The 5 Dumbest Emails Of All Time

Online Dating

The 5 Dumbest Dating Emails of All Time

Gina Stewart

Written by: Gina Stewart

Gina Stewart

Gina is the owner of Expert Online Dating. As an online dating consultant, she helps men and women maximize their online dating experiences to get more dates. You can visit her website,, for more information or to contact her.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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It’s often been bemoaned about what women have to put up with in emails from men when online dating.

Consider this your PSA to just how weird some of them can be.

5. The male Annie Liebovitz

A woman would read this email as, “Even though your photo is bad, it’s the best one.”

Don’t send an email to a woman pointing out flaws, and unless you’re writing a poem about the sun, “hot spots” should never be a conversation topic.

This deluded guy doles out an insult but tries to pass it off as knowledgeable, constructive criticism.

This isn’t a photography class, and this does not make a woman swoon. I actually think he’s a frog.

4. Mr. Sexy Sex Time Talker

Unfortunately this email is a single drop in a tidal wave of sexually explicit emails women receive while online dating.

Men lead with lots of promises of how lucky they can make you. Between promises of a van, magic massages and that “masterpiece” of a body of his, you can guarantee Mr. Sexy had one promise right: a night of bad decisions.

3.  Dan likes public farting, strippers and public transportation!

I don’t think I need to say a thing about Dan that Dan hasn’t said himself.

Ladies, please don’t email us asking for this guy’s contact info. We aren’t sure our servers can handle that level of traffic.

2. Cat poos and funs

I can’t help but imagine the light bulb moment when Tyler thought to himself, “I know how to attract women! It’s got to be by talking about cat pooped sheets in marbled English!”

I have hope for him, though. I think Tyler’s perfect woman is on an episode of “Hoarders” somewhere and looking for “funs” as well.

1.  Sex shenanigans and Civil War photos

While a lot of guys just send a “Hi, how are you?” email, this guy does a bang-up job of carving out a niche for himself.

He can tell you about all the old black guys and their hilarious sexual escapades. One can only hope those shenanigans don’t involve him personally, but maybe he’s really trying to showcase his ultra-unique lifestyle. All the while, his photo looks like he’s from 1863.

This guy is a rare find, ladies. Don’t let another 150 years pass before you give him a chance. He just may be a vampire like Edward in “Twilight” or Bill in “True Blood.”


Sound off! I know there have been some crazy emails sent your way. What have people told you?

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