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A Series of Letters to the First Girl I Ever Fingered

By Michael Ian Black April 8, 2008 75,790 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.

If you like that you might enjoy the story of how we got on The Judge Joe Brown Show and talked about transvestite strippers. Or read Wayne Gladstone's latest post in which he comes dangerously close to using the word whippersnapper.



Finger f*****g a corpse makes everything funnier.

3/21/2009 2:22:04 PM
NerdyNinja

this article was WAY funnier when Michael Ian Black did it on that Comedy Central "My First Time" episode

4/10/2008 5:02:17 PM
Theman.com

Everyone likes (or should) Sigma!

4/10/2008 11:28:34 AM
Ranger

i like sigma

4/10/2008 10:23:50 AM
Gemineye870530

This is Emily, you actually just forgot to include a postal address for yourself

4/10/2008 3:15:09 AM
bebophile

So I'm pretty sure that this was ripped off from a short story Steve Martin wrote in his book "Pure Drivel"

4/9/2008 10:49:27 PM
IrishTerror

ooolllllddd....

4/9/2008 6:38:45 PM
Ubermensch

ohh..damn artical,seems it has no good content,i also read a hot loving letter from a friend playing on tall dating site:" Tallmingle.com ",that is great ,he got a beautiful girlfriend by this letter.

4/9/2008 6:12:52 PM
ella1984

what the f**k? I read this last year, it was one of the first articles i read here :S

4/9/2008 1:49:53 PM
luis1210

This article was pretty damn funny. When I read it last Summer. You guys at cracked are a bunch of lazy, shiftless, ignorant pieces of doodie. Anyway keep up the good work.

4/9/2008 1:01:44 PM
Warcry81

LOLZOR. You should read the Timewaster Letters. Funny book, same kind of thing.

Peace and Love to the brethren.

4/9/2008 11:09:09 AM
BigEasterCake

A tall dating site perhaps? ;)

4/9/2008 8:58:50 AM
Sigma

I could swear I read this before on another site...

4/9/2008 7:14:37 AM
darkhorse08817

I could care less if i'm loved on the internet. The comment section is for people who've read the article to voice their opinion. I voiced mine, you voiced yours. You seem bitter... have you had your juice today? You may need a nap.

4/9/2008 7:11:32 AM
Sigma

Hold on a second... this article... it didn't have a list! How..how am I supposed to understand comedy in a non-list format! This confuses and enrages me!

To further spit in my face not only is this not a list but it dosen't reference any wacky celebrities! I think you should change this title to 10 Things Britney Spears is Stupider Than! and rewrite the article accordingly.

4/9/2008 6:03:22 AM
NPJ

do you like dogs?

4/9/2008 5:48:34 AM
MagnuS

sigma, you need to shut the f**k up! you think nothing is funny. and you should go suck a dick or something. No one here likes you.

4/9/2008 5:15:16 AM
a dumb faggot

ok, the olive jar was funny... but THAT'S IT!

4/9/2008 4:53:54 AM
Sigma

I had no clue this was a repeat but since i was bored to tears i'm sad to learn it is so.

4/9/2008 4:49:09 AM
Sigma

Michael would probably use that rubber fisting glove shown in a list a few weeks back.

4/9/2008 1:15:07 AM
Haruhi