I recently wrote a piece on TNB about my entirely earnest and ultimately unsuccessful attempt to sleep with actress and comedian Janeane Garofalo. I made my case to Ms. Garofalo – that I felt very strongly that she should sleep with me – in the form of certain letters, published in the pages of an understanding Melbourne street magazine, while she was here to perform at the city’s annual International Comedy Festival.

Sadly, she was not persuaded, and I was forced to make do with stealing a frogurt from Crista Flanagan.

Now overwhelming public demand (and by overwhelming public demand, I mean two people, but that’s one more than enough for me) has induced me to republish those letters here. I must warn you – even if you are not Janeane Garofalo, you may very well find yourself seduced.



Dear Janeane Garofalo.

I was delighted to hear you are attending this year’s Melbourne Comedy Festival this year, as, deep in the burning and well-dressed depths of my soul, there is a question I need answered, and I think you are the person to answer it, and that question is this:

When am I going to have sex with Janeane Garofalo?

You see, Janeane Garofalo, I have so very many reasons for wanting to sleep with you. For a start, I need an American media connection to help catapult my collection of stories about Hollywood actress Clea DuVall having super-powers into publication and, subsequently, into the annals of publishing history. And I think our sensual pairing (yours and mine, Janeane Garofalo, not Clea DuVall’s and mine, unless she is at the Comedy Festival too, in which case I will win both her trust and her love by casually striking up a conversation about Leisha Hailey’s band Uh Huh Her) would be a great ice-breaker, or at least a good cure for those awkward moments of silence at dinner parties.

‘Well!’ I’ll say, chuckling heartily, possibly over the canapés, which I assume will be delicious, ‘It certainly wasn’t this quiet when Janeane Garofalo was dislocating my ribs! While we were having sex.

Piquant decorative hors d’ouvres notwithstanding, you better believe that’s going to turn some heads.

You needn’t worry about a thing, Janeane Garofalo. I’ve been going to the gym for some time, and I’m not like those skinny ‘writers’, ‘actors’, and ‘firemen’ of your acquaintance. No. No, you will thrill to the touch of my manly biceps and impressive shoulders, you will find your every future dinner plate ruined by the memory of my deep and proud pectorals, and you will most likely want to take some time during that period normally reserved for pillow talk to admire the steely lines of my forearms, thighs, and jaw. You will also be astounded by my skills as a lover, especially as I sexily whisper ‘I haven’t enjoyed myself this much since 1997’s The MatchMaker,’ in your ear mid-coitus.

You’ll like me, Janeane Garofalo. I listen to David Cross’s comedy albums. I’m above average height. I’ve lived in San Francisco (and, mark my words, I shall live in San Francisco once more). Also, I watched W once.

And I will cook for you, Janeane Garofalo – and I don’t just mean I’ll serve you up a delicious three-course meal of hotel-room-deposit-voiding sex, although that will certainly be on the menu. No, I will find you only the most delicate pastas, the most sensuous garlic breads, and the least virginal virgin olive oils, and I will prepare you a feast.

I’m not a particularly competent chef, so it’s not going to be very good. What I possess in attractive musculature, I lack in culinary prowess. So, you know. Due warning.

The good people at Beat Magazine have my phone number, Janeane Garofalo. Feel free to dispatch one of your flunkies to collect my contact details; the editors give them out all the time anyway, often after the sixth or seventh Harvey Wallbanger has glazed their eyes over lunch, their French drug dealer Pierre has crawled up through the secret hatch in the floor, coughing up dust and cobwebs and bearing the day’s shipment of finest Scandinavian Bronze, and someone has, once again, put Eagles of Death Metal on the office sound system with the cry ‘Hey everyone! Let’s all have sex to this!’

Let’s all have sex to this indeed, Janeane Garofalo. Let’s all have sex to this indeed.


Simon Smithson



Dear Janeane Garofalo.

I find myself looking at the calendar with some alarm. As near as I can figure it, you will only be in town for a few more days, which is barely enough time for you to fully appreciate the level of toning that I have brought to my glutes (and let me tell you, Janeane Garofalo, I have not merely focused on my gluteus maximus. Both my gluteus minimus and my gluteus medius have received the most exquisite care a gold card membership at 24 Hour Fitness can buy, and you will be impressed). Our window is closing, and closing fast – especially as you have shows to do, and I’m going to be devoting some fairly solid blocks of time to catching up on Supernatural.

It has been a cold, hard week for me, Janeane Garofalo (although not quite so hard as my glutes, a fact which has provided me some small comfort). My strong arms yearn to hold a liberal American comedienne, and both you and Amy Sedaris seem so very far away. Every morning when I wake up and look over and you are not sleeping, sated and satisfied, beside me, is a morning when the world seems a little greyer, and I am quick to let whoever is sleeping there know just how disappointed I am.

Because it’s not just about your fame, Janeane Garofalo. It’s not just about your willingness to take on the American conservative movement. And it’s not just about your wit, or your verve, or your role as The Bowler in Mystery Men.


It’s also about the sex.

And, if the blogs I write about my own performance in the bedroom are anything to go by, then let me assure you that I’m pretty good. One second we will be making conversation, quite possibly about how handsome I am, and the next… well, let’s just say that I will be bringing at least one Soul Coughing album, and maybe more.

Although they only released three.

Perhaps you are worried that I’m only using you to get to Kiefer Sutherland, Janeane Garofalo. Let me assure you, nothing could be further from the truth. The sacred moments that we share in your hotel room after the sun has gone down and the cool darkness winds around us will be for you and I alone. Although I probably will ‘accidentally’ leave behind a couple of unpublished manuscripts. In your suitcase.

Feel free to read said unpublished manuscripts on your long flight back home, Janeane Garofalo. I have learned from bitter experience just how arduous that flight can be, and I know that I myself spent much of it thinking to myself Jesus Christ, I wish I had something written by a handsome Australian writer who had shown me hours of passionate attentiveness and dutifully followed my every instruction, as well as bringing some surprisingly spontaneous manoeuvres of his own to the table, to read right now.

I’d spare you that pain, Janeane Garofalo, if I could. And the best part is, I can.

With gusto.

I’m taking instruction from late eighties supernatural comedy Hunk, Janeane Garofalo. I’ve been reading nothing but Hemingway, and, occasionally The Far Side. I’ve been eating protein bars, and oysters, and brutally undertipping waiters if they offer me anything but Gatorade to drink. Like Obama’s stimulus package, I’m ready to roundhouse punch my way to victory, although I’m not entirely sure what that analogy means. All the protein and zinc supplements I’ve been consuming have left me feeling a little dazed.

I yearn for you tragically,

Simon Smithson

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SIMON SMITHSON is an Australian writer and editor. He is currently based in Melbourne, Australia, but frequently finds himself in Los Angeles and San Francisco. His work has appeared on both sides of the globe in print and online in publications such as BLIP, Every Day Fiction, Beat, The Loop, My Sinking Boat, and more. He has a tumblr at www.simonsmithson.com and he runs a lifestyle experiment at www.selfhelpless.net.

28 responses to “The Letters I Wrote that Did Not Convince Janeane Garofalo to have Sex with Me”

  1. Zoe Brock says:

    She’s clearly insane. Or very very shy. Or gay.

  2. I don’t care one little bit. I just have to believe in myself, and I can achieve anything.

  3. […] Hall of Fame In a piece entitled “The Letters I Wrote That Did Not Convince Janeane Garofalo to Have Sex With Me”, author Simon Smithson uses an epistolary approach to try to get Janeane Garofalo to have sex with […]

  4. Ducky says:

    You go, Simon. And then persuade her with your manly ways to be in one of my movies.

    I fully believe I’ll fuck Bill Maher one day. We’ll listen to all his records and smoke a lot of weed and then we’ll get busy. Fully believe this. Even know what shoes I’ll wear.

  5. Ducky says:

    btw – I have a story about her – well sort of. I had wanted her in my first film, pitched her agent, even had dinner with him. He loved the project and wanted her to make a “comeback” with it. (Like she went anywhere!) But then she fired her agent. So…fuck me.

    I still want to work with her one day. She’s got great timing.

  6. Megan DiLullo says:


    It’s seems as though most men love Janeane Garofalo. And of all the stories and podcast I’ve heard of men trying to woo her… Simon, you’re the one.

  7. I love this! I particularly love, dear Simon Smithson, how you refer to her always with her first and last name. Was there a picture posted of you with the letters? Certainly would have helped. How many women wrote in and said that they were not Jeneane Garofalo but they would be happy to have sex with you and pretend to be Janeane Garofalo?

  8. Matt says:

    I cannot read this without hearing your presentation of it in L.A., which was just classic. Lucky me, I shot that footage and still have the file saved to my computer. So I can pull it up and read along as you narrate. It’s an Interactive Smithson Literary Experience! Win!

  9. Simon,

    Color me seduced. I tried to fuck Julia Roberts once– got as far as winking at her while serving her taco salad in Taos, New Mexico. (It was really good taco salad). My wife is still trying to fuck Bruce Springsteen via emails to his (doubtlessly turned-on) publicist. I’m going to suggest she copy you…

  10. […] reading a letter her husband wrote on a Web site whose influence, while mighty, was insufficient to convince Janeane Garofalo to boink a handsome and debonair Aussie fifteen years her junior…hey, I understand. I won’t take it personally. But if you’re willing to give it a shot, have […]

  11. […] a mysterious woman(?) named “L.” *Melissa Febos writes a love letter to Uncle Sam. *Simon Smithson writes to Janeane Garofalo, inviting her to have coitus. *Alexander Maksik writes an epic love letter. *John Singleton writes to the Excellence in Teaching […]

  12. Gloria says:

    “I yearn for you tragically” is the single greatest line ever written, and I shall use it.

    This is some ridiculously funny shit, Smithson. I seriously hope Janeane Garofalo goes after the good stuff. And soon.

  13. […] Lover, but not of Janeane Garofalo. […]

  14. […] reading a letter her husband wrote on a Web site whose influence, while mighty, was insufficient to convince Janeane Garofalo to boink a handsome and debonair Aussie fifteen years her junior…hey, I understand. I won’t take it personally. But if you’re willing to give it a shot, have […]

  15. […] Straight talk from SIMON SMITHSON, who, by the way, has yet to boink Janeane Garofalo. […]

  16. jack droe says:

    well? Did you manage too coo her into submission? Been a few years now.

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