Sample Online Dating Email Messages

Lately I have been getting really good at having great flirty conversations on PlentyofFish. I've found that the most successful email message exchanges, regardless if I initiate contact with the girl or she does, is all about banter.

What do I mean by "banter?" Well to put it simply, it's a kind of humorous, playful, seemingly spontaneous conversation in which both parties are in good spirits. It is also kind of like teasing in a sense, you know, like when you were a little kid on the playground and that girl or boy would punch you in the arm for no reason, it's because he/she really had a crush.

I'd like to share one sample conversational email thread with a cute girl who had actually contacted me, asking a simple question about my dating profile, which is filled with interesting conversation bait as any good online dating profile should. The names and certain details have been changed to protect the innocent and not so innocent (I'll let you decide who's who:-). Also, I will be adding my own commentary afterward in the blue writing to explain what is going on in my diabolical mind.

Email Message #1: From Jane
I'm curious how your marathon went. Did you find minimal padding was ideal or were you aching afterward?
You seem very unique, and interesting.


Now right off the bat, I have a cute girl contacting me all because I put in a ton of effort into my dating profile. There's all sorts of interesting stuff that I've written and re-written, one of which is about my running/marathon hobby that baits her into sending me the first email message. Also note that she calls me "unique" and "interesting" so you know that I've got her attention, which makes the whole process a heck of a lot easier.

Email Message #2: From Me
Hi Jane,

The marathon went well and though I was sore afterward, the recover was shorter than usual. I do believe that minimalist shoes allow your feet to move more naturally and is beneficial to creating a more efficient foot strike. I've done a lot research and self experimentation in this area; it's pretty interesting stuff. Are you a runner?

Also, I've been trying to figure out what the heck that costume is in the third picture of your profile... lion king outfit??? :)


Ok, there are two parts to this and both are pretty important. Most guys royally screw up here by either saying something sexually offensive or spilling their guts with a boring ass life story, possibly professing their love for this girl that they haven't even met.
First thing I did was to answer her question briefly but also in a way that shows I know a lot about my hobby, running, without being arrogant. Second thing I did was to make sure I ask her a question or two. This step is important because it allows her to easily continue the conversation and keeps things moving. Also, if you ask her a specific question about her profile, it shows that you actually read it and paid attention to something other than her boobs!

Email Message #3: From Jane
Amazing, but I suppose it shouldn't be so surprising. In high school I was forced to be a runner, and sort of continued after but to a much lesser degree.

I have nooo idea what it is, it has horns so maybe a mountain goat of sorts? I was in charge of organizing an attic full of costumes that the high school drama club and the local community theater uses and...that happened :-P.


Ok good, she took the bait from the last email message and responds with some more interesting things about herself, yet still she doesn't do much to keep the conversation rolling, so in my next email I'll have to get more creative.

Email Message #4: From Me
Ha ha, well, whatever it is it's funny. You seem like you might be prone to getting into mischief... like the kind of girl who'd explore their parents' forbidden attic or that old creepy abandoned house down the street.

Pop quiz, where would you rather go exploring: a distant mountain range, a tropical paradise, a vast wilderness or the urban jungle of a foreign city?

Extra points for being creative:)

This is where I drop the bomb and go all in. This is what I like to call a qualifying email message. The reason it's called a qualifying message is because it's designed to elicit an answer that will allow me to either filter her out as a girl that is not my type or gives her a chance to show me that she is my type. Note that this is designed for me personally and would be different for other people based on whatever their preference in dating type.

Email Message #5: From Jane
A little trouble is good for the soul. I love abandoned houses, I just try to avoid the illegal actions (breaking and entering and such).

I love mountains, last month we went to trail days in damascus,va and that is a beautiful place to explore, but what's more interesting is digging through the people. There were so many different "types" of people all with fascinating stories. I adore cities also, back alleys and finding those amazing restraunts that no one else realize is there, or the authentic belly dance shop that draws you in (or whatever your passions may be at the time). I find it's a lot like antiquing, when you find something that looks like junk but inside is marvelous (I greatly enjoy going to garage sales like that too).


Wow, she sounds super awesome right? She really gets into it and was able to elicit a personal and emotional response. She is revealing stuff about herself that she wouldn't if she wasn't attracted and interested in meeting me. She passes the qualifying question and the only thing left to do is to put the nail in coffin and arrange the meet up.

Email Message #6: From Me
Wow, you are adventurous, I think we need to start an explorers club, what do you think? How about we make our first adventure to get some ice cream cones?

There's no need to keep the conversation now, the only goal is to get her number, real email or other contact information. Too many people get stuck in the online dating forever zone which seems to be a consistent problem. Your goal with online dating on sites like Plenty of Fish isn't to make a pen pal, it's to get dates in real life! So rather than let things fizzle in the virtual online realm, you need to move the interaction to an actual real date as soon as you've created attraction.

Email Message #7: From Jane
That would be great, you can call me this evening, here's my # (555) 555-5555


It worked!!!  Not only did it work but it was done in only 7 email messages.  There you have it folks, one of my best examples/sample of successful online dating email messages from where else but the PlentyofFish dating site.

Vegetarian Singles vs. BBQ Singles

Are you having trouble looking for dates with high I.Q.s and great bodies? Well, all you have to do is a search on your favorite online dating site for the word "vegetarian." Yup, that's it, one simple search for vegetarian singles and you easily narrow down the gene pool to the hottest and brightest. What's that? You think I'm full of crap? Well ok, this might be a little controversial but hear me out and let me tell you about my not so scientific research.

So there I was poking around my favorite free online dating site, PlentyofFish.com, when I stumble upon a little known component of the Plenty of Fish dating site. Buried in it's advertising section is a page in which you get a demographic breakdown of members based on the interests listed in peoples dating profiles. Yea I know, if you're a stats junkie like me this is a pretty sweet find.

Naturally, my curiosity got the best of me and I started plugging stuff in. For some reason the word "zombies" popped into my head and figured that was as good a place to start my search as any. This search brings up a whole statistical breakdown from gender, income ranges, education, marital status, height, body type and even drinking ability.

So lets see, people who are interested in zombies are mostly: males, making less than $25,000 a year, are big and tall/BBW, and drink more than 3 times a week. Awesome!

You might imagine how much fun you could have with this thing just plugging in random weird crap. For instance, did you know that people interested in necrophilia have a 300% divorce rate? Who would have thought that?!

Despite my juvenile usage of this neat Internet tool, I decided to put my mind to better use.

Recently I had an argument with a friend of mine which I declared that the overall population of vegetarian females was hotter than the overall population of omnivores. It was a heated debate and my friend being anti-vegetarian for some reason refused to believe my theory. In addition, I wrote a post a few weeks ago about how vegetarian dating should be one of the categories in which to filter potential dates by.

However, now I have a chance to somewhat prove my point. I did searches with the Plenty of Fish demographic tool for interests involving the words vegetarian and barbecue. I figured people don't write "omnivore" or "carnivore" in their interests section so I had to go with a more round about word, thinking that a majority of people who like "barbecue" are big meat eaters.

I plugged all the data from my searches into a nifty spreadsheet, made some graphs and this is what I got:

So as I suspected, a large majority of vegetarians are female, which shouldn't be much of surprise to anyone. Of course, men are all about the BBBQ's. For those Simpsons fans out there, you know what the extra "B" stands for.

The education level is certainly interesting, showing more vegetarians with higher levels of education. I'm not sure if this means that smart people are deciding to take better care of their bodies or whether eating a vegetarian diet makes you smarter. Either way there seems to be some correlation there.

Of course this was the graph I was most interested in. You see, I'm a bit of a drinker myself and it's important to me that I can drag my female dates out to my favorite watering holes with me. Even when I'm browsing chicks on the Plenty of Fish site, I tend to filter by drinking habits... is that wrong? Anyways, I'm a little disappointed to see that a large majority of the vegetarians on the site don't drink at all. Is there such a thing as being too healthy? Although, I suppose you could always use your date as a designated driver...

Last but not least, the characteristic that I'm sure most guys filter in their online dating searches is body type. Come on now, don't lie fellas, we know what's up. According to this chart, if you like thin, then you'll love dating vegetarian singles.

So there's your Online Dating Stats 101 course for the day.  That is all.

10 F*cked Up Online Dating Stories

Sure, plenty of people have found love on the Internet. Some find promiscuous flings. Some even end up getting married. This article isn't about those types of online dating stories. This is about those once in a life time circumstances, when the person you meet online turns out to be a compete disaster of an experience, you know, once that "real life" thing kicks in.

Without further ado, I present the 10 most F-ed up online dating stories you've ever heard.

1. Quasimodo Needs Lovin' Too

Bobby Finstock from the Pointless Banter blog has had plenty of adventures in the online dating realm and fortunately for us readers, they almost always end up in disaster.

In one of ole Bobby's finest intimate encounters, he provides us with his hilarious night with a girl/it that he dug up from the Adult Friend Finder site.

"When we got to the restaurant my “date” got of the car and walked liked Quasimodo half bent over. One of her legs was severely longer than the other, giving her a very interesting gait. We went into the restaurant and ate, while the conversation was good all I could think about was that she was freaking me out a little bit."

Read the Full Story

2. Your 7th Grade Teacher

So, there you are filtering through a bunch of skeevy emails from a bunch of skeevy dudes all thanks to a prank. This is what happens when your best friend decides to post a casual encounters ad for you on CraigsList. Well this exact story happened to one girl and what she found was pictures of her 7th grade middle school teacher in her inbox. Yea it was awkward when she called him out on it, but after he offered to send her MORE pictures, then it just turned out-right F'ed up!

3. So... What's Your Sign Again?

While perusing the Plenty of Fish forums (always interesting) I found this little gem of an online dating story:

"The saddest (therefore, worst since I find all women nice in some twisted way) was a woman who showed me her X-rays on the first date. And I offered to take her to the hospital the next day, and then to a doctor's office not far from the hospital. She had terminal cancer. I doubt if she is still alive. I suppose I was the last guy who treated her to Chinese take-out."

Yikes! Talk about a weird situation. Not that I'm making light of Cancer or anything, but man that's one hell of a first date to deal with.

4. Missed Connection or Just Missed?

This little tidbit I found on the You Suck at Craigslist blog, which is hilarious by the way. It's not exactly an Internet dating story, really more of an Internet dating fantasy. Because really, what's worse than a creepy guy sending messages on an online dating site than a creepy guy who fantasizes about dating then posts it online?

Read the blog post here.

5. The Handicapped Hater

E from Geek's Dream Girl shares one of her weirdest online dating stories. The guy is pretty normal at first but then he drops a prejudicial bomb on her. Nope, he's not racist, not homophobic, he's anti-handicapped.

"Now, I can understand hating racists, rude people, the willingly ignorant… but the handicapped have no choice in the matter. You choose to be racist. You choose to be willingly ignorant. You don’t choose to be an amputee."

Read the Full Story.

6. You Want Me to Drink What?!

Like the previous story, this guy turned out to be pretty normal at first, even offered to buy the gal a plane ticket to come visit him. Every thing went great on their dinner date, which eventually lead to kissing, and then to the bedroom. Unfortunately this is where things started to go downhill. Apparently the guy turned out to be a self-righteous douche-bag and the night ended with the following:

"Then he says, 'you know what, if you can do this little thing for me we will work out and you can have all the credit cards you want. DRINK MY PEE, baby.'"

Read the Full Story.

7. The Shark Attack Girl

The video speaks for itself.

8. Well, We're Not Blood Related...

So you meet a real nice girl online, you have great chats, she has a sparkling personality and for some weird reason you get along like you were family. Oh yea, did I mention neither of the two parties had pictures on their profiles... so you can imagine the awkward moment when you go out on your first date to meet your sister!

Now granted she was only his step sister but that's still a little weird, right? Well apparently she was into it!

Read the Full Story.

9. Would You Like Some HIV in Your Coffee?

This one is just truly scary. Imagine that you've found the love of your life through an online dating site. You are really sure she's THE one. You finally fly across the Atlantic to meet her when upon your arrival, you find out that the love of your life is really a level 9 psychotic bitch. Here's what this poor sap had to deal with:

"I found a note on the kitchen table saying that she wanted me out of her house and if I didn't get out by midday she was going to call the cops. This is even though I had been cleaning her dust infested apartment and looking after her daughter. Next to this note she had also left another note which horrified me. She claimed she was HIV positive and that she'd been putting her blood in my milk and food."

Read the Full Story

10. You Got the Right Stuff, Baby...

Jami from Date Wrecks has tons of ridiculous online dating stories but this one really takes the cake. Again, this guy starts out to be a completely normal nice guy in the beginning but by the end of the story you can't help but feel bad for how pathetic the guy is. Here is one text message she got from him after their third date:

“I want to turn into a metal monster and pierce you with a drill penis killing you and having to assimilate with me so we can be one.”

Wow, just wow!

As you might imagine, this sends up a major red flag. The worse part is that trying to get rid of the schmuck just makes things worse, to the point where he sings New Kids on the Block into her voice mail. The actual sound recording is in her post.

My summary isn't doing this any justice, just go read the full shit show right now.


If anyone can beat these 10 stories then please post your messed up online date in the comments or shoot me a link to the article.