Two Writers Drinking, Sitting Around, Talking About Stuff – Part 5 (Special All-Wine Edition)

by Will Leitch and Bob Sassone

To: Will Leitch
From: Bob Sassone
Date: Tuesday, November 29, 2005

Hey Will,

I was looking through the archives tonight, and our last Two Writers Drinking was February 1. That’s almost a year ago! So much has happened in the past year. Paris Hilton got engaged to a guy named Paris and then unengaged. Paris and Nicole broke up. Now Paris and Nicole are getting back together for another show. Bo Bice hurt his foot *and* had a kid. They filmed not one but *two* films about Pope John Paul II. I bought a new pair of sneakers (New Balance). But most importantly, you have a book coming out! A book! Let’s talk about that.

By the way, I’m drinking wine tonight. Rodney Strong. A 2002 Cabernet Sauvignon.


Bob —

Hello. It has truly been a long time. The last time I talked to you, I was unable to grow facial hair. Now … well, let’s move on. Oh, and I’m pleased to see you have kept your finger on the pulse of American culture and history since we did this last. You TV bloggers. Honestly — and I know you’re not going to believe me here — there is a sun outside. It’s actually quite nice at times.

Yes, yes, the book. It is called Catch, and it’s released by Penguin’s Razorbill imprint. It’s funny, because I finished writing it a year ago and it’s just now coming out. I know this is par for the course with books — usually even longer, actually — but I’m so used to Internet time that I had to go back and read it last week to remind myself what it was about. I feel appropriately up to speed now.

Unfortunately, I’m not any better at giving a synopsis of the plot than I was when I wrote it.

So let’s try this: It’s about a kid from a small town, in the three months after he graduates from high school, before he goes to college. He meets an older girl and decides whether or not to leave his small town. That was horrible. I can’t write anything ad-copy like that doesn’t sound as if it were a third-grader’s reporter of how his Thanksgiving break went. I suppose, in some ways, that’s a good thing.
It has been a fun experience, I have to say, though, ultimately, the most fun part of a book is writing it. Not that I’m on some huge press tour or something, but I am consistently poor at talking about it. I will say, however, that my first foray into fiction was an eye opener. (And this is where MFAs groan, so, you know, get ready.) It’s very exciting to me — having written so much non-fiction — to be able to make the little people in my stories go where I want them to, rather than where they actually went in real life. This is going to sound dumb, but in a way, I found writing fiction more freeing, almost easier than writing non-fiction. I can make happen whatever I want to happen. This is hardly a revelation to anyone other than me, but there it is. I’m going to do it again.

So there’s that. I’m disappointed in your question, however. “You have a book coming out. Let’s talk about that.” Jeez, man, you sound like Billy Bush. Let’s step up the interrogation a little bit.
I’ll help you out. After years of toiling, you’ve become a big-shot blogger now. You’re all over the place? Are you having fun? Are you more professional fulfilled? Have you finally slept on a bed now? I am uncomfortable with both the term and the connotation of “blogger,” even though I now do one professionally myself. I am aware that I sound like a snot. That is the way of the samurai.





First, thank you for the Billy Bush comparison. It’s something I’ve been striving for. Either him or Bob Goen. I’m just glad you didn’t say “Pat O’Brien.” Coming up next, a behind the scenes look at American Idol!

“Professional blogger.” Sounds like an oxymoron, doesn’t it? I don’t know how much of a big shot I am though. I mean, you’re an A-list blogger but for some reason I’ve been stuck in the B-list for months. To be honest, I don’t consider myself a blogger. I mean, I can’t! I’m a writer who happens to blog. And like you I bet that sounds snotty too, but it’s how I feel. I mean, I cook a lot too, but I wouldn’t call myself a chef.

I still don’t have a bed Will. I’m still sleeping on a couch in the living room. It’s been over 7 years since I slept on a bed, and I think my body has bent into a shape that will make sleeping on a regular bed almost impossible. But I’m going to try. I’m moving from here in January. After so many years here (12), I’m outta here. Where? I have no idea. I’ve narrowed it down to some place between Boston and Alaska. In other words, I’m open to anything.

Catch sounds a lot like your real life.


Bob —

Bob Goen. I had completely forgotten about him. Is he still on the air? Or am I thinking of someone else? I really only watch sports anymore … TOO MUCH sports.

Well, I dunno: I’m making a living at this, and I don’t have any other jobs, so I guess I have to classify it as a “profession.” It’s strange to me to be considered a blogger, though, not because I’m some big fancy pants writer, but simply because I have been doing it for such a short amount of time. Before doing Deadspin, I had never run a blog, never even thought about it much, really. So many of the sports blogs have been doing what they do for much longer than I have, and I’m just trying to learn from them and bring my own thing to the table. Before Deadspin, like everyone else stuck in a boring desk job, I read blogs incessantly, but it had just never occurred to me to start my own, though I can’t quite remember why. But when the opportunity came up with Gawker Media, a group that (other than me) has a pretty impeccable eye for talent, it was too much to even think about turning down.
I can’t attest to the decision-making behind the A-list over there; the Blogebrity guys fascinate me, though. They do an outstanding job at making the people they write about it feel much more popular and important than they actually are. Which is a real service. In fact, I think they’re kind of ahead of their time. They are, essentially, a trade publication for blogs. (Since what a trade publication really is, deep down, is an excuse for people who aren’t famous to trick themselves on a monthly basis into thinking they are.) Do you realize there’s a magazine called Elevator World? They have a trade publication for people who build and repair elevators, Bob. It would be dumb not to have a trade publication on blogs. That it’s well-written, funny and overly obsessive … well, that just fits the mission, doesn’t it?

Every time I talk to you, Bob, you’re about to move. And that can’t be good for your back. People who have to bend like that often can find good side work at halftime of NBA games, though.
You know, people have said that about Catch, but when you read it, it becomes pretty clear it’s not really autobiographical, save for the setting (Mattoon) and the profession of the main character’s mom (nurse). I certainly worked from items in my life that I was familiar with — it’s not about, say, starving children in Africa, because I am neither smart enough nor deep enough to pull that off — but it’s fiction. Tim Temples (the main character) is considerably cooler than I was in high school. Taller, too.



In all honesty, this gig here at Weblogs, Inc (AOL, Will!) is the best writing job I’ve ever had. I mean, freelancing all those years…God. I mean, I get to watch TV every single day, write about it, and get paid! Wow, think about that. It must be the same with you. You get to talk about sports all day. But you have a real job too still, right? I would be watching TV all day anyway, so it’s great to actually get paid for it. I don’t feel so bad watching reruns of Celebrity Poker Showdown now. (Though it has seriously taken me away from my other writing, including my book.)

Will, can you pinpoint the biggest mistake you ever made in your life? I mean really pinpoint it? Mine was December 15, 1993. That’s the day I moved into this apartment. It’s like I’m waking up from some fever dream. It’s not that the apartment has been ALL bad, not at all. But its been a 12 year detour. I should have moved soooooo many years ago. Never had the money, had to stick around here for a job, whatever the reason. But now thanks to a steady gig and an incredidle desire to move that eminates from the souls of my feet, I’m finally going to do it. I have to admit it’s the most exciting thing that’s happened to me in years.

What are you drinking, by the way?


Bob —

Yeah, I like the guys at Weblogs, you AOL sellouts you. I used to work with Jason Calacanis at his old Venture Reporter magazine, and if that guy’s anything, he’s unfathomably energetic. What he’s been able to create over there, out of the ashes of the same flameouts the rest of us went through, is pretty amazing. I guess Weblogs Inc. and Gawker Media are supposedly rivals, but I think we’re all on the same team here. Rah team. I like him.

And yes, Bob, this is what I do full-time. Well, and I work on the next book. Slowly. I’m pleased to be out of the world of trade pubs. I tried as hard as I could, but I just couldn’t make myself care about Morgan Stanley. God did I try. Now I work out of home; I get up at 6:30, go to the gym, come back at 8 and type until it’s time to go to bed. (Or maybe take the lady out; I live with my girlfriend now, and it’s important to get her some sun and water and nurturing.)

I’m very proud of you for actually moving, Bob. Now you have to go out and do it. I wish you all the luck in the world. Twelve years, man. That’s crazy. Twelve years ago, I couldn’t grow facial hair … oh, we covered this already.

Oh, and I’m also drinking red wine, because way too many people brought red wine to our housewarming party and I gotta get rid of the shit somehow.




This is what I do full time too. I’m working on a book too, though I put it away for about 6 months and only recently pulled it back out. Ooooo, that sounds dirty.

So you’re shacking up with someone, eh? My dating life is so insanely bad. Imagine me going out some place and bringing a woman back to my…couch? How lame.

Working from home takes a little getting used to, but if you do it for a while, you won’t be able to go back to an outside job. I guess that’s both a good thing and a bad thing.

Another reason to move? I’m so out of the loop. Just to go to Boston for something I have to plan ahead lilke I’m going on some business trip. We’ve never met. I’d love to go to your book release party on December 3, but you insist on having it in New York City instead of down the street from me. Whatever.

I need to get laid.


Bob —

This is the point in the conversation when I remind you that you still owe my a book. Three years later. And I even paid for mine.

Yeah, been living with my girlfriend for about six months. It’s really not as hard as I thought it would be, or had been told it would be. She leaves the seat up too often, I leave cereal in the sink and that’s really been the extent of our difficulties. It helps that she is also a writer — an excellent one. She has a book coming out in April, and I can say this with 100 percent certainty: It’s considerably better than mine. This fact does not bother me at all, much to my surprise. I read her book for the first time and thought, “Hey, I can’t do this. There’s no competition. I couldn’t even think of pulling something like this off.” That realization has made everything easier. I’m crazy about her, and am extremely lucky. And no, she’s not sitting behind me right now.

Honestly, I can’t imagine going back to an office job, which is a stupid thing to say, since it’s nearly certain that someday I will have to. Do you realize how many fewer inane conversations I have about the Mets now? I get so much more work done without anyone around, and that’s a fact. Eventually the American workforce will realize this. Hopefully I will have continued to successfully avoid offices when we get to that point.

I’m actually going to be in Boston in March for a reading. It’s ridiculous we haven’t read. And you’ve had opportunities too, Bob. I’ve done two readings in Boston; missed ’em both, Bob! But yes. A real reason to move. Do it.

You should move here, Bob. It’s much easier to get laid here. You’d really be surprised.




I can tell you’re drinking. SHE leaves the seat up? It’s ridiculous we haven’t READ? Heh.
In all fairness, one of the times you were in Boston you sent me a reminder to me at the wrong address. But March sounds like a plan. I’ll be living some place else, so it will be easier.
Working from home is both a paradise and a curse. There are the constant interruptions of the phone and deliveries and people coming to your door and the fridge and television. But you don’t have to shave every single day, you don’t have to wear a tie, and you get to masturbate a lot. It’s a win-win, really.

I have this theory: I’m no Brad Pitt, but if I lived in NYC or Boston I think my number of dates would double. (Zero to any number of dates meaning “doubled.”).

Did you actually pay for a book? Jesus, I truly don’t remember getting any money from you, but I’ll take your word for it. It’s been 2 years, 3 months, not three years! God you exaggerate. Ha. If it’s any consolation, there are three other people who paid and still haven’t gotten the books yet. At first it was lack of money/materials to mail the thing; now it’s just the fact I keep forgetting, it’s been so long. But I’m going to give the people back their money. It’s the right thing to do, as Wilford Brimley used to say.


(No, no, that was a joke. Girls don’t leave seats up. I thought it would be a funny line. I did type the READ wrong, though.)

Wait, what? Did you go to the wrong place? I didn’t send you on a wild reading goose chase, did I?

Uh, sorry.

I’ve actually been pleasantly surprised by the relatively minuscule number of times I masturbate while being home by myself all day. I kind of thought it would be like summers when I was 15, which was pretty much daily mutilation. I think it’s just keeping busy and not the inevitable loss of sex drive as I enter my 30s. That’s what I’m telling myself.

I don’t want my money back, Bob. I want a book.

Illinois game starts in 15 minutes. Better wrap up soon. You do seem to be getting along better these days, sir. Do you feel like you’ve finally made some headway? I know it’s been a long struggle, for the both of us, I guess.




Heh…no, I meant you send the reminder to the wrong e-mail address and the date passed without me knowing you were in Boston. So we haven’t met yet. But we will, we will.

Don’t mention to me about being in your 30s. Did you know I hit 40 last June. 40! Keep saying that to yourself.

I do feel like I’m actually ahead now. Not just some uncomfortable middle ground where I’m existing but not enjoying my life. Things are actually sensational. I honestly thought at one point I would give up writing and get a full time job doing something else. Selling shoes or something. But I’m doing what I want to do. Moving is the next piece in the puzzle.

While you’re watching college basketball, I’m watching Home and Garden TV, tips on how to decorate your home for the holidays. Like I said, I need to get laid.


(45 minutes later)


Sorry. Got distracted. Basketball. You bombed?


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