Home Featured How Do You Approach Women? A Satirical Analysis of Today’s Conundrum

How Do You Approach Women? A Satirical Analysis of Today’s Conundrum



I was walking to the train a few days ago to begin my morning commute when I walked past a young lady who I would say was dressed nicely. I didn’t say anything to her, I didn’t give her any forward looks, but for some reason she did everything in her power to never make eye contact with me. I know why and this isn’t about that. I sat down on the train that day and I decided that if there was one question I could never answer for one of my male readers it would be “how do you approach women?” The only answer I have for them is, “I don’t know bro, wait for them to approach you.” As if that’s ever going to happen…

Here’s what I know does not work:

You can’t approach them on the street.

Whatever you do, never approach women you do not know on the street. If you are unaware of the reason behind it, just google the popular search term “street harassment.” Everything you need to know is there. The male population will have no further comment on whether we think that’s a good idea or not. We will respectfully remain quiet and not talk to women we do not know on the street.

If you were looking to approach a woman you didn’t know perhaps you could meet her at a bar, lounge or club. (I only list all three because Lord knows how people classify the places they hang out at these days.) The problem with this is there’s a great chance, as in 90% or better, that she only came there to hang out with her friends. If she actually did come to meet men, she most likely came with a friend. Women don’t like going to bars alone because it makes them look like hoes. They haven’t realized how awkward it is for a man to approach two women to talk to one. They also haven’t realized that two men approaching two women is also weird because nothing serious can come of that. I’m not going to see a girl that’s the woman of my dreams and say, “Hey bro, let’s go talk to those two chicks. I want you to be a part of the story of when I met my wife.”

You could approach women with whom you’re already friends. This is provided she or you hasn’t decided that dating inside your social circle is bad business. We all know the pitfalls of dating in our circle and if you don’t listen to Babyface’s legendary song, “And Our Feelings.” until it suddenly makes sense to you.

You could let your friends set you up in a situation to approach women. For example, you could go on blind dates with people your friends think are right for you. But then you’d be faced with that same old feeling everyone has on a blind date. That, “No… just no… why did you think I’d like this person?” feeling.

tumblr_inline_mfh1vytuTr1qh7z34You could approach women at work. This way you know them but you’re not friends. The only downside is when it doesn’t work out; you can’t quit your job because you quit your relationship. I guess this is why they say, “Don’t shit where you eat.”

I came up with a short list of places that we don’t need to waste a lot of time analyzing if you can approach women there:

  • You could approach them in the grocery store – Yep, you’re picking out meats and she’s buying tampons.
  • You could approach them at a wedding – And then you could deal with the drink in your face because she thinks you’re just trying to get laid.
  • You could approach them in an ice cream parlor – Sure thing, DMX. (Depending on your age, you may not get this joke. It’s ok. Honestly.)
  • You could approach them at a community service function or church – But that makes you either a bad Christian or a disingenuous philanthropist.
  • You could approach them at the bowling alley or movie theater – It’s dark, it’s loud, it smells and you rolling up on somebody in those circumstances raises your creeper alert to the extinction level.


All this boils down to a sad conundrum in dating: it’s almost impossible to approach women. They have to approach you. If they don’t know you, they’re scared of you because of what you might do. If they do know you, you’re in their social circle and off limits*. I was talking to a guy when we tried to find places where you can approach women. Later that day a woman complained about being single and that she couldn’t find any men to date and I looked at her, “Child please.”

Actually I did find one place where it’s okay to approach women… a blog.

Let me know if you guys disagree or agree. Also, don’t forget you could possibly meet your boo today in the comment section. Don’t believe me? It’s already happened several times over.

Dr. J

*I put an asterisk here because I want to remind you that I do not believe the “Friend Zone” exists. It’s a mythical place that people go when they give up. Most men just need to Philippians 4:13 the situation and make it happen.


  1. “Pimping ain’t dead it just moved to the web” – Pimp C

    Its funny how the tide shifted, people went from afraid to met strangers on the internet to more afraid of strangers on the street. I think it’s a control thing, you can start convo, end it, ignore it, block, and even get a view of how they act when you’re “not around”.

    Oh and I did meet an ex girlfriend at an ice cream parlor, because nothing looks as harmless as a ninja eating ice cream

  2. nah i don’t approach. i see a SBF in the street, in the club, in the grocery show i’m walking to the other side expeditiously and with post hates #NotAHarrasser

    honestly i met 1 on twitter…cool person. wouldn’t recommend it now, seeing what it has become. best avenue now might be if/when i leave the country.

    Philippians 4:13? lol, that’s a new one.

  3. Sometimes from reading people’s comments and posts, I could see why approaching women could be tough. In actuality, it is an “approach me with respect and learn to bow out gracefully” type of situation for most of us. Me personality, if a guy moves me, i’m going to say something to let him know, and the ball is in his court at that point. I’m trying to make the situation a bit more user friendly.

  4. “It’s almost impossible to approach women” – And this is why I think dating sites do so well. it provides the middle ground to make both sides approachable. It takes a little of the heat off of that initial ” hey “

    1. I don’t know where you guys live, but where I’m from you approach women you find attractive enough to approach by simply walking up to them and saying hello. You can make a comment about the weather, or even better pay her a compliment. Whatever it is that you find attractive about her, tell her that. Real simple and easy.

      I have total strangers (men & women) make small talk with me quite often. Possibly it’s because I look “approachable” (whatever that means), or so I’ve been told. I have no idea what makes people think they can just walk up to me and start talking as if I know who they are. But I am a pretty light hearted “go with the flow” type of person. So when people do just start talking to me out of the blue I respond in turn. I was raised that it’s rude to not respond to anyone that talks to you. I don’t particularly like being stared at so I will just speak to someone if they stare, (or ask them if they want a picture to last longer).

      At any rate, I don’t see what the big deal is. Unless there are new laws that I’m not aware of, simply saying hello to someone and paying them a compliment is not a crime.

      1. Truthfully its about 85% insecurity and the rest is ya basic pool of unapproachable looking women. Also here in NY we’re on the move so much its tough to stop a chick in the streets and get ya small talk on. It’s really all about timing.

        1. you ever tried to tell one that they had the stanky face? it’s crazy how they react. I actually dated a girl for a few months that was like, “yeah people say I look mean, I don’t get it, that’s how I look.” I was like man change your face then.

        2. Even more likely these days that face could also be (at a club, wedding or, corporate function):
          “Is he one of the “ones” who don’t like Black women? Better not waste a smile on him.” or
          “What number am I today? Do you just holler at EVERY woman you see? ‘Aey Yo You!'”
          As far as the “street” think goes I might think:
          “Why would an attractive male have to talk to a woman on the street? He can’t meet a girl at work, a bar, school, etc..?”
          That’s what I’m usually thinking, but depending on the approach and quality, I still might give a hello, but when they figure that I don’t want to take it further than that, I get called out my name. I’m in my twenties, and I have witnessed this sense the darn fourth grade! The only men who’ve tried to “holler” at me on the street have been thuggish types. In a very overtly lustful, salivating, over eager way! As if their lives depended on my willingness to give out my number? I don’t get it….

          And people need to be realistic and know their “status.” Not saying you can’t reach for higher. But know your range. For instance: If you’re 45 trying to talk to a 23 year old! (Yall know who you are!!!) That’s just desperate and unrealistic.

        3. While you’re thinking “what number am i today?” or Do you just holler at EVERY woman you see? ‘Aey Yo You!'” dude might be thinking “damn i’ve never done this before should I try now? she’s really pretty “..and we end up walking right past each other…bad and sad at the same damn time..lol

        4. Not necessarily, it’s all about what your attracted to, so you’re saying Peter and Cynthia from Atlanta housewives relationship is unrealistic? Me personally I’m 29 confident and very optimistic and if I see a woman that’s attractive to me no matter how old or how young I’m going to approach, my philosophy is if you don’t want anybody saying anything to you stay in the house lbvs. I’m seeing all these men talking about how they’d rather use social media as a conduit for interactions with women which irks me because to me, physical interaction should almost always be first method and everything else is an alternative. Don’t worry about rejection it happens to the best of us.

        5. IMO there ARE limits. Anything less than half your age is gross. I think grown men or women trying to holler at teenagers is gross and shows a lack of self discipline. And 50 year olds at young twenty somethings. Anytime it has happened to me I was very repulsed by it. No one wants WRINKLY-(insert shriveled body part/s here). Some men think every young woman is just gonna fall for their sleezy-greasy and they need to refocus those energies on other things. I can’t step out my door without perverts rolling up on me in cars or drooling at the damn gas station. Have some damn self-control! Don’t treat women like prostitutes and men might get a number every now and again. When I purposely dress down it’s even worse!

          “Don’t worry about rejection?” No. Body language IS a factor. I don’t approach men. They approach me. But I was just saying my initial smile would be wasted if they are the kind who “believe the hype” if you will.

        6. Mr. SD U talk on the subway/train/bus/plane. At the gym, at the park when your running or rollerblading, in the market, laundrymat. It’s spring so now is the time.
          Not necessarily walking down the street when people got places to go and things to do. Yes it is about timing. Timing is Everything.

        7. I agree, and truthfully when I apply the timing rule I get great results. I guess those moments are rare though, and probably because its suppose to be that way.

        8. Long time lurker.


          Just wondering, have you done what you’re asking men to do, i.e. approach men with the same techniques, locations, and confidence that you’re asking us to approach?

        9. Absolutely Mr. C. I’m a “people person” 🙂
          It comes natural and it’s easy for me to spark up a conversation with pretty much anyone. I get it honest from my family. They’re all the same way. They can spark up a convo with the people at the check out lines, gas stations, anywhere.

        10. Actually, it’s Mr. € the symbol for euros.

          Have you ever noticed that sparking up honest conversation with someone is different if you have romantic or sexual interest in them.

        11. Hi Mr. €,

          I think what makes it harder is the expectation and anticipated rejection. The idea that you have to become whatever it is this woman or man wants you to be in order to generate interest, a phone number,etc. Not to be funny, but when I see someone very attractive, successful, or intimidating, I just imagine them doing something human: blowing their nose, tripping over their shoe, etc. It takes the pressure off the approach. I do it at networking events all the time—-YES, even approaching people when you’re supposed to can be nerve racking:)

          No matter the setting or who you’re approaching, you have to believe “I”m a good person whether this person wants to talk, give me his/her number or not.” I’d say confidence is half the battle. I”ve had people not want to talk to me before, but I shrug it off. I think I’ve become a graduate of rejection therapy. (I used to knock on doors for political campaigns-now THAT’S rejection!) BTW, networking events are a great place to meet new people. I”ve found elevators are good too! I actually prefer small talk when I”m in an elevator and its just me and one other person.

        12. If you don’t approach you may miss out due to self inflicted limitations.
          As my mom used to say “closed mouths don’t get fed.” ijs

        13. ‘If you don’t approach you may miss out due to self inflicted limitations’

          I agree with this advice, which is why I tell women this all the time.

          And this “closed mouths don’t get fed.”

          I agree with this as well, but we might be talking about two different things. Lol

      2. “I have no idea what makes people think they can just walk up to me and start talking as if I know who they are”
        So you were born with friends? I mean, don’t all of our “friends” start out as people we don’t know? I didn’t get that point. Or do you only associate w/your family members?
        How do you get to know someone without opening up your mouth and finding out if you have common interest? People aren’t mind readers…

      3. “You can make a comment about the weather, or even better pay her a compliment. Whatever it is that you find attractive about her, tell her that. ”

        I disagree. Telling a perfect stranger what you find attractive about her is too much. You don’t know what that person’s boundaries are.

    2. The only difference between saying “hey” online and “hey” in person is that your face to face in person, and online it’s easier to lie about appearance. Only difference between rejection and acceptance is physical attraction. And it works the same for Both sexes.

  5. Loved this…especially the scriptural footnote. *waves my church fan* …cause it ain’t real, for real, lol.
    I’m with Payne. Now, I technically live in the south (Bmore ain’t really the real south tho). But, as we’ve discussed here previously, street harrassment has levels…and the levels tend to be higher and more dangerous in some cities (like NY) vs. others. Where I’m from, a respectful approach just about anywhere is fine. For example (true story):
    (sitting with my 10-yr old waiting for my take-out)
    Suitor: Hey there! Hello, young man…
    Me: Hello!
    The kid: Hi…
    Suitor: Nice day out, isn’t it? Nice change from the cold…
    …Me & the kid say something to agree
    Suitor: Big plans for the weekend? Supposed to be just as nice…
    Me: Eh…not really.
    Suitor: Well how about chatting with a new friend?
    Me: Sorry, I can’t. I’m in a relationship. But thanks for offering…
    Suitor: Alright, no problem at all. You two enjoy the rest of your weekend.
    …Me & the kid offer goodbyes
    The kid: Well, that was weird…
    See? Smooth as eggs, LOL. No issues at all.

    1. Kudos to the brothas cool intro and exit, even though “the kid” thought it was weird. He will learn in time.

      1. My boys grill me about strangers talking to me…”Do we know him?” “Why is he talking to you then?” “What does he want? I’ll explain “hollering” eventually, lol…

        1. Tip:
          Don’t explain “hollering” so much, that makes it seem as if you were being hunted and they have to protect you from being hunted down. Just explain that the nice man (if he was) was just seeing if we were compatible, and that you explained in so many words that you weren’t.

  6. I don’t approach for a few reasons listed, like why can’t we say hi if we see you walking down the street?? We may never see you again

    1. You can say ‘Hi’, but you don’t get to act a fool when you aren’t responded to.

      Likewise, you should be paying attention to body language and lack of eye contact.

  7. Harassment and approaching are TWO different things. It seems that you guys have lumped them together. Men, nowadays are fraidy cats…too in tuned with their feminine side. SMH. I’m in the South so this is odd for me. Yes we have harassment, but we also have men who approach women… For whatever reason timing is mostly wrong as I get approached by guys when I’m trying to get someplace and I’m pressed for time. If I have the time then he’s almost always unavailable to start with. Similarly men and women, to whom I meet, assume I am unavailable/attached. I’m not ugly, nor do I walk around mean muggin. I’m told how pleasant I am…refreshingly calm I am…easy to talk to and get along with, and then I’m asked often by men why do I smile so much…..give me a break! Demned if you do or demned if you don’t. I’ve asked men for their take and the men I know feel men are intimidated by me. My response to that is “Punks!”

    I will approach a man as in engaging in small talk, but I will not ask him out. If I did that, then I would be the boss, Lol! Right now I’m good but at some point I will want a relationship.

    1. I agree 100%. I think that in the major cities in the NE corridor it’s a more crowded population and that leads to more street harassment where women are thinking it’s more likely than not going to be harassment. In the South, where i’m from as well, it’s traditional to speak to every Black person you see because you don’t see them often. That makes it easier to approach women because of that social dynamic.

  8. Interesting, informative piece ::head nod::

    I think the subconscious is at work when it comes to a man’s seeming inability to move in the direction of a woman he’s interested in. The right scenario makes it easier, but ego, fear of rejection and lazy interest stifle the man’s natural inclination. Men who don’t stand a chance will approach any woman that piques his interest. He will approach the “unapproachable” woman even if she’s in a group. He’s bold; perhaps he has less to loose…less ego that is ;-).

    I do think men and women should create opportunities for introductions. Once, I intentionally left my girlfriend alone for a few minutes in a bar because I knew it would open a window. I came back and a guy was talking to her. I created the “safe space” for him, but in the end, most women want to know she moves a man…

    1. “Men who don’t stand a chance will approach any woman that piques his interest. He will approach the “unapproachable” woman even if she’s in a group.”

      Right. Men will complain about how it is tough to approach women, when their problem is that they frequently approach the wrong women, ignore body language and lack of eye contact, can’t take no for an answer etc.

      1. Ha ha. Yes, I guess there is the whole inability to read signs
        and heed warnings.

        I was thinking of the underdog that tries his luck despite the odds. There is something slightly enchanting about his pure will. It’s as if rejection can’t break him down, or he’s grown immune to it. The average (or above average) guy hasn’t quite developed that muscle. The underdog’s ego is not perched high in a tree, instead it’s chilling in a rocking chair – that helps him go for what he wants…even if he looses.

  9. This is interesting. I never thought guys thought about all of this. I’m approaching 23 in a couple of months and my “future husband story” always consists of me being at a matinee movie by myself and a guy who’s also by himself approaches me in the lobby or just happens to sit next to me in the movie and makes me laugh. Something corny like that. I do a lot by myself for the most part unless I feel like inviting a girl friend. Movies, mall, eating out. So it’s a little annoying how the rare times that I am approached it’s done completely wrong. It’s not so much where you approach but how you do it and at least SOME physical attraction. But then I also remember that no one likes rejection and guys fear that so .. What can ya do right?

    1. wait men are fear rejection??
      Last I saw were only the ones willing to put ourselves out here too be rejected. 10 out of 10 times.

  10. nothing wrong with grocery store approach–only if you’re checking out the same goods. Just don’t be so obvious in your approach. A wedding is do able as long a it’s before she starts drinking, maybe at the beginning of the reception especially if you’re seated at the same table. Bottom line you can approach a woman anywhere as long as you come correct with your approach and are being yourself. Just strike up small talk, if it leads to a conversation you got one foot through the door, and if you can snag the math then you’re in.


  11. The street (as with anywhere else) simply requires one to pay attention to visual cues (i.e. body language, brevity of responses) to indicate a woman’s interest/disinterest in communicating. Not sure why in these times people are finding it so difficult to interact face to face with a woman of interest.

    Perhaps its due to the rapid evolution of social media and the heavy reliance on it to the point people are literally living out their social fantasies from behind a screen, which ultimately hinders their ability to interact in the real world with real people. Just a theory.

    Mr SoBo

    Two Reasons You Should Avoid Break Up Sex


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