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.


  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. Anonymous8:56 AM

    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. You really have a good blog going!
    Will be back soon to follow up.

  5. Nice work. Yeah, it's definitely good to build a conversation around specific topics (I call them "conversation nuggets," link on my name above. It's like the improv game "yes and" where you build upon what your partner says. It's like a snowball. You have to start with a little snow, and then it builds up as you roll it.

    I agree with TheGirl that many women are willing to meet after just a few messages. I personally have had more success being very specific about time, date, and venue when asking a girl on a date, too. It makes it much easier for them to say "yes" because they know exactly what's involved. Any ambiguity can get you easily lost in the shuffle - though building a good conversation is great protection against that.

  6. Hey Matthew, as a dating coach who teaches lots of students about being successful with online dating, I'd like to add my two cents here.

    First off, YES... you're absolutely right: banter and asking questions work really, really well because it leads to spontaneous, fun conversations that create a whole lot of attraction.

    And I've got one more email tip to share here: pay attention to the subject of your email.

    Even if you have the greatest message in the world to send to a woman, you won't get a response if she doesn't click on the subject of the email. It works just like Hotmail and Gmail do: people see the SUBJECT of an email BEFORE they see the actual message...

    And in a world where women get dozens of messages per day on most dating sites, making sure your email subject stands out becomes rpetty damn important!

    Now, 9 out of 10 times men won't use a subject at all, or say something along the lines of "Hi", "Hey", "hello", and "you're pretty" kind of things in their subject. Your job: bring the banter here too.

    If you're going to tease her about being a movie junkie in your message anyway, simply use an email subject like "Heyyy... movie junkie!" It will immediately grab a woman's attention because it's about HER and her alone. It's not something you would say to every single woman, so it grabs her attention and gets your message opened = getting more responses!

    Try it some time...

    To More Dating Success,

    Dennis Miedema
    Win With Women

  7. Anonymous5:05 AM

    Did you make that up yourself or somebody write it for you?

  8. Lol! What's with you being anonymous?

    Kinda lame to imply somebody made a blog post up without signing off with your name. Talk the walk and walk the walk man.

    Although I don't agree with everything Matthew said, at least he has the guts to be open about it :-)

    To More Dating Success,

    Dennis Miedema
    Win With Women

  9. 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.

  10. Not only does your article about email as an effective way to communicate while online dating, the comments here are just as helpful as well! From now on, I will totally pay more attention to my email subjects. haha! :)

  11. Anonymous8:48 PM

    My question would be, whether the relationship ever got off the ground. Did she ever answer her phone? lol The more attractive and desireable a woman is, the less likely she will be to be dating on-line! I really do think, many attractive women are on POF just to keep an eye out for that cute plastic surgeon! And when HE does contact her, she could care less about what he does or doesn't say!

    In fact, although I considered myself successful on POF for having had a one year relationship come out of it, I realized that like so many women, this one contacted me, enthusiastically, simply because she WANTED something and it wasn't REALLY me!

  12. Anonymous10:58 AM

    I really don't get any of this, why bother with all the email in the first place? I just post in my profile I want to skip all that, if you have interest based on the profile, then just go straight to the meeting in person. Emailing banter is a waste of time, do the banter in PERSON! Seriously, what is the point of doing that in email when you could be finding out in person if you even have any interest for REAL?

  13. Anonymous2:45 PM

    You did quite well with those emails.
    BUT I kept thinking.. she's not asking YOU anything. She's answering.. okay that's good.. but she's only talking about herself. You pretty much had to carry the conversation. That would turn me off.
    But.. kudos anyway, for getting her phone number! Maybe by phone she's more curious about you and not just answering about herself.


  14. These are some great tips. I'm on POF and also use Craigslist to successfully meet lots of women. Banter is important either do it through email or my personal favorite text messaging. I've written about some of this in my ebook called The Slacker's Method: Guide to online dating. It wasn't until I started slacking that I got successful so thats why I called it that. Anyways check it out.

  15. Anonymous2:53 PM

    Yeah, it worked... in 7 messages. I mean, granted, I use POF to rope girls into getting played. So, I'm not really trying to reassure that the girl I'm about to date is my intellectual equal. I'm not trying to marry these girls, I'm just trying to get someone to play with my ding-dong. I've dated some girls from POF that are uninteresting, self-centered, and down-right BORING, but a little patience goes a long way. It's all about the play. I've told girls I'm a Democrat, a Republican, an Atheist, a Christian... just about anything it takes to get them in the sack. If I send 10 messages, I'll usually get about 6 replies. On 4-5 of them, I can usually close on a phone number or MSN addy within 4 messages. And, you don't even really have to prey on fat ugly girls. I've slept with 5 women so far this year, and none of them weighed in over 170.

  16. Anonymous11:09 AM

    ...And you think the girls are self-centred and uninteresting? The good thing is that most guys like you don't realise how transparent their motives are.

    That's why guys like Matthew and Russ shine. Robin showed a good level of insight too. These are the types of guys worth finding on a site like PoF.

  17. Anonymous5:21 PM

    LOL, how very funny that this guy thinks he is the only one using someone...Often times when I meet a guy from a dating site, and he's attractive but not my type, I will have sex with him because I WANT to, but I have no intention of seeing him again. Here is a clue guys, if she DOESN'T sleep with you right away, it usually means one of two things: She likes you and knows she has to play the stupid man game of not having sex with you or you will think she is a slut, or she doesn't have any interest in you at all. You will know which is which if you are even halfway smart.

  18. Anonymous9:54 AM

    I get my dates in one, I say online dating is full of shit....lets get coffee...they laugh and it works! But first I say Im from the other galaxy.. another laugh try it......with a simple to the point profile,,,no bull interests and honesty

  19. Anonymous8:04 AM

    Gee, thanks guys! After reading your insightful informative blogs, I think I've changed my mind about trying online dating on POF after all! :)

    Nice girl

  20. Anonymous4:45 AM

    reading thru your blogs..it seems to me that mostly to everyone its some sort of game to see how quick you can score. Whatever happened to taking ones time and seeing if you have common ground...its not about seeing how many times you can jump into bed...for some of us its trying to find the right partner to enjoy life with.With some there is a matter of distance to consider, while personally I wouldn't be contacting someone overseas, a distance of 500 or so km is workable. However for me to be willing to travel that distance, I would like to get to know my prospective partner via emails and phone conversations before I embark on such a trip. Some of us are hitting our late 40's or early 50's and I for one don't have the time nor the patience to play inane games that lead to a romp in bed, I can get that anywhere. Also if one is going to use a bit of logic..one may realize that people born in the same decade, usually have the same taste in music, styles of living, food etc..there is the odd exception, so finding things in common is a relative breeze, if one is short on what sort of questions to ask...there are many websites that give you these, the point of all this...if you make each other comfortable, you will take it further and contact each other..if not then you're probably with the wrong person. I still think its a lot easier meeting someone thru clubs or just being out and about..but dating sites have the advantage that you already know that some people on those sites are looking for the same thing you are...

  21. Anonymous3:03 AM

    Hey everyone! It is my first time in a dating blog, so I am not much aware about the concept here. I think this may help me sort out my issues that I am having trouble with. The Blog is doing an excellent work for people like us

  22. Anonymous4:38 AM

    Well its quite alarming that alot of the population still rely on the internet to find our true love instead of the real life situations.
    I have been on and off with guys on pof and all id like to point out to guys who read this that questions included in conversations is alot better than just keeping dull and not a hint of creativity

  23. Anonymous3:49 PM

    One piece of advice to guys that I would add is that if the GIRL signs her email with her name, you need to sign yours with your name too. It's called the rule of reciprocity and is one of those non-verbal signals that you "want to dance". And I totally agree with the snowball conversation thing too. Take what she says and see how much you can get from it.

    Oh, and if you banter too much (7 emails is a LOT), then she may get bored or think you are a scaredy cat or don't want to meet in person for other reasons (don't look like your pics, are already in a relationship, etc.) so I'd try to close the deal sooner.

    Last suggestion, don't wait for her to just hand you her email or IM ID or phone number on a silver platter, ASK for it. I've only not given my number to a few guys who asked and these were the reasons:
    1) I wasn't interested in them
    2) One of them completely ignored my request to IM first and just kept repeating over and over and over again "what's your number? Here is mine". If a guy doesn't listen to me in our first email interactions, chances are he is not going to listen to me while we are dating either.

    Happy hunting!

  24. Anonymous11:39 PM

    I agree with Anonymous. A couple of flirty banters is great, but after that, get to the meat and potatoes.

    I'm on POF and I have lots of commentary. But, to be brief, guys, if she does give you her name, USE IT. Matthew, if that is your real name, you did a very good job of that. Also, and this is just me, please capitalize, punctuate, and at least make a stab at proper spelling. This is a pet peeve of mine, but I'm sure there are a lot of smart women out there who are immediately put off by this type of thing; i.e. "thanks for gettin back to me LOL so what do you like to do" Oh, puh-leeze.


  25. Anonymous8:57 PM

    I just wanted to comment on the one lady's comment regarding playing stupid man games or just sex with guys......
    Yes, you are right.

    But I know hen I've set the hook so to speak. I know when you really like me. That's when I know I have a fish on and whether I'm going to take it home and mount it or drag behind the boat as chum for something better......

    A guy with options scares many of today's women. They are so used to control by anatomy(you get the idea) that when a man has more than one to choose from (and the woman really likes you, but can't control you) she loses much of her power.
    Now if she has quality traits as well, she'll keep a guy. But if a golden piece is all she's got, well even gold tarnishes.

    Rod Evans

  26. Anonymous5:38 PM


    OMG....some of these comments are very disturbing. I really think that around 2% of the guys on this website are genuinely nice guys looking for a partner. The others are just sad people who, one day, are gonna wake up old and alone. I thought about going back on this site but remember what complete wackos are on here. I am glad I stumbled across this. I would rather be single than be prey to these utterly egotistical arsewipes. Even the ugly ones are arsewipes. What is all that about? Listen gals, if you were thinking of going on here. Don't!

    1. > I really think that around 2% of the guys on this website are genuinely nice guys looking for a partner.

      Yes, and as long as you (and other women) think that (without and evidence to back it up), nothing will get any better.

      You couldn't be more wrong, the real numbers are: 75-85% of the men are "genuinely nice guys looking for a partner" -- but after 5 years of the you-know-what that women drag those men through on the sites, they get angry.

      THEN, you women pretend like you're never frustrated or annoyed or cuss.

      You're unrealistic and hypocritical.

  27. Anonymous7:27 PM

    sounds like Karen needs to get some...


Comment Policy:

Comments posted on this blog are moderated and will be approved only if they are on-topic and non-hostile.

Avoid including website URLs in your comment body and instead place them in the URL box in the comment form. Though Anonymous posting is enabled, please use a first name (even if it's fake) so that it is easier to identify commentators when responding to them.

Thank You.