I Ask Questions in My Online Dating Emails, But They Don’t Ask Questions Back.

Great info! I enjoy reading all of this blog, and it has stopped me from boggling my mind about a few things!

Anyway, I’m a male who is his 40’s on Match. I seem to run into this a lot and haven’t seen this addressed. In my first email, I usually ask a few questions and figure the female will answer them, which they usually do, but then they don’t ask anything of me but still seem interested. I may email again, saying, “If you want to know anything just ask”, etc. but I still get no questions in return to start a conversation. Confusing.

Should I assume this is one of those. “She isn’t into me things?”



Dear Dwayne,

It’s not that she’s not into you. It’s that you probably haven’t given her a compelling reason to be.

If you want to know why your email correspondence online is generally flat and falls apart after a few emails, you have to look in the mirror and take responsibility for your part in it.

Just today, I was on the phone with a client who was sharing the same experience with me: “Why do guys write such boring emails? Why don’t they ever ask questions? What am I supposed to say?” She showed me example after example in her inbox of generic email exchanges that have no fire, no wit, no flirtation. Yet she didn’t realize that she was an equal part of the problem.

It’s not that she’s not into you. It’s that you probably haven’t given her a compelling reason to be.

It wasn’t until she showed me one really GOOD email from a guy that she started to get it. He asked her a silly question and started grilling her with more and more trivia questions, teasing her about what she might win if she got all the questions right. She played along and pushed right back and they’ve already got a first date lined up.

I asked this client what made this email exchange different from the other exchanges.

“He was funny”, she said.

“And how did that make a difference to you?” I asked.

“It made me funny in response to him,” she replied. “He was so lively and engaging that I sort of had no choice but to come back with something equally witty and creative.”

“So by him writing something playful and interesting to you, he actually brought out a more playful and interesting side of you?”

“Exactly! What woman doesn’t love a funny guy?”

“You’re right,” I said. “And what man doesn’t love a funny woman?” She agreed, wholeheartedly.

“So if a man can make you into a more engaging person by writing a witty first email, wouldn’t it make sense that you could turn a man into a more engaging person by doing the same?”

“Yes, but it’s a lot easier when he says something and I can respond to him.”

“I agree. But look at the emails you write back to the boring men. They’re just as boring as the ones that you received. Wouldn’t it stand to reason that if you took the time to write something interesting and creative back to these guys, you might discover that they actually have a personality? I mean, from the majority of your emails, you sound really boring, too. And yet this one guy with the trivia questions was able to bring out your playful side.”

The moral of the story is that you are ALWAYS responsible for how you leave a conversation. This is equally true on dates. By being optimistic, playful, interested and interesting, you can almost always transform any evening into a pleasant experience. The problem is that we don’t; we expect the other person to do the heavy lifting – to make the plans, to ask the silly questions, to raise the playing field. We all want someone to set the tone and follow along, instead of realizing that we’re always setting the tone ourselves.

I realize that I’ve gone on a bit of a tangent from your original question, Dwayne, but this is important. If your email dialogue is flagging, it’s not simply because she’s not interested in you – it’s because you haven’t captured her imagination. You haven’t created a compelling reason why she should write back to you over all others. And yet most of us get online and wonder why it always feels so stale. It’s because YOU’RE making it stale, and you’re accepting stale conversation from others.

As explained in great detail in this article, most emails sound like they could have been pre-written by anyone in the world. Here is one short email that makes 11 mistakes in only a couple of lines. See if you are guilty of doing any of the following.

If you’re going to write the same exact email as every single person on the dating site, you can’t be surprised when you get deleted quickly like junkmail.

Dear X (1)

I just read your profile (2) and thought it was really great (3). I also thought you were cute (4) and loved the fact that you go hiking with your brothers every summer. I do the same with my best friends. (5). Anyway, check out my profile (6) and see if you like what you read (7). If you want to know anything more about me, just ask. (8) My number is 555-1212. (9)

I hope to hear back from you soon (10).


Here’s what’s wrong with this very simple, innocuous email that you’ve probably written (or received) 100 times.

1) Dear X

She knows her name. Better to start off with something engaging right from the get go.

2) I just read your profile – She knows you read her profile.

3) …and thought it was really great. Of course. Otherwise, why would you be writing to her?

4) I also thought you were cute. She knows you think she’s attractive. So does every other guy on here.

5) and love the fact that you go hiking with your brothers every summer. I do the same with my best friends. “Me, too!” The crux of most email exchanges is taking something the other person did and saying, “Me, too”! There’s nothing wrong with a “Me, too” email, but how is someone supposed to respond? “Um, great?” Establishing commonality is often a symbol of trying too hard to sell yourself.

6) Anyway, check out my profile. She knows she’s supposed to check out your profile. That’s usually what happens after someone reads an email.

7) …and see if you like what you read sounds weak, like you’re asking for her approval. Assume success and you’re more likely to have success. Say “if you like what you read” and you’ll probably fail.

8 ) If you want to know anything more about me, just ask. Your profile should be good enough that she shouldn’t have to strain hard for information about you.

9) My number is 555-1212. Newsflash: Women don’t like cold-calling strange men who offer their numbers on the Internet!

10) I hope to hear back from you soon Wishy-washy. Don’t put her up on a pedestal.

11) Sign your name! You sound creepy if you don’t warm it up with a signature.

This probably sounds incredibly nitpicky, but it’s not. If you’re going to write the same exact email as every single person on the dating site, you can’t be surprised when you get deleted quickly like junkmail.

So if everything you’ve been doing in your emails is ineffective – if everything that comes naturally to you is too dull – what ARE you to do? The opposite of what’s above. Don’t say anything that is obvious. Don’t sell yourself. Don’t kiss ass. Don’t overpraise. Don’t ask for them to consider you. Don’t ask for them to write back to you. Act like you’re a catch – confident, bold, funny. If you sound like you’re presuming you’ll get an email back, you’re much more likely to get an email back.

And remember, keep it light. You’re not here to find out if a person will sleep with you or marry you in a first email. Could you imagine having such serious conversations with a stranger at a party?

“Excuse me, ma’am. You look very attractive. I think we have a lot in common – particularly our mutual love of rum punch. Would you like my phone number and to learn more about me?”

Who would a woman rather go out with – the boring lunkhead who asks for her number before he’s had a chance to charm her, or the witty guy whose every email she anticipates with delight? It’s a no-brainer.

Imagine saying that in real life! Now, consider that you’ve been saying that to hundreds of women online for years. No wonder the conversation goes nowhere!

Whether you’re a man or a woman, you need to differentiate yourself. And studies show that confidence and humor are the two most desirable qualities in both men AND women. So instead of playing the blame game and pointing fingers at people who take a long time to email, or say nothing interesting, or write only one line, step up and try a little harder yourself. You may be shocked how those same people become a lot more interested and interesting when you give them more to work with.

I’ve got two techniques for writing first emails that I describe in Finding the One Online. One is called Fun Fiction, in which you make up something silly based on a detail in the other person’s profile. The other is called Opinion Openers, where, instead of stating a “me, too” fact (You like Bruce Springsteen? I like Bruce Springsteen!), you offer your opinion – in which your personality shines through (Hey, if The Boss is from New Jersey, how come he sounds more like Woody Guthrie than Tony Soprano when he sings? What part of New Jersey has an Oklahoma accent?).

You may think that this stuff doesn’t matter – that people only write back to the most attractive people no matter what. So while I will acknowledge that being hot and stupid is more effective than being ugly and fascinating, the truth lies somewhere in between. A great email will never make someone who doesn’t want to date you consider you, but it WILL tip the balance when someone is choosing between a dozen otherwise similar candidates. Who would a woman rather go out with – the boring lunkhead who asks for her number before he’s had a chance to charm her, or the witty guy whose every email she anticipates with delight? It’s a no-brainer.

So do yourself a favor, Dwayne: stop beating up on yourself because she doesn’t sound interested. Be more interesting, and you’ll never have to wonder if there was anything else that you could do on your own behalf.

Seriously, my friend, this is a very do-able technique and I’ve helped hundreds of guys (and thousands of women) master online communication.

Check out my CD series if you really want to get the best results out of your online dating experience.

And don’t forget to let me know how it goes…

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  1. 31
    Karl R

    hunter asked: (#29)
    “Karl, don’t you get winded while dancing, making it difficult to chat at the same time?”

    That’s generally not a problem, but it can be an issue with certain styles of dancing and speeds of music.

    “I have heard, some men can multi-task, mostly, the left handed ones.”

    I’m right-handed. I’m not sure if left-handed men find it easier to lead (which requires multi-tasking, even if you’re not talking) than right-handed men.

  2. 32

    Also, if it’s a stationary dance, all you gotta do is be thinking about the next thing you’re gonna lead. If it’s a moving dance, you gotta also worry about navigation.

  3. 33


    I also have had experiences with men going on at length about a topic I asked about not at all. This is where some women can get silent. If you wonder why your date is silent, wonder if you’re monopolizing the conversation, or turning it back to you, constantly. Not in every case, of course, but…does it for me!


  4. 34

    Try to make sure you’re asking a lot of questions, and NEVER talk over someone.

    casualencounters.com/blog´s last blog post…Casual Encounters Web TV Show, Episode 4

  5. 35

    I have been contacted by witty guys, and that got us started. It doesn’t guarentee that it will be a good match in the long run, but it does help get things off the ground.

  6. 36

    Ask ladies fun open ended questions and also hypothetical situation questions. Also think of some that you can ask when going on dates so you don’t get stuck on the date and can pull them out when you don’t know what else to say. Some questions that come to mind for example: If you won an all expense paid trip for two weeks, where would you go?,  also What are her favorite movies?, what are her favorite movies of all time?, What’s her favorite restaurants? etc etc…. You get where I’m going with this? It’s open ended questions but not only open ended questions but fun interesting questions that make people think about the questions and engages them into the email. Another possible question could be something like if you were or could be a plant, or a tree what kind would you be and why? They may seem corney to you but they are at least interesting and getting her to see that you are fun and you have interesting questions to ask rather than the hum dum same ol boring question. Don’t just ask about family or questions that just have a yes or no answer those are boring.    

  7. 37

    Also by asking questions like I have given examples it allows her to think about the questions, respond and then she will want to know your answers to your questions and she’ll most likely then have questions for you that she is thinking of while she answers your questions.

  8. 38

    Email is ambiguous. I have read through women’s profiles, come up with something really humorous and original to say and shot off emails with a smile on my face…only to have women lash back with fury after completely misunderstanding what I had said in my email. I know what I said was humorous as I have used similar wording in person at, say, house parties and got very good, flirtatious responses and the occasional wry face. So trying to be humorous online is a big hit or miss as there is no tone to your email and no sense of chemistry. I have noticed that it’s usually women in the 35 to 40 age group (I am 38), white and well-educated who have responded like that.
    Today, I keep my emails brief, contact only those in the 30 to 35 age group, generally won’t write to scientists, professors, very technical women or anyone with a penchant for arguments like lawyers and try to take things offline at the earliest. This screening is good in other ways too since I figure it takes 5 to 10 minutes for me to read a profile and come up with something so say. When you sit down and write to six women, that comes to an hour. That is valuable time!! I also don’t text women in the earliest phases of dating except to schedule a date.

  9. 39

    So what? Guys are supposed to be fucking clowns and entertain the women on dating sites? This is the problem right there. Ladies, men aren’t here to provide you amusement. We aren’t your jesters, so stop treating us this way. For some reason women on online dating sites don’t think they have to give any effort or be interesting just because they possess a cagina. If you are on a dating site and are responding to a guy that generally means you are interested. If that’s the case act like it and do your part.

    1. 39.1

      Sometimes it’s not what we say but how we say it.

  10. 40

    When it come to love, romance and sharing a connection, it all about timing. You don’t want every person you may feel interest you! If you are a beautiful person inside out, trust me, someone will want you. So many people now days have many personal problems that enable them from make a genuine connection with someone. Stay positive, the right he or she will show up ready to love you!

  11. 41

    Yes, of course. If the woman doesn’t ask any questions, but replies anyway, it must be the man’s fault. Clearly, you are compelling enough for her to write back, but not compelling enough to answer a question. It’s clearly your fault and it couldn’t possibly be a social deficiency on the part of the woman. 

  12. 42

    The right time is always now! Because we all change, our inner world alters, and thus our preferences change too. And “Mr. Right” need to change day to day, inside himself. In other words, we should develop, long for more, open new horizons. And the right person should do the same. Together we’re powerful and happy. Many people find soul-mates at http://kovla.com Try it, maybe your destiny is waiting! Good luck!

  13. 43

    I also get a lot of messages from men, and my least favorite is “how are you?” I hate that question, even in verbal conversation, unless I really haven’t seen someone in a while, and then I want to know how my friend is doing! With that said, I have tried to engage these guys in conversation, and they simply don’t have anything to say. In fact, I got an email from a guy today. The guy is cute, and I really do want to engage him, but I don’t feel it’s worth the time and effort because all he did was say “hi how are you?” I’m afraid he’ll be just like the others who started off the same way. It’s painful trying to move the conversation along with guys like this. And, they never ask you out!

  14. 44

    So the advice boils down to ‘be funny’? Well thanks for that I’ll just fire up the ol’ witty charm machine right now… Oh wait, that was something I made up, silly me.

    What utterly junk advice. Be funny, just like that eh? Pfft.

  15. 45

    Let me be blunt with the men here.  The women that do get a ton of emails, and I am speaking from experience are going to focus on a few basic things, first and foremost your picture.  Please post a good one.    As someone else commented I have a full time job and it is not online dating so I am trying to get through 40 profiles a day I am going to mostly look at the picture, if its bad, I am going to move on.  Certainly guys cannot control if a woman is going to be attracted to them or not, but they can control putting a good picture up.  Ask some female friends for help.    If I look at the picture and I do not find you attractive it does not matter what you said, how witty it is etc, I am not going to respond.  I am sorry those are just the breaks. I email lots of guys who don’t respond to me either.  Second, I look to see do you meet the basic requirements that I have written in my profile, meaning have you actually read it, which 90% of men do not.  If you clearly have not I am not going to respond.     If you meet both of this criteria and don’t say something dumb I will respond even if is just a hi you sent.      I get men who are 10 years older than I am asking to date, who smoke, who live ten states away, etc.  No I am not going to respond to these men.

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