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. 21

    hunter: It’s depressing because it points out (rightly) that there’s no substitute for hard work and doing things right. For those of us who prefer to lie on the couch, execute sloppily, and cut corners, the bald truth of the assertion is disheartening to acknowledge.

    casualencounters.com/blog´s last blog post…Casual Encounters Web TV Show, Episode 1

  2. 22
    love by birthdate | birthdate compatibility


    At last a guy who understands how to communicate! Are you taken 😉

    It never fails to amaze me how guys can talk so much yet say nothing! Ihope that every guy who sends me an email reads this first and takes notice!


    love by birthdate | birthdate compatibility´s last blog post…Relationship Compatibility By Names

  3. 23

    This is great advice. I love how you break it down! I’ve found that flirting with light teasing or some trivial question is a great way to get a response from a woman. Playfulness is key. Make sure the questions are related to something in their post, but don’t ask for boring factual information. Like, if they say they enjoy riding horses, and you ask “where do you ride?”, the woman might ignore the question and move onto the next guy. If you say something funny yet respectful, you’ll have much better luck. (So of course, I have no witty horse-riding nugget to drop in this comment. Next! Haha)

    dadshouse´s last blog post…Single Parent Movie Date

  4. 24


    I never heard back from her.

    casualencounters.com/blog´s last blog post…Casual Encounters Web TV Show, Episode 2

  5. 25
    Karl R

    casualencounters.com/blog said: (#21)
    “It’s depressing because it points out (rightly) that there’s no substitute for hard work and doing things right.”

    While your observation is true, I’ve found a number of ways to “do things right” without making it feel like “hard work”.

    One of the main ways I meet women is through dancing. I love dancing, so I’ll spend hours each week dancing and socializing with women (regardless of their dating potential). It isn’t work. It’s part of my R&R time (and part of my exercise). A lot of women have told me that it’s obvious that I enjoy dancing. A lot of men and women look so serious when they’re dancing; I’m smiling, laughing and chatting with my dance partners.

    I’m relaxed and having fun when I’m dancing, which makes it easier for my dance partners to relax and have fun. Basic psychology works in my favor. These women subconsciously associate relaxation and fun with dancing with me. And when the women aren’t dancing, they’re talking with each other … frequently about the men.

    On the one hand, I’m spending an evening meeting some new women, networking, building/reinforcing my reputation, practicing my dancing/social skills and talking to women to find out if they’re the kind of women that I’d like to date. On the other hand, it feels like I spent an evening having fun with a bunch of women, some of whom are already my friends.

    I wish the rest of my work could be this much fun.

    1. 25.1

      OMG, Karl, (and I know this is considered “bad form” to do a “me too” kind of response), but ME TOO!!   I love love love dancing and consider it a form of wonderful therapy from my corporate job.   My co-workers and boss know to get out of my way at 5:00 on Wednesdays because that’s “therapy night” for me.   They all know I’ll be in at 7:30 in the morning in a GREAT mood and full of vim and vigor.   How refreshing to read your comment about how dancing is wonderful for meeting new friends,enhancing/improving a skill and just having lots of fun in general in a very social setting.   Wednesday is the start, but I could (and often do) go Thursdays, Fridays and Saturdays too.   It’s fun, one can lose weight (I lost 11 pounds over the past 6 months), and it’s great cardio exercise.   Thank you for your post!

    2. 25.2

      I should have asked in my response comment…do you say that you love dancing in your profile (if you date online)?   I’ve only tried one site, several years ago, and I listed dancing as one of my passions, and I was immediately dismissed by several viewers who thought it was “sinful” and shallow.   Was very discouraging.

      1. 25.2.1
        Karl R


        When I dated online, I mentioned it as one of the activities that I pursue.


        If a online dater  dismisses you because he believes dancing is sinful (or shallow), do you really think he’d be a good match?


        This is an old post, and I’m no longer particularly active on this blog (unless I’m bored), so it’s a bit serendipitous that I caught your question.


        I’m married now.   My wife and I recently celebrated our 3rd anniversary.   I met my wife at a dance studio during a break between classes.   We were introduced by a mutual friend (another dance partner  that I briefly dated).   We still go dancing regularly.


        Dating in the dance community:

        First, it’s a lot easier to keep dancing if your partner shares dancing as a hobby.   At the very least, try to introduce him to the community so he considers them to be friends that he likes to socialize with.


        Second, the people who go dancing for the sake of dancing (like you) tend to date a lot more than the people who go dancing for the sake of finding dates.   Most dancers can easily tell the difference between the two types of people, and the former are better liked (in all respects) than the latter.


        Third, when dating in the dance community, you want to end your relationships on good terms.   You’re likely to see your exes again (and again, and again), so its important to at least be civil.   If you manage to do well at having good clean breakups, your exes may be the ones saying nice things about you to your prospective future dates.


        Fourth, if you’re dating inside the dance community, judge your prospective boyfriends on how good of a boyfriend they are, not on their dancing skill.   When we go out dancing, maybe 10% of my dances are with my wife.   But I’m married to her 100% of the time, so it’s more important to get along with her the rest of the time.   (My wife has become a very skilled dancer over the years, but I would still have married her if she remained substantially less skilled than me.)


        Fifth, you may occasionally run across a dancer that you hardly ever see, but you would like to get to know better.   As a woman, you’re generally not expected to be the one asking for a phone number (or date).   Similarly, the men generally aren’t asking for a phone number (or date) the first time they meet you.   It’s not that kind of community.


        I found a great way to circumvent that.   While chatting with the woman, I would let her know where I frequently dance … or where I was going to be dancing on some day in the near future.   If she was interested in me, she would make a point of going places where she knew I was going to be.


        There’s no reason that   the same trick couldn’t be used by a woman.   You’re not inviting him to join you.   You’re just telling him the places you plan to go dancing … which gives  him the opportunity to show up and see you again.


        Online dating as a dancer:

        To put it simply, dancing was always a more productive source of dates than online dating.   However, if I ever hit a stretch where I didn’t think there were any potential dates in the dance community, I still had a second potential source of dates that wasn’t running dry.


        Essentially, it helped me keep my head in the dating game, even if it had been weeks since I’d had an actual date.

  6. 26

    Thanks Evan for answering this question and the fantastic advice!! It’s great to have someone like you who is so passionate about dating! I’m happy I found this blog!

    To give everyone some background, I’m actually looking for a long term relationship, so the wording in my profile is on that side and it’s is also funny but I’m considering using his profile service because I know it could convey what I’m looking for in a better way.

    I can see what Evan is also talking about when it comes to giving her a compelling reason to write back. I admit my email to this particular woman was on the side of “I see you like…bla bla bla look at my profile bla bla bla.” I have joked around in my initial emails but it fell flat, so I resorted back to the boring stuff.

    But after getting that “see if it was read” option on Match and realized they didn’t read it, I realized I was getting discouraged for nothing! They didn’t have an account to write back!! That was enlightening to learn that because there I realized that it wasn’t my humor that was falling flat but it wasn’t even being read.

    This is interesting too. I wrote to one woman who did the answering but no asking and she told me she just broke up with someone and wasn’t into it and was cancelling her account. So it’s a learning experience!

  7. 27

    I also wanted to agree with this statement from thomas:

    “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 are just dating a corpse.”

    I have had this happen to me because the woman are (what I figured) to have been hurt before, thus they don’t want to extend themselves, so they won’t feel they were fully rejected.

    Not putting down any women who have been hurt. I’m not a master conversationalist either so I admit I can do better to talk about other topics etc. but I feel (at times) women blame the guy for what they themselves do. But that goes to another post where Evan said online dating isn’t fair and people are hypocritical. Something you have to deal with and understand I guess.

  8. 28

    Yeah, I guess I was making the statement with a more general context in mind. You are of course correct that one can socialize and meet women without suffering undue personal hardship. And also that doing so doesn’t have to feel like work.

    casualencounters.com/blog´s last blog post…Casual Encounters Web TV Show, Episode 3

  9. 29

    Karl, don’t you get winded while dancing, making it difficult to chat at the same time?…..I have heard, some men can multi-task, mostly, the left handed ones.

  10. 30

    For many of the dances, you’re not so winded that you can’t talk (unless you’re doing a fast jive for an hour). But there are so many guys in my dance classes who the women can’t talk to during the dance, because if they do, the guy loses his concentration and can’t do the skill that’s being taught. Some guys (mostly newbies) are so focused on the maneuvers that they have no room for conversation. But the more experienced (or confident) dancers…now those are the ones where it truly is enjoyable, both because of the dancing, and the conversation!

  11. 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.

  12. 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.

  13. 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!


  14. 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

  15. 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.

  16. 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.       

  17. 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.

  18. 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.

  19. 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.

    2. 39.2

      Whomp Whomp. @Joel , with that attitude I expect online dating is very frustrating for you.

      Also, I expect you are a lot more fun than that rant suggests you are. If your dating profile sounds like this…

      I here for ACTUAL women that are ACTUALLY interested in talking. I’m tired of the same old crap on X. If you can’t respond to my messages, get this YOU SHOULDN’T BE ON THIS SITE.   blah blah blah. Whine whine whine.

      ….then perhaps reconsider your approach.

      And yes, I do want to be entertained by your messages. Yep 🙂

  20. 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!

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