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

woman frowning in front of her laptop

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 (67 Comments).
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  1. 1

    Also, if her profile is lame and generic, expect her responses to your emails to be the same. Don’t be surprised when a chick whose entire profile consists solely of the phrase, “I love shopping, traveling and my dog,” doesn’t have a clever retort to your email.


  2. 2
    Karl R

    I’ve done the Opinion Opener before, with very successful results.

    The profile’s title was:
    Who said, “Be the change you want to see in the world.”
    When reading the profile, I noticed that the lady was a liberal.

    So the subject of my e-mail was: I know who said “…”
    And I started the e-mail with:
    It was the same person who said, “What difference does it make to the dead, the orphans and the homeless, whether the mad destruction is wrought under the name of totalitarianism or the holy name of liberty or democracy?”

    I then suggested that George W. Bush should have that quote duct taped to his forehead until he got the point.

    I think I got a response within the hour.

  3. 3

    I receive about 100 e-mails a week from men from online dating…soooo
    From the female perspective…

    1.) Humor works nearly everytime. If I don’t think we are a good fit by looking at your profile and pics alone sometimes good wit and humor may sway me. Notice I said sometimes and may. If i see pics and think “no way” or age range is way off, it really doesn’t matter how funny you are.

    2.) Both grammar and spelling count! (No I am not an English Professor, but don’t want to date anyone who I find less intelligent than myself. What would we talk about at breakfast?)

    3.) I have to look at your profile and be interested in getting to know more about YOU to ask YOU questions. I am what I consider to be a polite dater. I will at least glance at, but perhaps not peruse, a profile prior to responding. Be persistent if someone really strikes an interest, and give the girl a couple chances to read your profile. Take time creating and choosing the photos in your profile. I have, at least on one occasion, not responded to an email because the main photo had what appeared to be his ex with her face scratched out standing next to him. LOL Take time to provide photos of doing something that is of interest to you (ski pic, water sport pic, gardening pic, whatever you are into.) She needs to see that a date with you might be fun!

    4.) Last point here. The world of online dating is really not a level playing field. Several attractive men I have had the opportunity to meet from online have shared they do not receive e-mails and initial contacts in droves as we women do. Therefore, sometimes it is also a matter of timing. If you happen to email during a busy week for her, or where she is receiving 40 mails in her inbox per day, consider yourself fortunate just to receive a hi back. I will admit that online dating is not my full-time job and sometimes I just can’t keep up.

  4. 4

    People can go too far with the questions:

    This one guy wrote to me once- he seemed interesting, but his e-mails were full questions like- “if you were a slice of pizza, what kind of topping would you want on you?” At first I was amused, then just irritated- it’s not like any of these were serious questions- and this guy genuinely seemed to feel that they were!

  5. 5

    I do like how you turned it around on her. Too many people expect the Earth from others and do nothing to deserve or inspire it.

    Yes, men could try harder. Yes, women could too.

    Here’s the thoughtbomb: PEOPLE should try harder. They should be better and love each other more and stop making excuses for themselves and others and SOCIETY and carpe the freaking diem. But most of them won’t. And most of us are most of us.

    Yeah I don’t even know where I’m going with this anymore. But good post.

    *trigger finger, click*

  6. 6

    Hey Evan,

    I would advise this guy to read and re-read his profile to make sure it’s as interesting as he’s trying to be. Having said that, don’t try too hard! Water rises to it’s own level, as they say. Here’s an example from today from a man who’s trying to be funny, but…

    “Hi, you ask “What is your idea”????. Well my idea would be for someone to help me run away from home to start a new life. To beg me to move to Montana. Please please, help me run away. Adults can run away can’t they???? I know, you meant idea for a date, just put my true feeling spin on it. How am I doing so far???? I always wanted to live in Montana, was searching the profiles and liked your photo. I know this can’t work, just thought I would say hi since you view me back. Wish I was there.”

    Um…I’m not really up for saving this guy…11 years older than I, over a thousand miles away, not particularly attractive (to *me*) with an extremely mundane profile, five sentences long. The profile and pics are what we have to go on, and, of course, your charming opener! And really, most women, and men, don’t want to play q&a over the I’net with a stranger, they want to MEET someone. If you get a response, ask her out.



    1. 6.1

      Sorry but I read it before about asking a woman out fast, but that doesn’t seem to work. Most of them would rather chat some first. But it seems to be finding the balance between too soon and letting the messages drag on too long. I honestly would rather meet sooner than later too. I’m interested in things you can only judge in person and not over the Internet.

      1. 6.1.1

        I agree with you…Have to find the balance.   Actually everything you do in your life.   It also depends on how the person is and what their beliefs are.   Everybody is different.   Some people like or don’t mind long distance relationships.

  7. 7

    That was one of the best responses I’ve read Evan. People are boring the heck out of other people all the time and they don’t get results! Dahhhh!!!!! You have to intrigue them. What has worked the best for me is to do exactly what Evans advice is…find one thing interesting in the profile and comment on that…and have a great profile yourself! I totally agree that confidence and humor are the 2 most important things – by far. Sometimes when I run across a profile that I really like and they are from out of town, I’ll comment just to say they are witty, or pretty, or whatever. I did that recently and I’ve got a date lined up with her…she just happens to be coming to my city! And she’s HOT !!! And after all, it’s just a compliment! Give it if you feel it…if you don’t, move on.

  8. 8

    Some people are just uptight.

    I have been out with some who are just silent. I can ask them questions on a date and they respond to every questions with, “um… I don’t know?” To date some women is just dating a corpse.

    The on line situation, could be the same thing. This guy could be after these women for the wrong reason. Young, big boobs, in shape,… that does not always equal a good conversation. I find that some women, not all women, want to have everything done for them. They want to be swept off their feet, they want the guy to do all the work. Some women feel if they put up a profile, they have done all the work they need to do. From there it is 100% of the guy’s job to do what he needs to do to get her.

    The guy could be uptight when he writes to these women. Relax and let it come out. Try not to judge yourself too much. It is suppose to be fun, do not treat it like a job interview. Above all, I feel that the person you are with should be your friend if nothing else, someone that you can have a good time with.

    With a friend, you have confidence in them. You can share things with them. With a partner, it is that plus a little spark. A partner is someone that you can do a lot of the same things with, but still wake up with her in your arms. Granted, you are not going to play full contact football with no safety gear, like you would with your buddies, but you know what I am talking about.

    I say try to at least establish a friendship with these women. If you to hit it off, but the spark is just not there, she is a good reference. Chicks know other chicks. If you leave a good impression on her, she is going to tell her friends about you. Network, network, network…… It is all about meeting new people and building on social skills.

    I might even suggest reading “what color is your parachute”. It is a book about job hunting. The same basics can be applied to how you search for that someone special.

    After all, that is what dating is all about, building on current skills, gaining new skills, and finding what you really want out of life.

    1. 8.1

      Thank you! I thought I was shy, but some of these women make me look like a master conversationalist.   And the worse it when conversation is flowing like water online, and then we meet, and she has nothing to say.

      1. 8.1.1

        …the average woman has little to say, at the first meeting….

        1. hunter

          …part of their “defense” mechanism…

  9. 9

    Right on Paul!

  10. 10

    re: #8
    “I might even suggest reading what color is your parachute. It is a book about job hunting. The same basics can be applied to how you search for that someone special.”
    That’s an interesting analogy. What do they write about job hunting there?

  11. 11

    The book has been rewritten since the 70’s. Some of the things that it talks about is the internet is a tool not a magic wand. It is to be used like you would use any other tool.

    Know what you are best at.
    Know what you want.
    Talk to people who are interested in the same thing.
    Do research in some of the organizations where you might want to be.
    Identify the people you need to impress.
    Show this person that you are a solution to their problem.
    Do not be bothered by rejections.
    Do not cut corners, do not take short cuts.

    It is all about human interaction and how we are successful when in the company of others.

  12. 12

    “Do not cut corners, do not take short cuts” looks particularily inspiring 🙂

  13. 14

    I agree with EMK. Many times, we expect the world to serve us.

  14. 15

    May I suggest that some of this goes beyond just emails. I find through observation that the type of personality that is very self-focused seems to have become more and more dominant in today’s society. I’m not qualified to say why, but I suspect it is partly because our society encourages people to think only about themselves to survive and compete. You can’t completely blame people because it is getting more and more difficult to compete.

    Of course, other factors include that the person could be born with a self-centered personality. I find that many people do not think of “asking another person a question”, but they just want to talk about themselves. Career counseling tells you to not forget to blow your own horn to get noticed. Since few people attend schools on good manners and social graces, career counseling is the most information they are ever going to get.

    A long way back when social graces were encouraged, a part of this was making sure that you did not monopolize a conversation, and that you asked the other person questions and showed interest in what they had to say. This is dying away. Some people might think that their good looks or money and things will suffice.

    Having spent time with “wind-bags” who excessively talk about their own accomplishments, but take anything you can manage to interject into the conversation and twist it around into how it has to do with them! For example, you might say you were skiing at a particular place, and this person might respond with “That’s nothing. I was at this much better/more expensive/etc. place.” And then continue to ramble on.

    I look at that and other incidents, and I always try to remember not to be that person.

  15. 16

    Li-Ann, is that the response you get? How awful!….

  16. 17

    So what is the procedure for meeting people online? What exactly has to be written?

  17. 18

    casual encounters, how is it depressing?

  18. 19

    I sort of agree with what Li-Ann is saying, though I have nothing but anecdotal evidence and my own subjective experience to go on. Isn’t self-centeredness meant to be a real “Gen Y” thing?

    In which case, argh, it’s only going to get worse. Hold me.

  19. 20

    casual encounters, how is it depressing?
    They are no substitute for a real relationship.

    Casual encounters are better than nothing.

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