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…

Join our conversation (66 Comments).
Click Here To Leave Your Comment Below.


  1. 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.  

  2. 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!

  3. 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!

  4. 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.

  5. 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.

  6. 46

    This issue drove me bonkers when I was online dating and I don’t think I was the common denominator since it was sporadic.   I would do my best to ask personalized questions based on their profile and they would make the effort to respond to my questions without asking me any questions or giving me something to write back about.   I would give them the benefit of the doubt and send off another message but would get the drivel back.   Sometimes I would get mad and let them know how off-putting their lack of effort was (and they would tell me off- ok, fine, it wasn’t going to happen anyway…).   Now I know better and to just move on (although I met a really great lady and I hope never to have to be OLD again.)

  7. 47

    I have experienced this too: a person who replies but does not ask you any questions. I get that our messages must be interesting and funny but most of us do give an honest effort when writing a message to a person  we are really interested in.    So if we are making the effort but this person for some reason isn’t responsive and isn’t willing put some effort of her own  into the process, then I think at some point, we must just reach the conclusion that this person is decisively not for us.   I mean if she is not doing her part then it means: 1) she’s just so-so about you; maybe she’s just keeping you  as a lifeboat, while interacting with other candidates who she feels are more “important”; 2) she is boring, passive or, even dim witted, who can’t or is too lazy to write anything interesting; would you want  to be involved in a serious relationship with such person? Probably not; 3) she is shy; there is hope here but if after a dozen exchanges, you don’t feel any improvement, then clearly it is not shyness; 4) she’s a  diva; in which case, she expects the man to do everything for her.   But there is hope here too.   We all know some women likes to play hard to get but usually,  as time goes by, she becomes less “diva-ish”.   So it’s really playing it by ear in this situation.

    As for the importance of being funny, when I hear this, I always reminisce about the movie “Gone Girl”. During the courtship phase, Nick was charming and funny.    But behind  this facade, he’s an unfaithful, weak spirited, and even stupid, husband.   Funny is overrated.   But I get it.   In this day and age, patience and subtlety have become abstract concepts that few people understand, let alone appreciate.   Therefore, it is natural to see humour and charm gain importance.   We have no time for subtleties, no patience for the depth of a person’s personality to reveal itself.   We want to know (at least, we want to believe we know), to enjoy and to be entertained right here, right now.   (We are brainwashed by movies into thinking real dating is like in movies.)   If this is the demand in the dating market, then the supply is usually the confident-looking, perhaps narcissistic and often very entertaining I must admit,  extroverts.   I find Li-Ann’s comment about self-focused personalities very apropos.   Our modern society is tailored for these people. Humility has no place.   In the times when  our grandparents and ancestors lived in small towns, everyone knows everyone.   There was no need for you  to advertise yourself, to boast or to entertain a facade because everyone knows what you’re about and where you came from (and they know your parents and your grandparents).    But now, the majority of people live in gigantic cities where no one really knows anyone, so to speak.   Thus, the importance of advertising yourself; the importance of constantly talking about yourself, about what you’ve accomplished, where you’ve been,  what you’ve bought, etc.   With the advent of social network, it has become even worse — everyone is pretty, everyone eat wonderful meals, everyone has beautiful  trips all the time, etc.   But who are we kidding?

    All this to say that it is sad that this social behaviour that is dating has been reduced to browsing profiles consisting of  a few pictures and a little paragraph.    And then, when we find someone that looks (the pictures) good enough for us, we judge them by the few messages that they write.   The world has never been so superficial, and impatient.   I know some women who  are really beautiful in person, by the confidence emanating from their postures and movement, by the intelligence from their  gaze; but whom pictures do not do them justice.   I know men who are serious by nature but who are also very interesting (in conservations where you can actually learn something new, not just mindless small talk), thoughtful, sensitive and reliable.   Could these qualities that most women, I am sure, appreciate naturally reveal themselves after just a few messages?   Likely not.   So while humour is good to have, I think smart women (and men) online-dating should widen their internal filters and stretch their patience a bit.

    1. 47.1

      Hi DSL. I fond your response incredibly intelligent and thought-provoking. I agree with you about the narcissism and superficiality of the society that we live in. Gone are the days of subtlety and depth. Or if those people do exist, it has become impossible to locate them. I would love to communicate with you further, but I don’t know if this reply will find you. If it does, please respond, and maybe we can exchange emails. I would love to have a friend who thinks as deeply as you do.

  8. 48

    This advise is simply terrible.   There is absolutely nothing wrong with the email you are using as an example.   If I like the guy’s profile,   I would have not problem replying to this email.   It is honest and straightforward.   Much better than a cheesy email any time of the day!

  9. 49

    I completely agree. I’m MUCH more likely to respond to someone who writes something funny and witty, than some random, generic message, compliments or any kind of “well the ball’s in your court now” type statement (like, here’s my number, read my profile, ask me any questions etc). I’ve also changed my approach, in that I used to write quite serious, heartfelt messages at the outset, now I write really short, funny, quirky type messages referring to something in their profile. 95% of the time I’ll get a response. A funny personalised message just begs you to respond. You almost can’t help it!

    The only problem I find is that I can’t keep up that level of banter and fun. I find it easy to put it in writing, particularly as a first message, but can’t keep it up forever. Then when they meet me I think by the time the date has carried on for a couple of hours,  my less confident and  shyer  side comes out (I’m social, but not a huge extrovert). I think that is the stumbling block for me. If you’re not a flirty, bantery type personality naturally (I’m definitely working on it, but it’s not really in my nature to be that way with people I just met), is it misleading to be that way in writing. I don’t think as quickly on my feet in person with a stranger. Is that a source of confusion/disappointment for people, do you think?

    I can, and am, definitely working on being more flirty in person, but I’m very much a wait til his your boyfriend to have sex person, so the combo of the bantery messages, being more flirty in person is likely to give people the wrong impression…sorry if I’m being tangential, this has been an ongoing issue for me, so love some advice.

    Thanks all!

  10. 50


    In a joking sense, the movie 40 year old virgin is pretty spot on: Seth Rogan to Steve Correll…. “If you want to talk to a woman, just ask her questions.”

    I have found that every single woman wants to be pursued, and wants a man to “take charge.” (Not in an authoritarian sense by any means) but she wants you to pursue her with confidence; meaning initiating the conversation, asking questions, choosing the “first date” (When the time comes) . Don’t scare her away with a cheesy pick-up line you may find clever, and don’t ask her to meet too soon or hang-out at your place for the first face-to-face meeting. (This online thing is sketchy enough to begin with.) Read her profile and ask her a real question about something she described about herself. That will tell her you actually read her profile, and are interested. Continue a normal conversation until SHE is ready to meet. If you try to move too fast, she will be scared away in a hurry.

    Never stop asking questions, but questions with some substance!

  11. 51

    Well a conversation is a 50/50 thing. What I am suppose to be the entertainer here ? You can’t have an entertaining conversation if the other person isn’t contributing.

  12. 52
    Mrs. Online Dater

    Lol…I personally think this is all bullsh!t…Lol! If two people meet online and they are INTERESTED in getting to know each other, they will converse and exchange questions. Period. It’s that simple…stop making it seem as if there’s rocket science to it..lol. Now some people just aren’t good at holding a conversation online. But you don’t need to pull out all of these extra tricks to get someone to respond to the same type of questions that you would ask them if you both met in person. Lol? All this “look in the mirror, be more intriguing…etc”..really? You don’t want to ask questions that are too off the wall or left field but ice breaker questions is   all that should be needed IF both people have a MUTUAL interest in each other and are both giving each other that impression. Some people just won’t return questions because they liked to be CHASED!

  13. 53

    This sounds exhausting! I don’t remember having to work this hard when I was in my twenties to get a date. I also don’t understand why women expect the men to do all the initial work.

  14. 54
    Riley Reed

    So basically women are boring and need men to make them interesting. Funny how women reveal themselves and don’t even realize it.

  15. 55
    Adam F

    I could not disagree more with the conclusion posited by this author, that she is not asking questions because you have not given her a compelling reason to. No. You are interested without her giving you a compelling reason, because that is normal and that is how initially attracted works.

    If a woman is initially attracted to you when you meet online she will ask you questions as well. if she is not asking you questions but she is responding, she is interested in you being her pet counselor. An emotional tampon if you will. Keep asking her questions without her asking you back, and she will continue responding to you but she will never be yours.

    The answer that you should have been given at the beginning of this article is that yes she is just not that into you. Lift at the gym, continue developing your financial and career value, and you will get more responses in time. That’s the down dirty truth.

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