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Online dating messages gone bad: A date and free pie?

Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Oh I love internet dating and all the messages that people send.

Of course that means I have one to share. Though, this time the message did not offend me nor was I completely confused about what the guy is taking about. Nevertheless, it is a fine example of an internet dating message gone really bad.

close-up of a slice of pie with ice cream and a cherry garnish

Subject line: Free Pie

Message: Alright seriously...there is no pie but I thought this would help you open and this maybe chat with me later. Who knows we could get real pie in the future, or if you don't like pie maybe ice cream. Either way you're now thinking about sweets and will remember this message and either message me back from the sheer awesomeness of this note, or you you will blame me for massive weight gain from eating awesome sweets because this note was awesome. so I might be awesome and you're proabably awesome especially if you message me back I hope to hear from you soon

Before I say anything, I would like to thank this fine gentleman for the clarification that he is not actually offering me free pie in this message. Though if I had been expecting that when I clicked on the message he would have clearly wasted my time. Little does this guy actually know that I don't even like pie, but we can't really count that against him. And of course he did take in to account the fact that I might not like pie. Thoughtful, really.

Though, who in the world actually thinks that a subject like "free pie" is really going to break the ice? Sure, maybe he is going for that whole funny thing but I would have to say he failed. And clearly I would take it any day over being told I look like I'm DTF. But really, you sat down to write a message to a chick on a dating site and thought to yourself that talking about pie was definitely the way to go.

I am a big fan of the word awesome, I really am. However, I counted it, what, like five times in the last two sentences? Not very awesome at all buddy, really. And why am I awesome especially if I message you back? Maybe he was just trying to be cute. Obviously I am not as awesome as he thought because I did not bother to message him back. Damn, so close.

For the love of god will someone please teach people how to spell and use proper punctuation. I don't expect perfection, I truly don't. Seriously though, this is your big moment to make an impression on me. Wouldn't you want to take the time to maybe read through the message once before you click send?

I should also add in here that the picture of this guy was quite creepy. Someone really needs to tell him that posting a picture where you look mean and angry (especially when it's your one and only picture) is not your best laid plan. Actually I am a little disappointed that I couldn't include it with this post.




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Deanna Leigh said:

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Okay, so the message is ridiculous! I mean seriously? There's a way to do humor and keep it clever and cute and then there's just lame. Too bad cause I had a guy ask me out of pie as a first date and it was cute and sweet. And I totally agree, people don't stop and think before they press and have taken the time to re-read and edit their emails. Ugh.

Jessica Downey said:


I know, it is! I totally agree about doing humor and being cute. For example, one time I had a guy send me a message about how he thought he was the perfect man for me but that he was lame (I had it in the "you should message me if" section on OkCupid that the guy shouldn't be lame). I thought it was funny and it was obvious that he was being clever. Pie as a first date is really cute though, it's fun and out of the ordinary. This guy just needs a little tweaking I think.

Joe the Cop said:


Your comment about spelling and punctuation remind me of a presentation I attended yesterday. The instructor was giving advice on submitting writing for publication, and talking about communicating by email. He said there are a surprising number of people who compose email like they're texting, complete with "u" instead of "you", "r" for "are" and little smiley faces thrown in as well.


Jessica Downey said:


I do get a number of messages that are like that on internet dating sites and I am a little shocked that people do it in emails as well. It drives me nuts! Like it's that much harder to just spell out the word "you". I think people sometimes forget what text chat was invented for. Thanks so much for the comment!

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