in: Dating & Relationships

Reinventing the Pickup Strategy: Approach Like a Gentleman

You can have a mindful pickup strategy. If you are true to yourself, it’s not a pickup strategy at all. It’s simply an honest way to meet someone new.

Let’s face it. Pickup lines have never worked.

Maybe that’s an exaggeration. I’m sure there are some happily married couples who met when the man uttered just the right comment at just the right moment; but realistically, he was lucky that his lady was impressed; and she’s definitely not still married to him because of the pickup line he used when they were in college.

The art of picking up a woman is belied by its own label. The term “pickup” suggests an action that is contrived and insincere, and for this reason can never be taken seriously.

Pickup lines are easily dismissed as the musings of immature men, the quips of high school locker rooms and fraternity houses, traded to make each other laugh and never to be actually used on women. (I’m not knocking athletes and frat boys. I was both, but I’m trying to paint a picture of the referenced maturity level here.)

The problem is that the shallow and cynical essence of the pickup line, which has been categorized as ridiculous, has evolved into the pickup strategy, which is admittedly more cerebral but just as disingenuous and has unbelievably gained favor in some circles. These strategies employ classless methods with such subtlety that they go unrecognized as the pathetic attempts of insecure men and are often confused with the confident approaches of good men.

If I read one more article about how you should be able to get a lady’s contact information in the first five minutes, I’m going to lose my mind. If you are walking around with a pen and paper in your pocket, because you intend on getting several phone numbers and email addresses in one night, you are not smooth. You are a predator, and you’re taking the wrong advice from someone who thinks more about taking advantage of a situation than about meeting someone who might be worthwhile.

I say stop listening to these guys who are still bitter over the fact that the pretty girl was mean to them in high school. Don’t be fooled by the so-called life coach who finally grew into his face and got some nice clothes and a stylish haircut only to steer other men to the path of evaluating women as numbers using social experimentation. These guys are not Sigmund Freud, and although they claim otherwise, they have no clue of the psychological process of women in a social situation.

In my humble opinion, making the right impression is a matter of being comfortable with who you are and approaching with good intentions and a genuine desire to learn about someone new. Confidence plays a part, but should never be feigned. Your confidence as a man should stem from your security in the fact that you’re a good person with a lot to offer anyone.

That being said, let’s reinvent the “pickup” (I hate this term) strategy. Here are some very easy, honest and effective steps to follow. Let’s assume the setting is a bar for the sake of structure.

Say hello.

Here’s a novel thought. Introduce yourself like a gentleman, like a real person. If you introduce yourself with an air of false confidence or arrogance, you’re going to come off more like a great white shark with only one thing on your mind. That beautiful woman is not a conquest. She’s not a goal. She’s a person (who might be the coolest person in the world if you actually get to know her).

Don’t use feeble attempts to start a conversation right away. You can be observant before you approach. If you lock eyes a few times, that’s a good sign that she’ll be receptive to your introduction. But even if you decide to take the risk without an unsaid invitation, there is nothing wrong or threatening about saying hello.

“Hi, my name’s Matt,” can get the ball rolling better than you might think, and a conversation can grow from that introduction in an organic and interesting way.

Have a real conversation.

So many pickup “gurus” will tell you to use your environment to start a conversation. Talking about the guy who started a fight, the girl who’s too drunk or the bartender who ignores everyone might give you a temporary point of common ground, but it has no substance. People have interests, passions and opinions. If you make small talk for fear of bringing up something boring, you will miss the unique intellectual, artistic and considerate aspects of a woman.

Be perceptive enough to notice what kind of drink she’s ordered, what she’s played on the jukebox or if she’s clearly there to see the band that’s playing. These are ready-made conversation pieces, and you might find that you have something in common. If a woman orders a whiskey and plays Led Zeppelin at the juke, I know I can have a good conversation with her, but that’s just me. You’ll have to judge each encounter on the basis of what you observe and what you both like.

Beyond that, be yourself. If the conversation is left to you to continue, ask questions that you care to know the answers to (nothing too personal right off the bat) and choose topics that interest you. If you find that she won’t engage you on the subjects you allude to, you probably don’t have much in common. At least you’ll figure that out.

Don’t force popular conversations down her throat, and don’t assume that the best subjects to bring up are those that are ignorantly considered typically feminine. She might not want to talk celebrity news, fashion or community gossip. If you bring up Kim Kardashian’s ass, and she wants to talk about how the ESA (European Space Agency) successfully landed a robot on a comet, she’s an intellectual and you’ve already lost.

Compliment with caution.

If you’ve succeeded in having a good conversation, you’ve learned a few things about her. At this point you should be getting a feeling for if she likes you, and equally importantly, if you truly like her beyond an initial physical attraction.

Hopefully you’ve piqued her interest in a few ways while you were talking, and maybe you’ve even made her laugh a few times.

At this point, you can lend her a compliment. Tell her she has a great sense of humor. Tell her she’s really smart. Tell her she has thoughtful perspectives, but whatever you tell her, mean it. Don’t say anything just to flatter her. Make the flattery the byproduct of being sincere.

If your instincts are telling you that you have a special connection with this person, and you are feeling particularly bold, tell her she has a beautiful smile or that she lights up a room when she laughs, but say it because you felt it first.

Chivalry is not dead.

If all has gone well, and you’ve been a self-confident, perceptive, considerate, respectful gentleman, you will know by this point of the evening whether or not you’ve made the right impression.

If you have, you might be keeping that beautiful smile on her face regularly. You might be looking into each other’s eyes consistently as the evening proceeds. She might be asking you more and more about yourself, because you’ve intrigued her.

You definitely have gotten to gauge (this is a nicer word than judge) each other to evaluate whether you appreciate each other’s qualities, moral standpoints, even likes and dislikes.

At this point, it’s appropriate to pay her a serious compliment and inquire as to whether or not she might like to see you again.

Be sweet. Ask this as a question. Don’t say, “Hey give me your number. I want to call you this week.”

Say, “You’re incredibly beautiful, and it was a pleasure talking to you all night. Would you mind if I called you sometime?”

Try being chivalrous. See if that works.

Be a man.

She might turn you down, but take it like a man. In fact, take it like a gentleman.

Nothing is full-proof. She might have just been looking for good conversation that evening. She might not be interested in dating at that point or she simply might not find you as attractive as you’d hoped, but this is no reason to throw a hissy fit and denounce the female gender.

Even if you haven’t succeeded in getting her phone number or securing a date, you won’t be ashamed of your effort, and she won’t think a shred less of you for trying.

You should be comfortable with the fact that you entertained a lovely lady for a few hours, and you should be hopeful that such an approach will work when you meet the right woman for you.

About the Author:

Matt Mattei

Matt Mattei is no longer afraid to call himself a writer. After eight years in the construction industry, helping a burgeoning company grow, he stepped away from an attractive paycheck to do what drives him on a daily basis. He has found a comfortable home as an editorial intern for MeetMindful, and he is grateful for the opportunity. In his spare time he writes his own creative non-fiction, which focuses on his personal experiences and reflections. He hopes to cultivate a career as an editor and cultivate his skills as a writer.


Join our Mindful Movement!


Sign up today, and we'll share bi-weekly Mindful Moments, full of helpful tips, tactics, and content to improve your life!


"Without a doubt, the most engaging written piece on mindfulness!"

- a Mindful Moment Subscriber


(We'll never sell or share your information, either.)

You have Successfully Subscribed!