7 emails I really wish I could have unsent

God damn it, Google. Now you take the “Undo Send” feature out of Gmail Labs and publicize it to all your users? Where was this nifty little trick when I could have actually used it? Because I can’t tell you how many times my life was ruined beyond repair by admittedly ill-advised emails.

Well, I suppose things can’t get any worse than they are, so I’ll just share my biggest Gmail mistakes with you. With another 60 seconds to think these missives over after pulling the trigger, everything might have gone differently for me. Instead I am doomed to endless misery.   

1)

From: [email protected]

To: [email protected]

Re: bearded cutie on 4 train    

Hi there! I saw your w4m missed connection about a cute guy with a beard on the 4 train who was reading a book about urban planning. I wasn’t reading a book about urban planning, but I was recently on the 4 train—maybe you meant me? Look forward to hearing from you!

Love,

Miles

2)

From: [email protected]

To: [email protected]

Re: bearded cutie on 4 train    

Oh my god, I did not mean to sign off with “love” in that last email. Totally inappropriate. I had just been emailing my mom, so it was probably force of habit. LOL. That’s almost as bad as telling you right off the bat that I think you have a sexy butt (which you do, if you’re the woman on the 4 train I’m thinking of). My bad.

Love,

Miles

3)

From: [email protected]

To: [email protected]

Re: bearded cutie on 4 train       

WOW, I cannot believe I wrote “love” again. Where is my brain today?! Sorry about the sexy butt thing, also—I realize now that what I thought was a joke about saying you had a sexy butt is really, in effect, saying you have a sexy butt, which I would normally never do until halfway through the first date. Kidding! (No I’m not!)

Love (jk),

Miles

4)

From: [email protected]

To: [email protected]

Re: bearded cutie on 4 train

OK, I think I may be sending mixed messages here. Let me just say, on the record, that I am interested in much more than your sexy butt. I can definitely talk about other things. Like, do you really want to date that bro reading about urban planning? It’s just such a dry topic. It’s probably his whole life, really; doubt he has time for anything (or anyone else). Alternatively, if you’re into urban planning yourself, could you recommend me a book about urban planning? I’ve always wanted to get into it. If I didn’t mention it before, I am going to be an urban planner someday.

All best (nailed it!),

Miles

5)

From: [email protected]

To: [email protected]

Re: bearded cutie on 4 train

Look, I need to come clean. I don’t know what the fuck urban planning is. Also, I don’t have a beard. It’s not that I shave every day—I never do, in fact—but I only get these wiry, straggly hairs around my Adam’s apple. I’m so sorry. You don’t have to reply to this.

Apologies,

Miles

6)

From: [email protected]

To: [email protected]

Re: bearded cutie on 4 train

IT’S BEEN 12 MINUTES SINCE I STARTED SENDING YOU EMAILS AND YOU DON’T EVEN HAVE THE DECENCY TO RESPOND?!! WHAT THE ACTUAL FUCK?!!!! WHAT IS THE WORLD COMING TO. YOU’RE NO DIFFERENT FROM THE REST OF THEM, ARE YOU. YOU WALTZ THROUGH LIFE AND TAKE WHATEVER YOU WANT AND WHEN A STRANGER WHO REALIZED HE COULD CONTACT YOU THROUGH THE INTERNET DECIDED TO POUR HIS HEART OUT TO YOU, YOU SIMPLY GIVE HIM THE COLD SHOULDER. DIE IN A FIRE!!!!!!

DIE AGAIN,

MILES

7)

From: [email protected]

To: [email protected]

Re: bearded cutie on 4 train

Hi there! Um, did you get any weird emails from me recently? Pretty sure I got hacked.

Love,

Miles

Photo via Alexander Lyubavin/Flickr (CC BY 2.0)

Miles Klee

Miles Klee

Miles Klee is a novelist and web culture reporter. The former editor of the Daily Dot’s Unclick section, Klee’s essays, satire, and fiction have appeared in Lapham’s Quarterly, Vanity Fair, 3:AM, Salon, the Awl, the New York Observer, the Millions,  and the Village Voice. He's the author of two odd books of fiction, 'Ivyland' and 'True False.'