Anatomy of an Online Dating Email Conversation

Posted by in dating after divorce, online dating after 40, single women over 40 | 3 comments


The following is an actual conversation that took place between my client, Jane, and George, a man she met on JDate. What started out as ‘possibility’ turned confusing and frustrating very quickly. I am displaying this conversation for your edification. Many clients want to know how to email a man online. This conversation illustrates how to get clear very quickly about whether a man is right for you. I have inserted my opinions in parenthesis { }.

George: I enjoyed reading your profile and (now for the superficial part) you are also attractive. {Men are so focused on women’s looks. And they’re usually pretty open about it} I know we are not exactly “neighbors” {he lives about 9 hours drive from Jane} but for me it is much more important the “who”, and the “where” can be worked out. One of my favorite quotes: “If you think you can, you may … if you think you can’t, you’re right”. I think I can … how about you 🙂 ?

Maybe you would take a look at my profile and let me know what you think ? Hope to hear from you soon …

{note: Don’t ask someone to look at your profile. If they’re interested in your email, they’ll check you out. Asking them to look at your profile connotes a sense of neediness}


Jane: I like that quote. It describes one of my life philosophies. It’s hard to know much about you from your profile, as you say very little. I would be open to finding out more…

You write that you’re a ‘Traditional’ Jew. Can you describe what your Judaism means to you and how it plays a role in your life today? {Jane is trying to find out more about George’s commitment to Judaism, as that’s very important to her vision for an ideal mate}


George: Thanks for the nice response. Rather than tell you what Judaism means to me, I think I will tell you what I have done over the past number of years.


{Here, George goes into great detail about his work on different committees through his synagogue and other Jewish organizations.}

I hope that gives some idea of what I am about. Let me know what you would like me to amplify on. Have a nice evening !!!


Jane: You are definitely committed to community development! I am impressed by your devotion and willingness to serve the community/congregation.

I, too, am very involved in my synagogue. I have served on several committees, most recently the ritual committee for a few years. I enjoy giving back, as it appears that you do, too.

It says in your profile that you are retired. What do you do with your days now? Why retire so young?  {He’s 58}


George: As to being “retired”, I worked in my family business. I sold the business a number of years ago and that pretty much makes me retired. Not from the world but just from the 10 hour a day, 6 day a week minimum world. I watch some investments and, as I mentioned, have done quite a bit of volunteer work in the past years. In my spare time, I lay on the couch eating bon bons watching soap operas … just joking 🙂 LOL … hope that made you smile a little.

{Jane didn’t really find this funny, but she went with it on her next email. The bon bons are kind of a lame reference, very outdated, and a bit concerning. Maybe he really does sit on the couch a lot.}


Jane: Your life sounds like it’s been interesting. The bon bons sound delicious. What’s your favorite soap opera? I want to hear all about how Jane Doe had amnesia and killed her uncle’s second cousin Harry, with whom she had a son three years earlier…  {Humor is a great way to connect via email when you’re first establishing a relationship}

Anything you want to know about me? {notice that George has asked nothing of Jane during this entire exchange, and it’s beginning to concern her. Is he self-consumed? This is important information in determining whether he is a good candidate for a relationship.}


George: I have what some people feel is a somewhat annoying approach to asking questions and that is … I don’t. I understand, though, someone else’s “need to know” and have no problem responding to any sincere inquiry [like yours :-)]. My feeling is that if we don’t meet at some point then I really don’t need to know anything. If we do meet and think there is some mutual interest then all will be revealed in due course 🙂 But if there is something you would like to share, I would be happy to listen or read in this case :-).  {Huh? ‘I don’t ask questions? If we don’t meet, I don’t need to know anything?’ Why did you start this conversation in the first place, George? And enough with the smiley faces!}


Jane: Your last email has me scratching my head in confusion. If you don’t ask questions, you can’t really get to know someone. I am not asking deep dark probing questions, simply questions that would reveal some of your values and help determine if we want to take this conversation to a phone call and possibly an in-person meeting some day.

And here’s the confusing part: your first email said “I know we are not exactly “neighbors” but for me it is much more important the “who” and the “where” can be worked out.”

My understanding was that you were interested in exploring whether there was potential between the two of us, and I took the bait because you seemed like a good guy.

If you are not interested in furthering this conversation by asking questions, that’s okay. But I am not interested in a one-way conversation. {Jane is clear. She’s not interested in playing games or continuing a conversation that’s one-sided.}

Best of luck to you.


George: It seems to me that people on JDate get a little too wound up with information. {What does this even mean?}If you met me at a charity event or the like and accepted an invitation to dinner, you would know less about me in those circumstances than right now. I am not one to make an inquisition of questions back and forth. {Who’s calling this conversation an inquisition?} That is just the way I feel. I would rather meet someone and have a conversation. If you don’t have courage or just the inclination for that, I perfectly understand.


Have a nice evening.


Jane: Courage? I was trying to get to know you. I don’t enjoy one-way conversations. I don’t enjoy being cryptic. And I am dating to find love. I am not lacking in courage,George. I responded to your first email because I was willing to take a leap and see where it took us.

Best of luck to you.


George: Thanks for your thoughts.


So, there you have it. A conversation that took a nose-dive because of some wrong turns. If you’re looking for love, it’s important to be focused on what you want and be able to sift through the men who are merely detours on your path to love.

I’d love to hear your thoughts on this conversation and whether you agree or disagree with my notes.

Happy dating!




  1. I don’t think it was a matter of what George said and that he could have done things differetly. A jerk is a jerk. At least is was an honest exchange and they didn’t waste any more time than necessary figuring they are not compatible.

  2. It just looks like a bad fit to me. He attempted humor and you, Sandy, didn’t appreciate it, while Jane at least got it and went with it. I’ve found humor is a great way to find out if there is a connection. If she doesn’t get my jokes, then we can just move on.
    That said, I’m not sure who a good fit for this guy would be. Not sure he is a jerk, but he is definitely a bit odd. He is definitely not as interesting, deep, or Jewishly committed as Jane is, and that coupled with the total disconnect makes it pretty clear furthering the conversation is a waste of time.

  3. Joshua,

    I agree that humor is a great way to connect, and if you saw my note, that’s what I said. Jane didn’t find George’s humor too funny, but she went with it anyway, because she has been coached by me to use humor in her emails.

    I also wouldn’t label him a jerk like the other contributor. A bit odd is a better description. Not a good fit for Jane for sure, like you said.

    I posted the conversation for a few reasons.

    1. To demonstrate that you can usually know whether you want to further the relationship after only a few emails are exchanged.

    2. To encourage people who are dating for a serious relationship to not waste time on people who are not a good fit. Why expound the energy when there is an obvious disconnect?

    Having said that, I encourage daters to be open and not jump to conclusions when there are lots of compatibility factors present.

    For example, just because someone has typos in his or her profile doesn’t mean they are illiterate.

    Just because someone doesn’t have a degree doesn’t mean they are not smart.

    You get the point.

    Thanks for your comments.

Leave a Comment

Your email address will not be published. Required fields are marked *

AlphaOmega Captcha Classica  –  Enter Security Code

This site uses Akismet to reduce spam. Learn how your comment data is processed.