the first place — when you come home and don’t even have enough energy to fire off a respectable gas emission. You end up forcing yourself to write half-assed prose just so you can not be full of self-hatred for not writing because you’re too tired. If you’re lucky, you’ll find a job that pays you enough to afford a shit apartment where you can hear the Asian couple humping on the Persian rug through the styrofoam wall. And then you fight further, telling yourself it’s worth it, it’s worth it, it has to be worth it.

I mean, Christ, Bob, you’re not in Cheyanne, Wyoming. You’re in Boston. Hardly a sleepy village. You’ve got a little set-up there, and even though it seems stifling and exhausting, that doesn’t necessarily mean it is. I mean, look at what PBJ has done already. I’ve had at least 15 people tell me they didn’t even know I’d kept writing my Loser column after Ironminds until they found PBJ. How’d they find it? Shit, I don’t know. You’re the P.T. Barnum of this establishment. The point is that they did. People are noticing, man. If there’s one thing I’ve learned from my time here, it’s that it can suck the life out of you sometimes. Remember, I took about four months off from my column just to get my shit together and relax. The myth of New York is true; it’s limitless opportunities and fascinating, gloriously bizarre people. But it’s also hard fucking work, every day, a long weary slog just to have the opportunity to try to do your real work, what you came here to do. I’m not saying don’t move here; I’m saying do it the right way. Get a job, get a place, get a feel for the terrain … then come out here. It’s the only way to do. Trust me here. I tried it the other way, and it took me a year just to figure out exactly which was my ass and which was the gaping hole in the ground I’d just crawled out of.

Besides, do you know what they do to Red Sox fans here?

It occurs to me I sound like a nagging aunt, by the way.

But we’re becoming too serious. Let’s drift back to happy, pleasant topics … like girls!

Here’s why I admire your quandary: You still believe, man. There are so few people who still believe, who still think there’s a special person out there, the one who will make their food taste better, the one who will shine the grass a gorgeous yellow, the one who will Make It All Worthwhile. You’ve still got that hope, man. That’s a great thing, and don’t let anybody make you think otherwise. I mean, I’m dating this girl now, and she’s funny and smart and sweet and grounded and I’m sure is secretly quite eager to grind her high heels into my testicles, laughing as she swipes my wallet and compares notes on my lack of sexual prowess with, oh, every fucking girl who’s ever talked to me. That’s not good. Where you are is good. Hold onto that, dude.

Shit, we’re getting serious again.

All right. Poop. Fart. Shit. Ca-ca.

Oh, and relax on Beckerman. He’ll get the shit kicked out of him soon enough. He’s good enough to overcome it, but don’t worry; the devil will have his way with him eventually, like the rest of us.

Now that Red Sox GM … he depresses me.

You should go on more dates, though. Have you tried personals? I’ve actually had friends of mine meet their eventual wives through the personals.

Oh, and don’t think I was going to let this pass: New Years Eve 1999? Bob! Come on, man! You wouldn’t survive a week in NYC with such paltry experience. I mean, that’s almost three years. I hadn’t even moved here yet. That’s insane, man. Come on; pick it up a notch.

Hey, does Ebert still write for this thing? You know he hates me, right?

Best,
Will

***

From: Bob Sassone
To: Will Leitch
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

A confession: I am not a big drinker. I mean, I suppose I *used* to be, but now I’m not. That’s why this Cointreau has hit me so hard. Cointreau: imagine a Sunkist orange, mixed with acidiic booze. So
nice and comforting and deceptive. Mmmm…yum. But please catch up. Whatever you have to drink, however fast you must drink it, sip and sip and sip and catch up. I’ll still be here.

It’s not that I feel that NYC is the cliched answer to everything creative. It’s just that I think it’s the answer to MY particular brand of restlessness. Boston is by no means the boonies, but it sucks it all the ways that NYC does not suck. Beisde3s, I’m a writer, and if I don’t at least live in NYC for some period of time, then I am not serious. Right?

Right.

Boston, in so many ways, is a big dead end. Unless you want to write for academia or health-oriented companies or just work somewhere 9 to 5 and write on the side. At least NYC has that energy, that atmosphere of SOMETHING possibly happening. And I don’t even live in Boston, but north of it. Not even close enough to ber called a “suburb.”

I’ve always had a comfort zone here, north of Boston, in the world of “The Perfect Storm” and cheap rents. But I long for more.

The personals: I have friends who swear by them. That they’ve met women and thinks are SO hunky-dory. Internet personals scare the hell out of me. Though nothing else is happening date-wise. I know 2 people who met their spouses through the Net peronsals.

My dream of PBJ was to have a little haven for writing that didn’t get notifced otherwise. Things are certainly cool in that regard. But I long for more. I don’t have a job to keep me here, or a girlfriend, or serious business opportuities or land or anything like that. NYC seems like as good a place as any to exist the way I’m existing now.

Why does Roger hate you?

I am soooooo buzzed right now.

***

From: Will Leitch
To: Bob Sassone
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

Bob —

I will tell you, it may take me a while to get where you are. I am a most accomplished drinker; it’s a skill well within my strike zone. But, to give it a shot, I’m off to do two more shots. I am
purposely trying to avoid anything orange. Does Pepto-Bismol count?

I might take issue with the notion that you must live in New York to be a writer — personally, I think it only requires fingers — but I do know that itch, all too well. I can only suggest making sure you have your ducks in a row before you make such a move … have something concrete to come to, like a job, and an apartment. I’ve seen plenty of dreamers end up as shit stains on the sidewalk when they moved here without either. Get those, and then start the fuck running.

I’m cursing too much. I don’t like that I curse. In life, I never curse. I say “sir” and “ma’am” and “pardon me.” For some reason, I’m 2 Too Crew in print.

The movie “A.I.” is on. Haley Joel Osment freaks the shit out of me in that movie.

What are you doing for the holidays, Bob? I must go back to Mattoon. Last Christmas, I was in New Jersey, with a girlfriend who would break up with me a week after New Years. My family has yet to forgive me the misstep. Since then, the girl has lost 20 pounds, has ripped abs and arms and is making about three times what I make. I would make an incredible stock analyst; just buy when I sell, sell when I buy, and put a lot of money in “the next guy will be better looking.” Remember those old “Highlights” magazines for kids, and that cartoon “Goofus and Gallant?” I was Goofus.

How did you get in touch with Joe Bob Briggs? You realize that guy was in Casino? That’s
just amazing. I miss his old show on Showtime. It was on Showtime, right? He was hysterical in those “Hey, Vern” commercials.

Here’s a question for general discussion: What’s the most embarrassing interaction with a woman you’ve ever had because you were drunk? One time, I told a woman at a bar that I was singer Donovan Leitch’s son, and that Ione Skye (whose original last name is “Leitch”) was my sister, and therefore, I was related to a Beastie Boy. Actually, I am slightly related to Ione Skye, which is just horrible when I see her nude in a movie because, let’s face it gang, she’s hot.

OK, I must be becoming slightly tipsy. The paragraphs are becoming shorter.

My beloved Illini play North Carolina on espn2 (remember when it was all lower case, and Keith Olbermann was wearing skinny ties hosting the “nightly news wrap?” Nobody remembers that) in about 15 minutes, so it is possible that I will return to you full of intense rage.

Best,
Will

***

From: Bob Sassone
To: Will Leitch
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

Will –

Something about just saying fuck it and leaving for NYC – that appeals to me. I think I’ve exhausted all the other options. A job or apartment all lined up? No, not really. But winging it has its own
appeal.

I don’t think you have to live in NYC to be writer – not at all. Though experiencing NYC as a writer – that’s something I can get behind, especally since I don’t have a steady job, steady girlfriend, etc, to hold me here. In a way, I long for that hardship, that dream, that “open-endness.” I’m not naive when it comes to NYC; I just need a change.

This Christmas I am staying in Gloucester. Did I tell you that’s where I am? Gloucester, MA, 45 min north of Boston, home of George Clooney and “The Perfect Storm.” Xmas dinner with my sister.

I just sent an e-mail to Joe Bob, and he was open to writing for PBJ. It’s amazing who you can
talk to with a well-placed, coherent e-mail. People are much more open and nicer than some people think. Keith Olbermann once sent me a nice e-mail. I miss his show on Fox Sports Net. The one where he had an office that looked like some 50s newspaper office.

It’s very cool that people are repsonding to PBJ. Now, how do I make money at it again?

My most embarrasing interaction with a woman? I’ll dispense with the usual “tougne-tied while speaking with a woman,” since it’s something that every guy faces. But I was making out with a woman in a car once, when I was about 19, and she jerked me off and I came in her hand, all over the place. She said to me “I belive this belongs to you,” and proceeded to wipe it on my stomach.

Ione Sky: I love “Say Anything.” What’s that speech? I don’t want to sell anyting, buy anything that’s sold, sold anything that’s bought….etc, etc. You’re right: she IS hot.

Bob

***

From: Will Leitch
To: Bob Sassone
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

Bob —

It is difficult to describe to you the repulsed fascination I just had with that 19-year-old story. Lord. “This belongs to you.” Heavens to Betsy! That’s a funny story, and don’t puss out on me by not
printing it when this actually runs.

I”m watching the ILlinois basketball game right now. It is so depressing; the Illini have a very young team, almost entirely freshmen, and I recognize, like, four players. There was a time in my life when I would have produced detailed scouting reports on all recruits months before they wore the Orange and Blue for the first time. The price I pay for living here, I guess.

How you hanging in over there? I will confess, I’m starting to wind down. I’ve been screaming at the TV for half an hour now. The Dewar’s makes me angry when it comes to sports.

Well, if you do come to New York, wait until baseball season, because I’ve never made it to Fenway and plan on doing so next summer. Of course, I say that every summer.

Another high school friend of mine got engaged over Thanksgiving. Down they go. An amusing note: My ex-fiancee graduated with me from the University of Illinois College of Communications in 1993. Everyone in our major knew we were engaged, and put us in the alumni directory as husband and wife. This means that I’m now receiving requests for donations not only to William F. Leitch, but also Jessica N. Leitch. I’m deeply tempted to have a wing of the journalism building dedicated in her name. That might be funny. Right?

Not creepy. Right?

Best,
Will

***

From: Bob Sassone
To: Will Leitch
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

Will,

Yes, all of this will be printed. Whether it embarresses or not. How will we feel in the morning?

Yes, I am winding down too. 10:18pm. Does that make me a pussy. I fear it does.

My NYC trip is either going to be in February, or a summer expedition, May-July-August. We will see.

I haven’t been watching any sports during all of this. Just “The Guardian” and “Judging Amy.” How lame is that?

But Fenway is on me, when you do come here and visit. If you come in May or June, the Sox will be in the pennant race. Any date later than that, I can’t guarantee any baseball excitement.

When I was 16, my girlfriend Amy used to introduce me as her “hubby,” so I can understand the whole “Mr and Mrs. Leitch” thing. But that doesn’t mean it shouldn’t creep you out.

I have two non-married friends left. I don’t want to be the last, though at the same time don’t want to rush into anything.

You have the last word in this first round. Any comments? I am buzzed beyond recognition. Cointreau is meant to be sipped, not chugged.

Bob

***

From: Will Leitch
To: Bob Sassone
Tuesday, December 3, 2002
Subject: Re: Two Writers Drinking

It bothers me that I’m having a conversation with someone who watches “Judging Amy.” Christ, man. There are SPORTS ON! Were you raised by Segfried and Roy?

Yeah, I’m about done for the night. The cats are starting to wonder why I keep urinating on the carpet. Let’s do this again sometime. And Bob, please … next time, sip.

Best,
Will

——————–

Will Leitch’s “Life as a Loser” column runs weekly on The Simon. He has written for Salon, The New York Times on the Web, New York Press, Nerve, Ironminds, Playboy.com, and The Sporting
News.

Bob Sassone once beat Helen Hayes in an international arm wrestling tournament.

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