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 emails and messages from where else but the PlentyofFish dating site.

14 thoughts on “Sample Online Dating Email Messages

  1. Hey, I'm impressed by the tactics. Email analysis and response is one of those skills that you never know you have til you're staring down the barrel of a dating website…
    Still, I've generally found that people are often ready for you to suggest a date a lot sooner than you think – sooner even than seven dates. After all, you're never going to find out if you fancy someone til you meet them – so if you like their profile, and their first email, you might as well suggest a meet up pretty soon after. It's the only way you'll know…

  2. I'm on POF and am amazed by how many men never ask any questions. Last guy I went out with from there (3 months) proved to be self obsessed and I remember it took him SIX messages to ask me a question, lol. Lesson well and truly learned! Don't always trust what they say in their profile, judge from their behaviour and you will do well.

  3. some good tips there, I've used online dating for a while and know first hand that the more effort you put into your chatting up in initial emails there better the chances there are for having a date agreed. It's not always that simple though – there are times when the women are very forward and will suggest a date out of the blue. It's all down to having a good selection of pics and catchy / interesting profile in my opinion.

  4. I noticed that your site is mostly about POF and I was wondering if you did profile critiques? I have one that gets alot of responses for its uniqueness, but doesn’t really ‘hook’ anyone. I was asking if you’d take a look.

  5. i ask stupid questions to the ladies every message. i think that it is important to carry on with the conversation. if you just go on about shit ya bore em and they stop responding. Just ask a stupid question about anything and the responses are usually good!

  6. this article was very informative. I have also noticed that direct compliments are cheesy, and they dont respond. I like that you insulted jane humurously, just because she was probably used to non stop compliments, and then was critiqued on something that was actually something that she was fully interested in.

  7. I don’t know about this, I think he had it much easier. 90% of girls do not send a first message. I mean he does a really good job at responding but she was quite sold at 1st message (he says his profile was very interesting and great). So I’d like to see him start a conversation 1st rather than get one. It is a lot more challenging that way.

  8. Don’t you think you messaged back and forth waaaaaay too much?

    She showed a lot of interest by contacting you, it’s rare for a girl to make the first contact. You could have asked for her number with you’re 1st response, 2nd response tops.

    What’s the purpose of so many emails?

    -Radio Wright

  9. hi i were dating a german girl on facebook and we were progressing ! but i didn’t tell her any thing about what i feel but i told her that i like her and she said no probs ,thena few days ago she didn’t write to me !? so what should i do?? help please i don’t wanna loose her!!!

  10. @ R A Z O R S H:

    It could be that she is just busy.
    OR, because you made a “confession.”
    She lost interest. Why?
    Because she knows she has you, therefore, there is no need to pursue you anymore.

    What it comes to is you are either beta, or alpha.
    We were raised to be beta.
    We need to learn to be alpha.

    Research “David DeAngelo” on youtube.

  11. I’ve read all of the advice and I’ve thought about everything said. I think that dating on POF is too complex. Does it reallt take all that to make a match? I think if a woman is interested, then it wouldn’t take much for a match to be created. It sounds like this website is set up to bend over backwards for women and I think that alone places women on this site on a pedestal like their the cream of the crop. Why should I go through a ll of that trouble for women who aren’t even interested in finding anyone good? They just like the attention. Quality women can READ emails and separate the good guys from the bad. We know that most women these days don’t like good men…they may seem boring, but ask a battered and abused woman how exciting it is to deal with a “bad boy”. This site is a waste of time. If you want to have a better chance of find a QUALITY woman, get on a paid site. Nobodys going to waste money to pat their ego’s online. plenty of fish for sure, BUT no QUALITY. I will take quality over quantity any day.

  12. bt we didnt even dispute i dont know why she changed and i sent to her a happy neew year message and she didn’t reply bt she answewred only one word”thanks”

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