Online Dating: 10 Things Men Should Definitely NOT Do

Don’t you love all these dating advice sites for guys that are written by guys?  I think they are funny.  Here’s a guy telling another guy what works with women.  What the first guy is really getting from the guy he gets advice from is what works for that guy with the gals he’s meeting or being successful with…doesn’t mean it will work for you…unless what you want is what he’s getting exactly. 

To put it differently, it would be like me going to ask advice about how guys think from a woman.  How the hell will she know???  She’s not one of them.  She might be close.  She might even be right on.  I might even listen to her and take her advice, but not before I check it out with my guy friends.  The ones I know I can trust.  The ones who feel comfortable with me enough to tell it like it is.  These are the guy friends I would never date or become romantically interested in for one of two reasons:  a.) because they are married to my very good girl friends or b.) they would tell me point blank, “Hey, it’s just really hard to get romantic with one of the guys”.

So for all the guys out there, who hope to try to make an impression with a woman online so that you can put yourself at the top of the email pile and maybe even make it into her favorites list, I’ve provided this list of my top ten most reliable behaviors that will get a guy blown off, ignored or deleted.  

I confessed in an earlier post that I was a bit of an online dating junkie.  At one point, I was on, I think, three different sites at one time.  I’ve explored nearly all of the really notable ones, free and paid, for long enough to form a strong opinion about which approaches from men really work and which don’t work at all.  I’m pretty successful in the online forum for reasons that have to do with sincerity, truth and a good picture that really looks like me. Plus, I think it helped that I grew up as a tomboy.  (The Barbie Doll shoes really annoyed me.) I kinda get the mentality of bonding over doing something  instead of  the just talking thing…something most women don’t get but which many men, bless their hearts, endure anyway. 

But I’m talking and not doing, so I’ll cut to the chase.

10 Things You Should NOT Do When Approaching A Woman Online

1.  Don’t be self-absorbed.  Clearly, this should be a no brainer, but I’ve received a ton of emails where the man talks only about himself.  If I don’t know the guy, there’s nothing there to help me connect with him.  What you are thinking is you want to give her information that will help her make an informed decision about you.  Sadly, you’re assuming too much in what it is that she is making her decisions upon. She’s thinking, man if I get into relationship with him am I going to have to put up with him talking about him all the time?  She’ll hit the delete key, send a “thanks but no thanks message” or, worse, she’ll block you.

2.  Don’t treat this online forum as a job interview.   Would you do that at a cocktail party?  Would you start interrogating someone you were attracted to about their past relationships, their preferences for sexual frequency and whether or not they’d be comfortable with you coming up from behind and grabbing them by the boobs in public? (Yes, all these things have happened to me and to other women I know.)

3.  Don’t fall in love too soon.  Dude, until you meet her and date her…a lot of times…or, at least until she tells you otherwise…she is still just a digital image paired with some words.  Don’t go being all smitten and stuff and talking about how gorgeous she is and how you think the two of you were meant to be.  She’s making decisions based upon how you treat her, talk to her and think about her.  If you think she’s an “object” instead of a person, she’ll disappear. Treat her like another human being, not like the beauty you are attracted to.  She’ll become that beauty in your face-to-face life if you can respect her and love her for her mind and her contribution to this world (beyond just the airbrushed or real beauty).

4. Don’t be afraid to be you.  Women are all about relationship.  We want to connect.  We want to connect with those we relate to. If you are trying to be something you are not, we will see through this eventually.  Hopefully, for everyone involved, this happens sooner rather than later, but there are plenty of divorce statistics out there that state otherwise.  If you are a funny, humorous light hearted sort express that.  If you are more serious and thoughtful let that be apparent.  The woman you are hoping to attract will be attracted to the real you.

5. Don’t try to impress her with how many dates you’ve been out on recently.  That might work if you’re trying to impress the guys, but for use female types this simply translates as “we’re just one of many options” you have.  No one wants to be an “option”.  All of us want to be the person you’d slay dragons for.  If you try this approach we will read it as you’ve already decided that “you’re just not that into us”.  We’d be fools or unhealthy to invest in that.

6.  Don’t expect her to do all the work in setting up the first meeting.  Take the bull by the horns.  Suggest something, anything.  It is never okay to make her a.) call you when she’s free or b.) tell you what it is that she wants to do if you’re the one approaching first.  In this area, you must take risks and forge ahead trusting that if she is not okay with it she’ll be decent and kind enough to counter your proposal with another option.  If she kicks you to the curb because you missed on the first idea for a meeting, is that such a bad thing?   After all, if she treats you like that after such a kind gesture, do you want to be in a  relationship where that treatment is the norm?  I mean, really c’mon.  You’re a great guy.  You deserve some respect.

7.  Don’t ask her how successful she’s been in the online dating forum.  This question shows up like this:  “So, having any success here?”  or “So, I bet you have all the guys wanting to meet you!”  First off, we have no idea how to respond to that with kindness.  If we are successful and we tell you that,  what will you think?  (Please note that women, especially ones with good photos and well written profiles…okay…skip the profile…ones with good photos and lots of them…are going to get more mail than they could possilby respond to in a 24-hour period if they worked straight through.) If we tell you honestly that we aren’t having much luck…well…what will you think then?

8.  Don’t give up too easily.  Guys, remember, that many of us are single moms with careers and we might be homeowners in our own right as well.  (Meaning, we bought the friggin’ house ourselves and didn’t get it gifted to us as the result of a divorce settlement, death, or judge’s signature at the expense of some poor man who may have had to claim bankruptcy in order to avoid contempt of court charges.) This requires our time and if we are real people we won’t be able to respond right away all the time.  Kids have concerts, we have lives, houses need to be maintained and we simply need to sleep sometimes.  Be patient.  Don’t assume that because we didn’t respond the first time we didn’t care.  Don’t also assume that if our response is brief that we are just not that into you.  We might have wanted to connect, but the kids were demanding our attention, the account we have to have that big proposal ready for  is meeting with us the next day or the car dropped its rear differential in the street three hours ago and we have no idea how we’re going to get that repair done.  Please cut us some slack. We are willing to make room for you in our busy lives, but not till we know you’re going to be willing to accept our busy lives. Be patient.  I cannot say this enough.

9.  Don’t come on too strong.  I know that sounds strange after what I just wrote, but listen, if you pounce, you’ll suffocate.  You’d run too.  Have fun with it.  Don’t make it the end all most important thing ever.  Relax.  Friendships, relationships, love, is a bit of a dance.  Don’t force, just be the fun you, the thoughtful you, the true you that you are but be very careful of overdoing it.  I might add that if you feel like you are being you and at the same time you feel like you are coming on too strong, maybe you should pull back.  A woman in love can never get enough of her man’s attention or affection and she is always deeply appreciative of it even if she can’t necessarily carve out the time to respond at that exact moment.  If you are feeling weird about things, listen to that.

10.  Dont’ go silent.  Say something.  Understand that women are verbal creatures.  On the playground as kids you guys settled differences by physically laying into each other.  We, girls, learned the “more socially acceptible” method of being catty, using our vocabulary and really learning that words, as well as sticks and stones and fists, can hurt and leave deeper scars.  We also learned that words can create worlds, characters, perceptions and evoke really positive emotion too.  We live and love base on the words you tell us (as long as they match your actions).  Please, don’t just email us and say, “Hey!”.  Don’t email us with tons of pictures of you and your life and no verbal explanation.  Don’t just grunt.  We need to connect with you and we do it with words.  This is never more important than in the online forum where the first meeting is completely textual and verbal.

And I might add, that if you really want to make an impression you should consider what your elementary schoolteachers told you and use good punctuation, capitalization and accurate spelling.  Even if she’s not all that smart, your emails will be easier for her to read and understand.  If she is all that smart, she won’t give you the time of day if you can’t communicate well in writing.  If you find that too tedious, take your chances.  If  you can’t present yourself well in writing, what  makes you think she’s going to think you can present yourself well in person? 

Okay, have fun with that one fans and skeptics alike! I’d really like to hear perspectives that maybe I, in my finite wisdom, have not considered.  Do enlighten me.

In the meantime, enjoy your online dating experience.  It can be frustrating, heartbreaking and disappointing, but it can also be a great way to get to know other people in your world when your world doesn’t allow you to cross their paths in real time.  It can also be a great source for putting yourself in the path of romance.  After all, 1 in 8  married couples in 2006 met online.  I’m sure that statistic has grown since then.

5 thoughts on “Online Dating: 10 Things Men Should Definitely NOT Do

  1. Yes, you have said it all well. However, your side comment about the grammar and spelling, in my book that would be number one. If a man can’t spell or use grammar, he doesn’t even get the message opened. If he wants any sort of chance he needs to be proficient in writing at the very least.


  2. arg!

    In this day and age, this kind of connection is becoming more common. A lot of people aren’t really sure how to handle it.

    thanks for providing some insight.


  3. This is an interesting post, because you get to the heart of what frustrates many people about “advice”. Telling people what NOT to do is useless. Telling us what we SHOULD do and providing examples of how it worked for you would be far more productive. I couldn’t imagine what people would think if my response to their request for financial advice was to give them “Investing Strategies You Should Avoid”. Any dolt can tell you to invest in companies that aren’t losing money and you shouldn’t put all your money into on stock.

    Uhhhhh…OK. Thanks for the help.

    Seriously, some of this stuff is elementary, where the rest of it is contradicting and raises more questions. For instance, your first item says “Don’t be self-absorbed”. Well, what SHOULD a guy write to a woman’s online post if not an introduction telling the person a little about him?

    Another item you discuss says “Don’t give up too easily”. Seriously? Look, if you want a stalker then I don’t think online is the way to go. It is probably best just to head straight to a half-way house for sex offenders. There, you will find a place full of guys who don’t know when to take “no” for an answer. If life is too busy for you to take a few minutes to find a date, then hide your profile until you find a better time. Don’t expect the guy to keep e-mailing you when you haven’t responded. If you end up going out with a guy that nagged you until you responded, don’t be surprised when you have to eventually get a restraining order against him. You rewarded bad behavior, now you have to deal with it.

    But, wait …

    You get more confusing because you follow up “Don’t give up too easily” with “Don’t come on too strong”. WTF? All of a sudden I feel like I am “that person” trying to get in the car, but when I go to grab the handle, the car lunges forward and out of reach.

    First of all, guys don’t run when girls pounce. That is a bad assumption on your part. Instead, we go out on a date … with the pouncer (yes, I know pouncer isn’t a word, but it was funny and I am keeping it).

    Then, you go even further …

    The fourth item says “Don’t be afraid to be you”, but then in the ninth item, you state “if you feel like you are being you and at the same time you feel like you are coming on too strong, maybe you should pull back.” Uhhhhh, so I’m not supposed to be me? But earlier you said …

    AHHHHHHHHHHHHHHHHHHHHHH…dammit, it is so confusing!!!!!!!!!!!!

    Let’s all take a moment of Zen…………

    Give people examples of what has worked for you in the past and why it worked. Telling people what NOT to do just makes the dog that chases his tail look smart.

    (For the record, I don’t understand the online dating community and have chosen to stay away from it, so any advice you give would be for other people. I’m clearly on the record of wanting to be turned down in person. It is the way life should be.)


    1. Ahhhh! Do you have to be so da**ed intellectual about it all? 🙂 Those items you mention are not necessarily contradictory. For example, if you are being you, and you sense that she feels it is too strong, or conversely, not strong enough, then it might be an indication that the two of aren’t a good fit.

      Putting it in terms of what not to do, was an attempt, however weak and pathetic, to write creatively. Had I wanted a completely well documented research based article on what works, I could have written that also, but who would have read that without yawning.

      However, all that being said, as always you make excellent points, so I’m going to take you up on your challenge. I will write a post complete with examples from actual emails of what I liked and what I wasn’t so impressed with. I’ll do it, because it’s a good idea, makes sense and I kinda like the “dare ya” challenge.

      About online dating, I’m sensing you live in an area where there are possibly many opportunities to bump into people face to face or you have enough activities in your life that bring you into contact with datable people in the age range and interest categories you seek. This is not the case with all people in all communities. I happen to live in an area that has an incredibly high number of divorced and still single people. My daily routines and activities, however, bring me into contact with none of them. In fact, the last “friend” that I met through a friend from work turned out to be still married, no divorce even filed (!!!!!!!!) and they’d been separated for over 2 years. And the friends putting me in touch with friends doesn’t work for me since most of my friends are married women with busy lives of their own. Making an initial contact with someone online, exchanging just enough email to determine the guy is of average or above intelligence and then meeting the person for coffee or something light, is a pretty efficient way to get to know people I would never stumble across in my day to day routines. I’ve met a lot of people this way and made some good friends along the way. Don’t misunderstand me, there are many drawbacks to the online approach. I do understand that. I prefer to be rejected in person, like you, but I don’t cross paths with enough people who would do the rejecting otherwise. So, I’ve tried the online thing as a way to increase my opportunties. Think of it as a way to join a singles club without ever having to leave home unless you want to…(oh, I can’t wait to hear your comment on that one!)

      Thanks for your comments. As always, you do bring great insights and perspectives to the table. Do you have a blog? I’d like to read it!


  4. A) I love it when someone scolds me for being too intellectual. It reminds me of my boss telling me that I wasn’t a good employee because “you don’t need to win every time; sometimes you have to let others win.” It confuses me and makes me hold my head high all at that same time.

    B) Focusing on the things guys “shouldn’t” do is an interesting concept. It’s like The Family Guy episode where Stewie acts like a dick to a girl he likes to go out with him. I almost went down this road with Santiago awhile back, but I sobered up and realized that isn’t the direction I wanted to go. Suffice to say, many women, usually the hot ones, seem to be drawn to the negative behaviors of men instead of the positive traits about men. That is the real reason I feel you should write about the examples that have worked. Focus on rewarding the positive behaviors of people and delete the negative behaviors. There are benefits to pointing out the things people do that are wrong, but women will often reward behavior that isn’t beneficial to them and ignore behavior they should reward. Men probably do the same thing, but I don’t date men so I don’t know.

    C) I live in the Portland area and I work in downtown Portland, so I guess that gives me the opportunity to bump into people. It also means that I have a lot of chaff I need to weed through. Either way, it is frustrating.

    D) My blog is located at You can read all about my craziness there. 🙂


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