Holla at Your Boy: Finding the Heart to Approach Men

by Janelle Harris

You never saw it coming. You’re standing in line at Starbucks, waiting for your fancy frappe mocha caramel latte whatchamacallit thingamajig to be whipped according to the specifications you had to repeat three times and wondering how in the hell you managed to rack up a $15 tab for a drink and a little pastry when you spot him.

Up until now “breathtaking” had been a word dusted off as a corny reaction to stuff like the vastness of the Grand Canyon or the New York City skyline all lit up at night. But this man standing three customers behind you in line was just that: breath-ta-king. It’s all you can do to get a grip on the specialty drink the girl behind the counter finally managed to get right. You flash him a 1,000 watt smile. He grins back. You give him a smoldering, Jet-Beauty-of-the-Week stare down. He keeps grinning. At this point, it only makes sense for someone to approach the other and spark this love connection since, in but a few nanoseconds, you’ve managed to picture your wedding day and what your children—twin boys and a girl—will look like. The question is: are you going to be the one to make the first move?

For a brief period in our lives, usually from pre-K to fifth grade, girls dominate the dating game. We knock dudes upside the head on the rug during reading time and inform them that they’re our boyfriends. We lay out the rules and expectations of our contrived new romances and they fall in line faster than groupies with backstage passes. Two days later, we’re chasing a new beau across the playground, plowing over the has-been ex in the process. It starts and stops just like that. Then somehow, as we grew up, we lost the power to call the shots. Slowly but surely, we get sucked into this social conditioning that we have to wait for guys to speak to us first, ask for our numbers first, call us first, initiate the date first. Considering most guys think they’re on a communication roll if they’re putting three cohesive sentences together at one time, that’s a pretty big gamble to take.

Contrary to what you might have heard or told yourself, though, being the first to approach a fine-looking fellow doesn’t take an incredible amount of sexiness, beauty, even confidence. It’s more about being personable and approachable than it is about having all the right one-liners and a presence that oozes sexuality. As much as the average brother would like to think he’d be armed and ready with a set of impressive innuendos and witticisms if Melyssa Ford should happen to saunter up to him, he’d probably fare much better in real-life conversation with the random chick at Starbucks visually sopping him up like a biscuit on gravy.

Truth be told, guys actually welcome the break from having to do all the pursuing since that shift way back in middle school when old-school mamas and grandmothers drilled into their little girls that it was appropriate to wait for a boy to call them, not be the one to do the calling. So anything from the cold/hot/nice/crappy weather to the music blaring from their car at the gas pump can be the conversation piece you need to break the ice and get that holla going. If the chat falls flat and nothing comes of it, there’s absolutely no loss, no rejection, no knock to the self-esteem. You were nothing more than a chatty gal making a little small talk at the A&P who kept it moving after business was done. But if there’s a little something to work with, you can weave that into a date, and maybe another and another. Go on ahead and work that.

  • http://gravatar.com/lovegiraffes onegirl

    I said, ‘Is someone sitting here?’ My current boyfriend said with his deep voice, ‘No. You are.’ He got me! We talked and laughed the rest of the afternoon/evening and the rest is history. I don’t think that I really approached him first because I was honestly just looking for a seat to watch the football game. It didn’t hurt that the guy sitting next to the seat was as cute as could be (dimples, nice teeth and all), and later I found out he was single. *score* You never know where you’ll be when the one comes along.

  • MimiLuvs

    Slightly off topic: A friend of mine had once told me that I flirt, when I don’t even know that I am doing it. Then she gave me examples, including reciting examples where I had fixed dinner plates for men (who are guests) and smiling and greeting passersby (I was being polite). Since when did committing acts of good manners were considered flirting tactics? So, apparently, I’ve been unintentionally “approaching” men for a long time.

  • LadyP

    I like how you met your current boyfriend – really sweet and cute!

  • MK

    You know I was told the same thing? And worse because I like to smile a lot LOL

  • DownSouth Transplant

    Never took those classes in the playground, I am always lost on flirtations, that in turn it gave me hutzpah, I always ask directly “do you want to go out with me ?” mostly it has been not really I am not looking, or Yes if i was not married or Just what about tomorrow night kind of thing, my feelings & ego are never hurt because 1) I know i cannot read flirtations, 2) My ego is not attached to a total stranger, saves me the time & energy. A few of those have turned to great friendships, which I can count as enriching my life. My bestie hates it (being too direct) but always want me to ask on her behalf, SMH

    On the other hand my significant other walked up to me while I had eyes for someone else & asked me out, Years later, I still think it is the best thing I ever did to turn my eyes around to see him.

  • http://gravatar.com/lovegiraffes onegirl

    The really funny thing is that I was going to a sportsbar where there is a younger crowd, and I hadn’t been to in years (because I’m not younger anymore). Because of this, I was trying to look extra cute. I had on make-up, which I rarely wear, a cute sweater and jeans that say “HELLO!” I wasn’t able to find a parking spot when I got downtown, and I almost left. Suddenly, someone pulled out of their spot and it was right around the corner from the sports bar. After talking to this guy a while, I was like ‘how old are you anyway?’ and he was a year younger than me. I have to say, it was definitely fate, serendipity, God tapping me on the shoulder saying it’s time.’ Something!

  • LadyP

    a cute sweater and jeans that say “HELLO!” ~ This! #LoveIt :)

  • Kristi

    Never really had the confidence to make the first move….not even as a child. I always just sat there and secretly crushed on the boy I liked in elementary school (did the same thing in middle and high school to btw…). Never told him. We just walked around the playground as “buddies” until he moved in the 5th grade. Caught up with him on facebook and tried to get the conversation going between us by messaging him (still fine as all hell!). My friends encouraged me to make the first move and “talk” to him but I never did. Today (three years later) he’s a happy newlywed….. : (

    Story of my life. I can never get up the courage to talk to men. They give me “the eye” and smile, I just never know what to say…..still kinda shy at heart I guess

  • EST. 1986

    I don’t have a care in the world about dating, so I have no reason to approach men unless I need to get information and that is who is around. And, If it weren’t for my introverted personality and non-caring about dating, I probably would have to approach men because the men (and boys who mistake me for being in their age group) who approach me aren’t even men who I would be friends with.

    Just to note: McDonalds sells ‘frappes’, which is a cold beverage. Also, a drink can’t be a latte and a ‘frappe’ at the same time.

  • Starla

    I am not approaching any man with romantic intentions. I like the thrill of the chase, and I am sure the men I attract like the thrill of the hunt.

  • D.T.


  • Stanley

    If a man finds a good thing when he finds a woman, what does a woman finds when she finds a man?

  • Stanley

    I wish you good luck.

  • Mr.vicious

    A womans skill is to stand there and get a mans attention, so he will come over with his skill.
    A woman’s skill is her beauty, women don’t know how to get a dude, women don’t know how to talk their way in to nothing.
    Women never have to talk their way into happiness or try to figure things out and get rejected on a regular basis.

  • seriously?

    Isn’t it the worst? I hate being shy !! the first guy I like in over 5 years because I’m soocially and awkwardly clueless :(

  • Crys Mack

    When he finds a WIFE! Not just a woman. Let’s be clear…

  • http://gravatar.com/mimiandy1683 MimiLuvs

    Hopefully, she finds a man…
    … and she doesn’t end up in her own version of The Crying Game.

  • http://gravatar.com/mimiandy1683 MimiLuvs

    *snaps fingers and then slaps a bongo*

  • justanotheropinion

    I hear you Kristi! Some of us just don’t ‘have it’. I wish to God I did, but I can’t bring myself to make the first move.

  • Stanley

    Should have said Wife and Husband, but you get the idea.

  • Dalilah

    Men are only into looks. if you’re considered “hot,” a woman can approach whoever she wants. I guess you can get away with if depending on how you look..

  • YouHave2Wonder

    Omg, I hear the same thing. Since I’m always smiling guys always think I’m showing interest and women think I’m throwing myself at men. When I go to clubs with my girlfriend, many times guys approach me oppose to her. I know it’s only because I’m smiling and I don’t seemed bothered to have friendly conversation. So apparently I’ve been flirting but I don’t have the heart to approach a guy.

  • Candi V

    I don’t think that a woman should ever have to approach a man because…
    A.) Men enjoy the chase; even a shy man will get up the nerve to talk to you, if he deems you worthy.
    B.) If a man doesn’t get to pursue you then he knows he has you and we all know what happens when a man knows he has you and gets comfortable.
    C.) Which is kind of B, but I couldn’t let it go… when a man knows he doesn’t have to do the work in a relationship, he doesn’t try as hard. You may run into an issue when he meets someone he really is willing to chase. And maybe he was willing to chase you, but you never gave him the chance to do so.

    If you did give him the chance and he did not do it, well there you go. He decided he wanted to get to know you better over time (if he keeps running into you) or he silently passed on talking to you. As a quote I once heard goes, “If men keep staring, but not approaching you, then you need to step up your beauty game.”

    Either way it’s far better to wait for the man who genuinely couldn’t resist talking to you than to possibly push yourself on a man who isn’t sure he’s into you.

  • http://gravatar.com/jamesfrmphilly jamesfrmphilly

    now that is totally untrue…trust me

  • http://gravatar.com/jamesfrmphilly jamesfrmphilly

    i never approached women too much if at all. most of the women that i have become involved with either stepped up to me directly or got themselves introduced to me.

  • http://gravatar.com/jamesfrmphilly jamesfrmphilly

    the world is full of nice looking women. dime a dozen. men that i know are always looking for smarts and character. always.

  • Clay

    The only time a woman has approached me is when she was handing me a Watchtower Magazine or trying to get me to join Amway, otherwise I’m invisible to them.

  • http://gravatar.com/ravsmith78 Ravi


    Watchtower or Amway. That’s funny.

  • http://gravatar.com/ravsmith78 Ravi
  • http://gravatar.com/ravsmith78 Ravi

    Well, I suppose you’ll never find out. You won’t be dealing with any that might be attracted to you that don’t approach.

  • http://gravatar.com/eynapanirb B.Payne

    This may come off a bit snobbish and by all means I’m not….

    But I’ve learned that guys, young and old, appreciate the challenge when you let them approach you. I tried the other way and I started to feel like a man on the chase for HIM because he played me like I was “in need”…that’s happened a couple of times with different guys.

    I’ve concluded that my dad/brothers were right ;)

  • http://gravatar.com/ravsmith78 Ravi

    Right for many, perhaps, but not everyone. I hate the challenge and approaching in general.

  • PJ

    You are right but unfortunately desperate women just don’t seem to get it. You might “get him” for the moment but I doubt you’ll keep him interested for long if you desperately threw yourself at him when you first met! Most guys like the thrill of the chase, you’ve pretty much taken that away if you went after him. I’ll be fair and say 9 times out of 10 this is true. :)

  • http://gravatar.com/eynapanirb B.Payne

    To be honest, Ravi, I like organic meets…scenarios like we’re all at an intimate house party and group conversations that turn into one-on-one conversations or we’re all having a great time and we mutually exchange information as friends which turn into something nice :)

  • http://gravatar.com/eynapanirb B.Payne

    Based on my experiences, you’re right. The guys that I attract seem take pride in being the chaser…I guess too because I’ve been told that I smile alot probably makes it easier to approach.

    I will say that my now sis-in-law of 23 years brought it to my brothers attention that she wanted to date him…however, my brother/sis-in-law had been friends 5 years prior to her approach.

  • http://gravatar.com/ravsmith78 Ravi

    I’m with you on that one. That’s the preferable scenario. I’m big on mutual interest and reciprocity. If it’s too much of a challenge I’ll likely lose interest.

  • Kema

    I agree! I’m aggressive but I had to learn that falling back worked better. I think men respond better when they choose. *ducks*

  • Do better

    Totally agree, there’s something desperate to me about approaching a perfect stranger in public for romantic purposes. Maybe because I find it distasteful when done to me, but it could be a Sean Smith doppelgänger (my perfect man specimen from the Miami dolphins) and I still wouldn’t even look his way. Maybe I have a huge ego, but I just can’t give a man I don’t know the satisfaction of knowing he could have me. If he turned out to be a womanizing dog I’d curse myself for adding fuel to the fire.

  • EST. 1986

    So, when women approach men, it makes them ‘desperate’?

  • http://gravatar.com/ravsmith78 Ravi

    I hate the chase. I would venture to guess most shy or non-assertive men feel the same way.

  • Lulu

    You know what happens when I see a guy I find attractive? I put on a world class poker face and keep my eyes straight ahead while my heart does backflips and I pretty much whistle and catcall in my damn head. I’ll say its a defense mechanism from being rejected by guys in the past and I want to avoid reoccurrences at all costs.

    I want to change but I’m naturally very shy and reserved and coupled with this fear…*sigh* God help me.

  • Pseudonym

    You’re not supposed to CHASE the man. It’s more like just putting him on notice that you exist and you’re friendly. Then let him take it from there.

  • Pseudonym

    Or, on average, men from the U.S. are less forward and direct than their ancestors. Having lots of guy friends, I see quite a bit of admiring/pining from afar- especially from my nerdy guy friends.

  • Pseudonym

    Not true. Ask around to beautiful women. My more average looking friends get approached a lot more than my beautiful ones- especially by average guys. And this is by men who don’t know them so they’re going completely off the physical.

    It’s a common and incorrect assumption that beautiful women get approached more. Now in a place filled with high rollers or attractive successful men, that may be different. But since- on average- we find ourselfs among the average, beautiful women are less likely to be approached.

  • AM

    @ shawty the sweetie,

    He is NOT! C’mon, this is ma boo!!

  • AM

    so, does that mean you like being chased?! Enquiring minds need to know……


    It takes a lot of cojones to approach a total stranger and start a conversation. Women don’t have cojones, literally. However, if you’re a woman, and you really want talk to a stranger and show him that you’re interested, please be subtle, playful, witty, etc. Say something along the lines of “nice shirt”, then follow up with something such as :it looks good on you, or it’s sexy, upbeat, etc. That has worked on me on various occasions.

    That being said, even if you approached the man first you still have to play hard to get, well kinda. No need to go overboard but you get the picture… Unless you’re just looking for a fling.

  • http://myfemalepersuasion.wordpress.com myfemalepersuasion

    I agree. The one time I approached a man and gave him my number (a train conductor that i saw in passing everyday), it didn’t work out. This, after flirting in passing for months. I vowed to let them approach me going forward. I do agree with the article that friendliness goes a long way, and that if I smile and say something friendly (not even flirtatious), if he’s available and interested, he will take the bait. Ironically, I meet guys in grocery stores when i’m dressed down or on my way from the gym.

  • http://myfemalepersuasion.wordpress.com myfemalepersuasion

    I believe there’s some truth to this because men approach me more when i’m dressed down in gym clothes or grocery shopping. If I’m wearing makeup or dressed for work (corporate job), i hear “you’re beautiful” or “good morning” rarely get asked out. I think it’s due to lack of confidence on a man’s part to approach beautiful women. It’s easier for the “average” man to approach an “average” woman. What they fail to realize is the man with confidence wins.

  • http://myfemalepersuasion.wordpress.com myfemalepersuasion

    I agree with what you’re saying about complacency on the part of the man who is being Chased by the woman, but sometimes men stare because you ARE beautiful and they lack the confidence to approach. Doesn’t mean you need to step up your beauty game.

  • http://myfemalepersuasion.wordpress.com myfemalepersuasion

    And that’s fine. There’s a type of woman out there who you don’t have to chase. Someone for everyone. As a woman with a dominant personality, a man would have to actively pursue me for me take him seriously. Unless his intention is to just be a friend. Then that’s cool.

  • http://gravatar.com/ravsmith78 Ravi

    What people are supposed to do is opinion. I can just as easily say men aren’t supposed to CHASE women. Regardless, why does anyone have to chase? I prefer the scenario that B. Payne describes above.

  • http://gravatar.com/ravsmith78 Ravi

    Exactly. All men and women aren’t the same and there’s somebody out there for every type. You don’t take guys seriously that don’t actively pursue you, and I don’t take women seriously that would make me pursue them. And that still works out because there are enough people out there that will accommodate our preferences.

  • http://gravatar.com/ravsmith78 Ravi

    The reason might be that many guys are attracted to things that are counter-intuitive for many women. I personally prefer a beautiful woman in workout clothes with no makeup on. I’ve never met a beautiful woman that I didn’t think looked better without makeup. It might be that the men that approach are similarly attracted to natural, unmade-up beauty.

  • CanV

    So you want the woman to do all the work for you? SMH

  • WB2

    OMG. My big bros name is Ravi. Aside from Coltrane’s son, I haven’t come across too many ‘Ravis’ who AREN’T from India! lol. wait. let me not assume you aren’t. :-)

    Anyhoo. Yeah. I feel for guys- the expectation that they should approach each time and yet…as much as I’ve try to be progressive, I’m a bit old fashioned. I do think there is something to feeling an energy with someone you meet organically (house party, through friend, etc) and riding that out, being open, ya know? But I’ve tried that whole ‘hold your gaze’ thing and end up either looking crazy doing that Tyra ‘Smyze; or just bursting out laughing.

    Also, in more casual settings, I’m a funny person and while men say they want a funny woman, i find men to be a little intimidated by that. In my 20′s I tried to dial that back. Like be at an intimate gathering and try NOT to be…well..funny. But that didnt work.

    One time, i did feel the strangest connection with someone on a train. Usually i pay it no mind but it was clear there was an attraction but this felt like something else…but I got shy…i thought about the odds…and how many nutbags live in ny and when we both got off at the same stop, i kept urging myself to say something but didnt. boo to me.

  • WB2


  • EST. 1986

    I agree with you there, Ravi. I detest how one pursing another person is considered to be a ‘chase’.

  • EST. 1986

    Go to Starbucks and ask for a frappuccino latte or McDonalds and ask for a frappe latte and see what happens.

  • EST. 1986

    Right. That comment about a woman needing to ‘step up her beauty game’ rubbed me the wrong way.

  • http://gravatar.com/ravsmith78 Ravi

    I rarely drink anything but water and I never drink coffee. I truthfully don’t know much about any of this stuff. Just saw that link on the web.

  • J J

    Old women are desperate. lol hehe

  • http://gravatar.com/ravsmith78 Ravi


    I’m nigra. I’m from Detroit, but I do like Indian food.

    That train scene has played out with me numerous times over the years. 9 times out of 10 I have chickened out and don’t say anything. Boo to me too.

  • http://twitter.com/ShareefJackson Shareef Jackson (@ShareefJackson)

    Different strokes for different folks. I’ve never had a woman approach me straight up but I have had some drop signals that just seemed like someone being nice. I can see it as refreshing to have a woman be open and honest about getting to know someone.

  • Mr. Man

    Chasing seems (to me) is what’s reserved for players. Personally I’ve met wonderful women organically like SMH said. Thats the only way because it doesn’t matter who initiates it. Theirs no harsh or blunt rejections everyone is so afraid of, if you’re not feeling this person you just smile, tell them it was nice meeting them and both are able to move on with your feelings still in tact.

  • CanV

    When I say “step up your beauty game,” I don’t necessarily mean because the woman is unattractive. I have met women who go out in their sweats and don’t put in the effort to look attractive then wonder why they haven’t been on a date in a while and don’t have any prospects.

    I have seen women who dress like hippies but want men who are extra sharp and well put together. I am just saying that women need to look the part for what they want to attract. I firmly believe that you don’t ask for a man who is in shape, financially prosperous, and spiritually together if you are out of shape, financially in shambles, and a mess morally. I realize that this sounds like common sense, but many women miss the point and then wonder why they attract losers.

  • http://myfemalepersuasion.wordpress.com myfemalepersuasion

    Oh ok. This explanation is a bit different than the original comment. I agree that you should be/ project what you want to attract in terms of inner qualities, spirituality, etc. Physical attraction varies, because different people like different thing. Re: beauty game, i get approached by more men when i’m dressed down. I get stalkers in the gym too. Sometimes I’m surprised, but a man can tell when you’re a “put together,” beautiful woman who is just dressed down. SN: I wow them on the first date.

  • Stanley

    Have this ever worked for you or anyone you know?

  • Kristi

    Sounds a lot like me! If guys are looking for a woman to make the first move, then I guess I am out of luck b/c I am way too shy. Over and over again I am in this situation where I am clearly given the green light to come over and say something. But I am scared to death! Lord help us all….lol

  • WB2

    @ Ravi

    ‘Doc-tah- woop woop- Doc-tah DETROIT!’

    Sorry…couldn’t help me self! lol

    I too (as Halle so wonderfully stated in her role as Queenie) is nigras. From Harlem. I too have an Indian…well hindi name…so I’m obsessed with Indian culture…from the food (Chana Saag please??) to the Bollywood movies. :-) I plan to go to India for my b-day in 2013.

    Wanna hear something cray? I had such a strong reaction to that guy on the train that I put an ad on ‘missed connections’ I know. I know. We New Yawkas are nutzo…but you gotta give me one for hopeless romantic antics. OBVIOUSLY I’ve watched toooo many Rob Reiner/Woodie Allen movies.

  • http://gravatar.com/ravsmith78 Ravi

    LOL. you are dating yourself with a Dr. Detroit reference. Or maybe I am for recognizing it.

    I just had some chana masala a few days ago. My obsession ends with Indian food though. Not particular about Bollywood movies.

    I’ve never heard of missed connections before. I might have to check that out for the next time I chicken out in person.


    This is precisely why I personally don’t like approaching women. Everytime I’ve tried, nothing good has come out of it for me. I’m always respectful whenever I try, but I get responses ranging from the cold shoulder to indifference.

    Some brothers seem to be really good at meeting women off the cuff, but not me.

    For a pong time during my youth, this really affected my self esteem, buybi eventually learned to let it go, & do what works for me.

    Like alot of the brothers have said here, I prefer to be mutually introduced, or to meet someone in a gathering among friends. Or, of course, for the woman to approach me.


    It’s always weird hearing women say that they tried to approach a man once, & after it didn’t work out, they vow never to do it again.

    If men adopted that same attitude, the human population of the planet would drop to zero.

    For men, meeting people is a chore & luck. For women meeting people is a choice & a luxury.


    On the flip side, foreign men (especially African & Caribbean) are seen as being too aggressive.

    Can’t win for losing.

  • http://www.myfemalepersuasion.wordpress.com myfemalepersuasion

    @samairai36. It’s not a luxury for us its just the norm. It’s expected for the man to pursue. If he does’nt make the first move I’ll assume he’s just flirting or not interested. I’ve never been hooked up through mutual friends and I do admit that I don’t look twice at most men who approach me so I understand what you’re saying.



    People who are born into families, households, & communities with lots of money see their lives as “normal”. However, those of us without an abundance of wealth view their lifestyle as a luxury.

    But I have to say that your counter intuitive approach is what turns men off from what you think is “normal”, making it feel abnormal, at least for us men.

    This wouldn’t be such an issue for men like myself, if there were more women like the other women mentioned by others here. However the world seems to be filled with more women like yourself, than those other women, whom gentlemen such as myself feel more connected to, & find it easier to interact with.

    It’s a myth, that *all* men prefer the chase, & that *all* women prefer to be chased. And there is nothing wrong with their manhood or womanhood as a result. We are all different, & not meant to blindly follow pre-established social edicts.

    Just my 2 cents.

  • http://www.myfemalepersuasion.wordpress.com myfemalepersuasion

    I see your point. There’s no one size fit all scenario. If you have a preference as far as women, that’s understandable. Approach them, or if you have it your way, hopefully they will approach you. I don’t expect to be everyone’s type. Interesting comment re: counter-intuitiveness. I would agree with you if I saw men I was attracted to on a regular basis and shied away because I was waiting for them to approach. I don’t have an approach. Thanks for giving me some food for thought though.

Latest Stories

Because You Need Guns in Bars, Schools, and Churches Georgia Gov. Signs Bill Allowing Them There


Beyonce Captures TIME Cover & 100 Most Influential List


NeNe Leakes Defends Porsha Williams: ‘Not Porsha’s Fault’


Cheers! 30 Not-As-Obvious Occasions That Call For Champagne

More in Relationships
Passing the Relationship Bar: Getting it Right the First Time

Plan B: Settling or Settling Down?