Rules of Engagement: How To Approach a Man
Back in April, I wrote a post called “Should Women Ask Men Out? (Fear of Rejection).” For those that missed it, the basic premise was that when it comes to courtship all the pressure generally falls on men, while women sit back and either accept or decline their advances. There were varying opinions on either side of the fence. A fair share of men agreed that they wouldn’t mind a woman stepping up to the plate and making the first move. However, an equal amount of women sighted such actions would go against pre-established gender roles (blah blah) or having tried it once and never ever wanting to face that kind of rejection again (boo hoo).
Well, in the midst of all the women crying foul at the idea of asking a man out, one brave female reached out to me the other day saying she was willing to give it a try. Problem was she didn’t know how.
“I often hear, ‘Oh you are so pretty and have such a great personality, how can you be single?’ or ‘You are so busy and intimidating, maybe you should approach a guy first,’” she wrote. “Being that I am clueless as to how a man should be approached, a blog on the issue may help myself and others. Then readers can give you feedback on the outcomes.”
Thanx, Devoted Daily Reader, that’s actually a pretty good idea. Making a suggestion is one thing, but providing some real advice is always better.
When it comes to dating I’m a pretty simple guy, but I can be a bit aloof when it comes to women. What she may view as a clear sign of interest will probably fly right over my head. Even when I get an inkling that a woman might be interested, I have this annoying habit of finding some rationale that leads me to conclude that I’m not her type or I’m merely imagining things. The few times where a woman has asked me out successfully it was never about coy attempts at flirting but clear cut signs of interest. Whether or not we went anywhere came down to mutual attraction and chemistry. Most importantly, though, it was all about honesty.
I’m just one man with an opinion, and if I’ve learned anything over the years is that I don’t always think or view things the way the next person would. Rather than just giving my two cents on how a woman should approach a man, I opened the question up to my male brain trust and got an interesting mix of answers—some I agree with and others not so much—from the fellas. All in all, men like to feel wanted too. Ladies, you may agree or you may protest when it comes to asking a guy out, but this is how real men in the real world think. Well, at least the ones I know.
Speak your piece…
MR. DIRECT
“Just be natural. Nothing, absolutely nothing beats that. But I can understand that being hard for a lot of them because they’re not ‘trained’ in the art of approaching men. A woman can simply say, ‘I like you, let’s talk more, let’s go out or something,’ or something like, ‘I think you should ask me out, because I’ll say yes if you do.’ If the dude is interested, you got him right there. Just keep it light, because I hear that [asking a guy out] can actually scare off some dudes. With talk like that I don’t see how on Earth someone can think you sound ‘desperate,’ so to speak. More women should know that dudes love to see a grown woman get all softie because they like them. Show it, dammit!
Must be absolute hell for women to put their necks on the line like men do, but hey, you gotta pay to play.”
“…Wait up, if the chick is not attractive or fat, then these rules go out the window. Mutual attraction is VERY important. If you’re not then you should just randomly start bringing by pizza or something. They gotta do whatever it takes to win, even if it means being a sugar mama, or giving the world’s greatest head. Whatever it takes. LOL.”
MR. QUICK WIT
“A woman approaching a man doesn’t come off desperate in my opinion. She comes off confident and aggressive. I personally love that. From experience, girls that approach me are almost always clever. There’s always something slick or original to their approach. But since being clever is not given to everybody, the others should just strike up a conversation and slowly ease into asking the guy out. We aren’t as picky as girls. There aren’t ‘no-nos’ as far as girls hollering. The only no-no is a girl I'm not attracted to. No matter how good the approach was, I gotta be attracted to you for it to work. I say don’t over-think it. If you want him, step to him.”
MR. BARTENDER
“It’s really simple. When women approach us it’s a big turn-on. Just flirting hard or buying us a drink at a bar is good enough. Buying a drink is a major, big time turn-on for me. It cuts down the BS.”
MR. BUSY BODY
“If a woman wants to ask me out
I'm right here. I like what I like, but I enjoy surprises too. So, if she has tickets to the game, great! But if she wants to go to a nice eatery or something, that’s nice too. I’ve never been asked out per say, but I have been, er, aggressively informed that this one woman wanted to go out—badly. Ha ha. I say just go ahead and ask, and be prepared to pay. Because for me personally, I hate when women call me wanting to go somewhere but not want to pay. It’s not that I don’t mind, but it’s you that asked. So when you do that (repeatedly) it comes off as if you only call when you want something to eat, not because you enjoy my company. But, yeah, go ahead and just ask. But try to get a feel for a man’s schedule and ask according to that. And know that either way, if we really want to be around you, we will make the time.”
MR. SIMPLE
“It doesn’t matter when or where a woman asks a man out. I’ve noticed that most women are either shy or afraid of rejection. So they often don't approach guys, but in my cases, women have approached me in bars, clubs, and told me that they're interested. In fact, I'm more impressed and turned on if a woman comes to me with confidence and is interested in getting to no me better. All she has to do is stir up a casual convo and let it lead from there. Nothing more, nothing less.”
MR. FRIENDLY
“You know I did have this ONE chick buy me a drink and walk off. The shit was very strange. I think the easiest way for a woman to approach a man would be to act friendly and introduce yourself. Different settings would require different methods, but a friendly smile means hello in most languages.”
MR. BASIC
“If a woman wants to show me that she’s interested in me and wants to ask me out, she should start by being witty with her conversation. Drop flirtatious hints and maintain eye contact. She should have a place in mind, just to show that she's about teaching a brotha something, but if she just wants to go for a drink and talk, that's cool too.”
MR. TECHNOLOGY
“Definitely the worst way to approach a man is to throw out the, ‘So, when are we gonna hang out’ phrase. Me and my boys hear that and to us that just positions you as the ‘straight-to-the-sack’ type. The best way for a girl to approach is through convo, maybe through AIM, email or text. Just some good, cool convo. Guys love to talk about themselves, and if a girl is interested in him she wants to know about him anyway, so just ask and sit back. Then, after a good convo or two, hit him with, ‘We should talk in person, over lunch, or go to the movies.’ Guys can want a fat booty, and if they do, they're gonna go after it themselves. But for most, who have on blinders for booty only, you and he will win with a good convo that's not too direct and has the potential to blossom into something. Catch him with charm, jokes, and intelligence, and those short messages will leave him wanting to talk more. That’s what gets me.”
MR. APPROACHABLE
“Overall, it can be as simple as her starting up a conversation. I’ve been befriended by women before and as long as she keeps amiable and confident, I'll be receptive. I won't front; I usually expect a woman to just flirt with me and wait for me to make the first move. But confidence is the main thing. If a woman shows genuine confidence and asks me out, I'm more likely to be receptive. There's no specific scenario I require, at all; just sincerity and amiability—and a nice smile.”
MR. SENSIBLE
“Men and women are different in important ways, but we'd all do well to consider the things that make us alike, and make us all human. Therefore, the Golden Rule applies here: Do Unto Others, etc. Most women don’t want canned or rehearsed or insincere pick-ups lines, right? Suggesting they should refrain from using them on men they’re interested in should be a no-brainer. Most women like a drink as a gesture of class and largesse, right? I’d bet most men do, too. Most women like a genuine, maybe funny, maybe observant introduction (‘Hey, that martini glass must have half a dozen olives in it! You should try the olive tapenade appetizer if you like olives so much, my treat.’) I suspect most worthwhile men would appreciate that as well.”
“Women should also not take rejection or a lack of enthusiasm personally. Men often build up a tolerance for rejection from women over time (mature ones, anyway), stemming from being shot down over the years in search of ‘The One,’ or at least ‘The One For Now.’ (Some men have even gotten to the point where they just hold down their square and shoot game at female after female after female, the way a telemarketer cold-calls every Smith and Jones in the phone book till they get their sales quota). Of course I’m not suggesting that extreme, since the mark of a slut—male or female—is arguably a low-to-no standard in who they will get busy with aka ‘Who will I do? Anybody will do.’ But in order to be at one's best in breaking the ice with a cute stranger, they can't let desperation or fear show. It has to be all grace, all charm, and all swagger. That only emerges when the Inner Hater's doubts (we all have one, we all hear him or her talking us out of Seizing the Day) are put on mute.”
“Finally, many a man has complained about the woman who, on the first meet or first date, talks incessantly about herself and shows little interest in the guy listening. Some men have even incorporated this into their ‘game’—keep her talking about herself! However, in this day and age such indifference to getting to know the guy you're pushing up on is foolish if not dangerous. Don’t fall into the habit of finding strong and silent, or adaptable and endearing to be so irresistible that you end up falling for whom you've assumed this guy is, and not who he REALLY is. Plus, the guy might peg you as self-absorbed and write you off for anything long-term.”
“So ladies, mind your manners, find something fun to observe and remark upon (shows you are paying attention, and who doesn’t like attention from someone they think is cute or cool?), show genuine interest, be considerate and enjoy the flirty give and take! At the end of the day, genuine chemistry is genuine chemistry, and if you feel it he probably feels it too. Picking him up at that point should be a piece of cake, if he hasn’t already moved to pick you up—or book your digits—by then. Best of luck, ladies!”
Tagged as: bar scene, battle of sexes, dating, dating rules, men vs. women, poll, rules of engagement, what men think


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