Online Dating: Mistakes Men Make In The First Conversation With Women And How To Fix Them

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This is a blog post for men sincerely wanting to date women, and who are having trouble in our land of online dating.

1. Opening with a “joke” – DON’T
ex: “Did it hurt?” —> some variation of “when you fell from heaven” “when you crawled up from hell” “when you [something explicitly and sexually gross]”
So, you want to catch her attention and you want to make sure she notices, so you go for a joke, or a question-joke combo. The thing is, you and every other guy on the planet is trying some line, so it’s no longer unique. In the best case scenario, yeah she responds positively. But in the worst case scenario, she rolls her eyes, finds you cheesy already, and moves on. Actually, there’s a scenario worse than this, which is: you use jokes at the start that are nothing like your actual character or sense of humour. Either she dislikes it right away, and your actual personality could have meshed, or, she likes your initial jokes/sense of humour but as time goes on she sees you’re not really funny in a way she appreciates.

2. Opening with a term of endearment – DON’T
ex: babe, honey, cutie, darling, dear, baby, princess, anything else you can imagine a father saying to a very small infant daughter
Terms of endearment come later in a relationship. If you are not comfortable being called muffin, cutie patootie, squishycuteface by a total and complete stranger, chances are, the *grown woman* you are talking to is also not going to take kindly to be prematurely called by any term of endearment. You are not her father. She is not 4 years of age. Stop calling her cutesy names when you don’t know what kind of she-devil she may be on the inside. It also just feels like we’re getting catcalled by our phone screens, which is just upsetting. No one wants to be catcalled outside in the street, much less in our own homes, when we are peacefully swiping. Call her by her name because…

3. …You Want To Stay Respectful – DO
What does respect really mean? A lot of guys get confused by this. they think it means some type of old school chivalry, pulling out chairs, paying for meals, taking a hat off and whatnot. That’s not what I’m talking about and it’s not what most women are talking about either when we say we screen men to see if they are respectful or not. In simplest terms, respect is the very basic idea that every single person is reflected in every single other person at the level of the human spirit.  Yes, our outer selves are shaped by our lives, by our experiences, by what we have endured, but respect is a fundamental understanding of equality between all people. It means you are no better than a beggar, no worse than a millionaire. And it definitely does not mean you are better than a woman whereby she needs to be dependent on you, nor does it mean you need to grovel to seek her approval.

Here’s what it does mean though: you need to be able to see yourself reflected in her essential human nature. You need to be able to say “my human nature is at its core, the same as a woman’s. And her human nature is reflected in me, and mine in her.” That’s respect. And women who know who they are look for this quality in men.

4. Any variation of “I’m looking for a girl who isn’t like other girls” – DON’T
ex: “Wow you’re not like other girls at all”; “You’re so different from other girls”

You might think it is a great compliment to tell women that they are not like other women, but be aware that what you are saying is “I think women in general suck”. In a world that generally tells women they are lesser than men, many women will logically and rightfully read your statement as incredibly sexist, and that you do not respect the vast majority of women  in a general sense. This goes back to point 3: you want to ensure you’re showing her not only do you respect her,  but that you are a respectful person in general. Comparing her to *all womankind* is not a useful way to show you respect women in general. Instead, express your liking in other ways: tell her what you find attractive about her based on the conversation so far, and do NOT…

5. …Focus on her looks – DON’T

There are a few reasons for this. First, every single guy does it. You actually stand out if you DON’T do it. Second, it’s obvious you like her face – you swiped right, didn’t you? Actually, I know guys have a tendency to just swipe right a lot. I think this changes with age and personal growth as people become more discerning, and they eventually don’t swipe right as frequently. But the point remains: from her perspective, she’s like “yeah ofc you think I’m hot, but so what?” The reason is: women don’t usually swipe right unless they think your face is cute. It’s a given for them. If they’re talking to you, it’s obv they find you physically attractive, so saying it out loud almost sounds cheesy or cheap. If you’re going to say something about her looks, save it for a 3rd date, and keep it classy. Not “wow those lips could –  ” nope. Canceled. nuh uh. Try something simple like “That is a beautiful dress.” So instead of focusing on her looks, connect with her by

6. Focusing on her skills, aptitudes, accomplishments, goals – DO
Anything she’s written in her profile is fair game. Anything you found while creeping her Linkedin or facebook is not. This is a first conversation,  remember. Check out what she has written and see what resonates inside you. Did she write something about academics or her job that you also find meaningful or are interested by? Any places she’s traveled to that you have questions about? Also consider that you’re not interested in anything she does or who she is. This is an immediate red flag because it means even if you really like her face and maybe even her personality, you actually have a compatibility issue in terms of what your lives may look like.

7. Calling your ex clingy, berserk, crazy, bitchy, or any other negative thing – DON’T
This is a first conversation. Your ex has no business existing in a first conversation with a new person. But she was really crazy! You insist. My response: So? So what? The new girl you’re talking to doesn’t give a shit about your ex. She will however, instantly file away the fact that you speak negatively of exes, and that that may be her same fate should you both decide to part ways. Don’t get me wrong, people of all genders can be really awful. I’ve been awful. I’ve also been wronged. But none of that has place in a first conversation with anyone, because it’s stuff you save for sharing later once you have built up intimacy and trust and a genuine bond in a relationship.  “But WAIT,” you cry! “Wait,…”

8. “…I’m just being honest!” – DON’T
ex: “My ex was a crazy bitch – what come on, I’m just being honest.” ; ” Yeah that lipstick is like totally unnatural, I’m just being honest”; “I’m just being honest! you don’t want a LIAR do you?”

Ok. So. This is an increasingly prevalent thing I see happening, and the “don’t” I recommend here is not about actual authenticity. Of course no one wants a liar, and of course no one wants a dishonest response. The problem here isn’t about honesty: it’s about too much information. When you add “I’m just being honest!” in that way, it reeks of defensiveness, insecurity, and the need to share an opinion that in no way was asked for. It also demonstrates that you have 0 tact or appreciation for someone else’s life, experiences, or relation to issues that concern them. It is very telling if you are able to be unkind and honest but not kind and honest. You are not, in fact, telling it like it is as you think you are doing. You are telling her who you are, and who you are is someone who doesn’t know how to respect her as a human being. Instead, just be authentic. Do you feel weird that she asked about your ex? Say that. Say: “Hey, I feel a little weird actually talking about her, can we not?” Do you feel like you don’t like her lipstick shade in a picture? Good! Keep that to yourself because it’s her face you gigantic dink, and she doesn’t owe you anything about changing her face in a first conversation. This is a problem residing very merrily in the land of: “I have an opinion on a thing! The thing is likely something that rests under YOUR purview but I’m going to share it anyway!” What DO you do if you hate her lipstick in that one picture? You consider for yourself if you’re ok with it or not. Give yourself permission to like things about certain women and not about other women. But don’t try to change the personal preferences of women you meet. Chances are, if you’re not into them, they won’t be into you either so long as you’re honest about that.

9. Ok, but I just really think if she [x action/thing I, as a man who wants to date her, prefer], then things would be [so great because then I can date her with complete peace of mind!] – DON’T

Do not advise a stranger about their life. Actually this one is so important I’m going to write it again: Do not advise a stranger about their life. This is a bizarre and strange thing to do. You cannot possibly know more about her needs in a half hour texting conversation than she does about her own whole entire life. All this shows is that you are interested in changing someone who you do not know very well, and are incredibly judgmental. Instead…

10. Get to know her – DO
Actually get to know her. Not her measurements, and not the 2D projection of her face on your phone screen. This is you putting your best foot froward and showing that you have the capacity to care about her as a human being. If you want her to get to know you, you need to show you have the capacity to get to know her. Be open to getting to know who she is without a lot of preconceived notions. Part of this process is recognizing what you like and don’t like about someone, what you accept and will not accept from someone, what you tolerate and what you will not tolerate from someone. And that stuff only comes out when you let it come out. And keep in mind: she’s doing the same for you. She is seeing, with a discerning eye, what you are bringing to the table too.

11. Bringing Your Man Ego to the party – DON’T
example 11a) Man Ego Alert: “I am now going to tell you about your job/career/interest/area of study/something I saw on your profile that you do that you definitely know more about than me but I want to share my opinion of what you do based on the 0 understanding I have of your work”
You sound like a damn fool, son. This is not partnership material. This is not even “quick lay” material. This is “wow, this man is a child, approximately aged five, tugging on his mama’s apron in the kitchen, giving her cute sounding advice about the very complex casserole she is making.” The ONLY appropriate response to this type of drivel from women is gonna be a real quick “that’s cute.” Because it’s cute. in the way a literal infant is cute. Instead, ask her questions about the work she does so she can share.

example 11b) Man Ego Alert: “But it was just a compliment! Why can’t you just appreciate a compliment?”  On a lot of blogs for women, we’re told men like to be appreciated. Here’s what I’m going to tell you: do something worth appreciating before you demand appreciation from a woman especially in a first conversation. She doesn’t owe you *anything* at this point. You two are total strangers to one another. Demanding things from her right now is not the same as a polite and respectful ask. A good example of this is linked to number five, commenting on her looks, in the first conversation. You: “Omg I love your lips and your eyes…” Her:”Can we not talk about my looks actually?” You: “Omg I’m just complimenting you”. *record freeze* *rewind*. Ok men, what defines a compliment? Let’s think it through. A compliment is defined by the person *receiving* it. It’s only a compliment if the girl actually likes what you’re saying right. Otherwise it’s you throwing a comment at her and her curving you. And she gets to do that! It’s her body man, maybe she doesn’t want, in a first conversation, comments on her face! So you have two options at this point: you can either insist you meant it nicely, as a compliment, etc and that she should just take it or you can back off instantly and realise that what you experienced was actually just her boundary for how she wants to be treated. Take it or leave it. You can say “Ok, I don’t think this will work” and go on your way meeting women who will always accept your comments on them, or, you can say “Ok, Sorry about that – clearly my attempt at complimenting you backfired.” And I get it. It hurts right? A little sting. Because she clipped your ego, man! But here’s the thing, you can actually sit in that little sting for a bit and realise that you wanting to do nice things for her is still nice and kind of…vulnerable. And vulnerability is always good.  You making her uncomfortable with your desire is not nice. You insisting on your desire to comment on her face is not nice. But you stepping back and offering her a moment of vulnerability after she says: “Uh could we not talk about my face” is actually nice. She gave you a solid no, you can give her a solid “I understand.”

example 11c) Man Ego Alert: Projection. Suspicion.
We as women do not want to compete with the ex that wronged you. You might say “but girls do this to us all the time! They compare us to exes!” Maybe, and here’s where shit is not fair: we are living in a society that routinely blindsides women, asks us to be perfect while giving a lot of you passes for everything. We are asked to cook and clean and work and show appreciation, and be model hot, and be emotionally vulnerable, and be managing everybody’s emotions – so when we compare, we do it from a very real sense of self protection – and we are aces at it because we live in a sexist world that disenfranchises us every step of the way. This is not something you, as a man, are likely going to understand without a lot of work, but you gotta trust me on this: women protecting ourselves through comparison is usually not the same as men projecting their ex on every woman they meet. Part of the reason for the difference is that women, who have been taught from birth to manage our emotions,  actually have less bias when we do this comparison process. We do it with a more discerning eye. Men who often do not know their feelings very well because they haven’t been taught to be discerning are quicker to project negative traits without a lot of thought. This doesn’t mean you cannot protect yourself – you can and should  protect yourself emotionally because you are also meeting a stranger. The trick is to do it without projecting when she says something you don’t quite understand, or when she says something that you find yourself  reading a particularly negative way. Just ask her what she means. Stay open to the answer, but also stay discerning. You are interested in what she has to say but that doesn’t mean you have to accept it.

example 11d) Man Ego Alert: Defensiveness and Insecurity
You know what this is. You feel upset on the inside by something you can’t even fully name. You get mad. You try to assert control of the conversation. You try to assert a boundary but end up belittling her.  The only cure to this is comfort with your own boundaries, your vulnerabilities and your sense of self.  Which brings us to…

12. Be confident – DO
What is confidence though? A lot of men confuse this with bravado, ego, “chivalry”, “being a man”, etc. This is how I’m going to sum up confidence: Show her that you are at peace with where your life is headed and are internally a solid rock. You don’t have to be hyperactively happy about where your life is headed, or have a one-track excitement about it; all people are multifaceted, many people are living with depression, anxiety other struggles and confidence isn’t to say that someone cannot be vulnerable. Being at peace with your life shows her that you know yourself, are there for yourself, know your needs. In a first conversation, to be confident means that when you say yes, you mean it, and when you say no, you mean that too. At this stage, she is looking to see if you live up to your word, and to see if you can manage your own emotions in a healthy way. You shouldn’t be saying yes to everything she asks because that means you are just saying yes because you are worried she will leave. No one, regardless of gender, likes to see simpering, groveling attitudes. You also shouldn’t be saying no to everything she asks (unless of course, you find you dislike her, don’t want to be around her, and are losing interest in dating her) because if you keep saying now a) she’s gonna leave you , but more importantly b) saying no all the time means you’re not actually interested in partnership: you’re interested in controlling the direction of the relationship, making decisions, and never letting her take the lead because you’re scared of where it will go if she takes the lead. And that fear is part of insecurity. Confidence is the balance here:  being confident about your own life also shows you are open  to growth, change in a mindful and authentic way where you inherently trust the process. You trust that saying yes to things you want bring into your life things you want, and you trust that saying no to things you don’t want keeps out things you do not want. Confidence should feel like you’re on a sailboat, comfortable manning the thing, unafraid of the wind or the sea or the environment because you have yourself.

13. Show Interest and Be Receptive to Interest – DO
So many men these days seem incapable of making a plan. Make a plan, Stan! Not because we are incapable of making one, but because we’re actually annoyed that men seem incapable of actually formulating an idea for things. Here is what you need to make a plan:
1. an event, eg: coffee (let’s just keep it simple)
2. a time, eg: 7pm
3. a date, eg: Next Thursday?

This doesn’t mean you need to lay it all out like that in a single, motormouth second. “Uh so how about coffee next thursday 7pm?” no. canceled. stop that.
But what you can do is ask courteously “Hey, would you be into meeting for a coffee, maybe next Thursday?” Her: “Sure… yeah, what time were you thinking?” You: “Would around 7pm work?” Her: “Yeah that works great!” or “Actually, could we move it to 8? I have dancing with polar bears.”
Alternatively: You: “Hey, would you be into meeting for a coffee, maybe next Thursday?” Her: “Sure… yeah, would 7pm work?” You: “Yeah, that works great! ” or “Actually could we move it to six? I have dancing with polar bears after, so.”

See? A plan. Contribute details to the plan in a mutually organized manner.

Anyway dudely people, I hope this helps you all! And in the process, helps us women too.

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