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A Series of Letters to the First Girl I Ever Fingered

By Michael Ian Black April 13, 2007 151,832 views
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Dear Emily,

Hi! How are you? I hope this letter finds you well. I don't know if you remember me or not, but I'm the guy who fingered you at sleepaway camp.

Anyway, I was just thinking about that, so I thought I would write and see how everything turned out with you.

Your Friend (kind of),

Michael Ian Black

Dear Emily,

After not getting a response, I have become very worried that my last letter somehow offended you. Confused, I reread what I wrote several times, and finally came to the conclusion that, if you were offended, it was probably the part about fingering you that did it.

If so, I am very sorry. Not about fingering you (which was great), but about referring to it so candidly after not communicating with you in over 20 years. So, I'm sorry. In the future, if I refer to fingering you at all, I will try to be a little more discreet.

Very Sorry,

Michael Ian Black

Dear Emily,

Hi, it's me again (the guy who f-ed you). Still haven't heard back from you. Is everything okay between us?

Write Back,

Michael Ian Black

P.S. That's a rhyme - "Write Back/Michael Ian Black" LOL!

Dear Emily,

Oh my God! I just realized that when I said I "f-ed you" in my last letter, that easily could be read as "fucked you." God forbid your husband or lover (lesbian?) should read that! If that person IS reading THIS letter, I did NOT fuck your wife/lover. I just fingered her. I was just trying to be discreet about referencing it, which is why I used the initial "f" for "fingering." Total brain fart!

Please tell Emily to write me back. Or Emily, if you are the one reading this, sorry about calling you a lesbian in the previous paragraph (unless you actually ARE a lesbian, in which case I am TOTALLY cool with that) Did my fingering you turn you gay? I hope not.

Sorry Again,

Michael Ian Black

Dear Emily,

Still no word from you. I feel like maybe we got off on the wrong foot right from the get-go, and I'd like to try to make it up to you.

Let me start over, and if you still don't want to write back, I will definitely understand.

(Starting over):

Dear Emily,

Hi! How are you? This is Michael Ian Black. We went to camp together a long time ago. In fact, we kind of "dated" one summer. Pretty funny, huh? I don't know if you remember me or not, but I definitely remember you. In fact, I have many fond memories of walking around the lake with you, playing knock hockey with you in the canteen, and also finger popping you.

The truth is, you were the first girl I ever fingered, and I still think about it all the time. Please take that as the compliment that it is intended to be, and not as anything "weird" or "creepy."

(Believe me, I could easily see how receiving a letter from a 35-year-old man reminiscing about fingering a 13-year-old girl could be construed as inappropriate. It was DEFINITELY not intended that way)

Anyway, if you get a moment, I'd love to hear all about your life. Do you like dogs?

Your Friend,

Michael Ian Black

Dear Emily,

It's starting to become clear to me that you have no intention of writing back. At first I thought it was because you were shy, and didn't know what to say in your letters, which is why I ended the last one with a question designed to begin a dialogue ("Do you like dogs?").

However, now I'm beginning to think you just don't want to communicate. Maybe you told your husband that HE was the first guy who ever fingered you, and these letters are a painful reminder of the lie you are living.

If that's the case, I DEFINITELY understand. I was once in similar position with a girl who wanted to put something (a small jar of martini olives) up my ass. Of course, I told her she was the first. But believe me when I tell you, she was FAR from the first.

I lost touch with that girl a long time ago, but if she were to write to me today, I think I would at least have the courtesy to write her back.

I hope you die.

Michael Ian Black

P.S. If you do die, I'm going to go to the funeral and finger your corpse.



LOL as soon as I saw that her name was Emily, I was like "woah, coincidence?!" because whenever i hear of anyone getting fingered I think of this girl, Emily, who got fingered by three random guys at a party, and she used to be my best friend but she's liek a s**t, so yeah (oh and it happened when we were 13)

9/20/2009 9:49:55 PM
CitizenDildo

Haha. These letters actually remind me of this guy who won't stop writing and over-explaining his feelings to me. Especially that last letter. Man, if we ever "got it on," I bet the result would be a lot like this...

P.S. I love Michael Ian Black.

12/26/2008 11:30:50 AM
greedymuppet

I am such a big fan of you since last year. Wish everything goes well for you. Can you do me one favor? just tell me is it you on****** W e a l t h y s o u l M a t e .C O M ********** ?

11/30/2008 5:39:58 AM
oscarfeng

omg super funny

11/29/2008 8:42:04 PM
jamiiibbe

Michael Ian Black is hilarious. Love his work. Maybe it's just me, and my own fucked up experiences, but I thought it would have been funny if he apologized for not having trimmed nails and that she's the reason he now keeps them nice and neat after the "incident."

11/27/2008 4:08:18 AM
Mojomajik9

I recall writing a series of letters like that once. That b***h didn't write back either... Stupid whores...

11/26/2008 7:56:19 PM
Sodomy

That was pretty great.

11/26/2008 3:19:15 PM
Swaimfan

That was brilliant

11/26/2008 12:21:25 PM
Laurara

This is absolutely hilarious in a totally disturbing way! Awesome!

11/26/2008 9:45:08 AM
griffmanr

Truly brilliant! You're a sick man! I like that!!

11/26/2008 2:07:29 AM
Darkmage

I think I am one of the few people who like Michael Ian Black is hilarious. I laughed throughout this whole thing. It must be one of those things you either get or don't.

11/25/2008 11:26:35 PM
jaasum

Michael Ian Black grows on you. He used to post his stuff on MySpace. Then he and the rest of the internet grew a collective brain and started posting in dignified fora such as cracked.com

11/25/2008 10:51:24 PM
Brownian

I swear I read this awhile ago, but not exactly sure where.

11/25/2008 8:51:45 PM
shzk

This is truly disturbing.

11/25/2008 6:41:38 PM
jerrylambert

I can't stand this guy. Why do people think he's funny?

11/25/2008 3:57:00 PM
phuchuebuddy

I can't stand this guy. Why do people think he's funny?

11/25/2008 3:56:55 PM
phuchuebuddy

i didnt know MIchael Ian Black a heterosexual!
life just keeps trowing curve balls at me all the time.

11/25/2008 1:02:28 PM
hlcom30

I thought that jar of olives slid in just a little too easily. And I just thought you had a greedy bum. But you didn't have to tell me I was the first. To make it up to me, could I be the last?

11/25/2008 12:02:37 PM
YellowPages

Dear budd519:

You're a DOUCHE.

The end.

11/25/2008 11:28:55 AM
BeckiMars

This was actually funny. Crude, yeah, but it's not like anyone could have been expecting something else. Not bad.

11/25/2008 11:09:46 AM
Tartra
Cracked stuff on