[Thanks to reader and Fierce Gentleman Chris Behrens for submitting this guest post! – Andrew]

We’ve all been there in the moment – looking at her as she’s looking at you, and not having the slightest idea what to say next. You smile, she smiles, and then – nothing. The moment passes, someone else captures her attention, and the moment is lost – the opportunity to connect is lost. Connection is what we want, whether it’s as simple as a meaningful conversation, or as grand as a lifetime together. This connection is why we endure the rapid heartbeat, the dry mouth, the stuttering and the awkward silences.

This desire to connect is what you must focus on – when you focus on the connection, what should happen next becomes easier. Imagine if, rather than being at a party or another social situation, you were HIRED by an eccentric millionaire to walk up to a woman and connect with her – connect with what she does for a living, what she’s passionate about, maybe just what kind of movies she likes. What would you do then?

Of course, the millionaire paid you to CONNECT with her, not merely interrogate her, so this involves offering something up of yourself. Once you find this point of contact, then you can share a little bit of yourself and deepen the connection. So, the first problem you’re solving when talking to a beautiful woman is:

FINDING A POINT OF COMMON CONNECTION. . . THAT SHE CARES ABOUT

This is the premise behind pick-up lines, and while they generally fail so spectacularly, unless they’re played for a laugh – the premise is that the point of connection is the woman’s vanity: I recognize that you’re attractive, and I’m going to assume that that’s something you’re really caught up in. It’s a big lose-lose – a pick-up line won’t work on the woman you want to connect with, and the woman that it WILL work on, you probably don’t want to connect with in the first place.

ASKING QUESTIONS

Only she knows what she’s passionate about, and you need to find it out. You find out by asking questions…but what questions?

Start with, Hi, I’m Joe (shake hands), and then:

• So what’s your story?
• I’m here tonight because (single sentence explanation that requires no follow-up). What brings you here?

That’s about as broad a net as can be cast. Ideally, you have a common social context from which to take a cue, such as being at the same school, or place of work, or church.

Pro-tip: Be careful not to ask “Do you come here often?” There’s nothing inherently wrong with that question, but that specific formulation is a very tired pick-up line. You can express the same sentiment with “How long have you been coming here” or something similar.

PROCEED FROM THE GENERAL TO THE SPECIFIC

It’s important to not box yourself in too early in a conversation. If you have that specific social context to work from you can use that, but be careful. For example, in a coffee shop:

You: Hi, I’m Joe (shakes hands). What are you drinking?

Beautiful woman: Uh, it’s a cappuccino.

You: …uh, those are great. (Silence)

Beautiful woman: (Smiles) Well, gotta go…

What might have gone better is this:

You: Hi, I’m Joe (shakes hands). I’m grabbing a coffee in between classes. Same with you?

Beautiful woman: Actually, I just got off work.

You: Ah…where do you work?

Beautiful woman: I actually just started a job at this law firm…

And there you go.

Here’s another example of the wrong way to do it, and the right way to fix it:

In the lobby outside a movie (afterwards)

You: Hi, I’m Joe (shakes hands). I really love the films of Wes Anderson. What did you think of the Royal Tenebaums?

Beautiful woman: I just came here with a friend…is that the director of the movie?

You: Yeah, the writer and the director. He’s got a really idiosyncratic, hand-crafted style…

Beautiful woman: (no idea what you’re talking about) Sure. Well, nice talking to you…

And better:

You: Hi, I’m Joe (shakes hands). Did you enjoy the film?

Beautiful woman: It was kind of out there for me.

You: Yeah, this filmmaker can be pretty wild, I guess he can be kind of an acquired taste. I’m pretty into film…how about you?

Beautiful woman: A bit, I guess. I really liked Rio 2.

You: You like animated films?

And so on. You’ve now moved from the general to the specific, but on terms that she cares about. She is more likely to be willing to contribute the effort required to make the connection now.

You might notice that in the both examples above, we had kind of a false start – we both saw the same movie, you enjoyed it, and it wasn’t her scene. What happened was that we started too specifically (which, of course, was natural – it would be weird to walk out of a movie and ask “uh, do you like movies?”). The fix is to tack back to the general.

Pro-tip: As you can see, I prefer going straight for the handshake. It’s a little bold, but it prevents you from starting with a line that will turn her off. If it feels too bold for the situation, you can save it for later.

Bonus pro-tip: This is a tough one to pull off, but if some time has passed, and you’re feeling a connection, you can storm the castle with:

“So we’ve talked about your job, your x and your y…what are you really passionate about?”

The big risk here is that she’s really passionate about her job, x or y, and you’ve missed that, and it comes off as dismissive. But if it works, it works big. Don’t even consider using this until the second hour of conversation.

SLAYING NEEDINESS

There’s a great line in the movie Broadcast News where a lonely man asks “Wouldn’t this be a great world if insecurity and desperation made us more attractive?”

It’s a powerful observation because it illuminates the nature of what psychologists call “social proof”. A financial corollary to this is “banks only lend money to people who can afford to pay it back”. If we enter into a conversation sending the message that we desperately need to connect (even though we do – every single one of us, though maybe not at the same moment), this is a sign to others that we have trouble connecting. So while our need to connect is true, that time when we’re forging that fragile first connection is not the time to share it.

Just as you move from the general to the specific, share yourself in the same way, a piece at a time. Treat your vulnerability as a prize that she has to earn, just as you have to earn hers. Don’t, unless the social context emphasizes (and maybe not, even then) talk about politics or religion. Don’t spill your heart out to her in the first ten minutes you meet her – that part of your self is too valuable to be traded so coarsely. Treat the interaction as an opportunity to explore whether, when and how much of yourself you’re going to share.

PLAY IT SMART

A lot of communication with a woman is non-verbal. If she’s wearing headphones, if she’s talking on the phone, if she’s in the middle of a conversation with a friend, it’s probably not the right moment. If you’re nervous, you will tend to speak more and faster than you would ordinarily…slow down, and allow there to be space in the conversation. A pause need not be an awkward one, and it can give her the opportunity to contribute energy to the interaction.

Finally, if the connection just doesn’t happen, conclude the conversation gracefully and count the interaction as a skill-development exercise. Keep in mind that a woman can be socially awkward (or downright rude) in how she handles this – just let it go. You don’t need to set her straight – you don’t need anything more from her. Here are sample conclusions in ascending order of terseness:

Her: Well, I’ve got to get going.

You: It’s been a pleasure talking with you. Have a nice night.

 

Her: I’m sorry, but I’m dating someone…

You: Fair enough. It’s been nice talking with you.

 

OR, if you didn’t have any romantic intentions:

You: I’m sorry, I didn’t mean to give you that impression. I won’t take up any more of your time.

Her: Who the hell are you anyway? My boyfriend is going to…

You: (chuckle) Goodbye.

The key takeaway here is that there is no “zinger”, no snappy insult. Who cares? The ultimate victory is to not need to salvage your wounded pride. Even if it’s not true, even if your pride IS wounded – the most graceful, elegant way to handle it is as if it weren’t.

Pro-tip: Eye contact is a thin line between connection and coming off as a staring psychopath! Look into her eyes long enough to make a note of their color of her eyes, a second or two, and then feel free to unlock.

SPEAKING WITH HEARTFULNESS

Everything I’ve talked about so far has been relentlessly tactical, so we need to step back for a moment and recognize that we’re employing these tactics for the higher purpose of actually establishing the connection. That is to say, we’re not trying to manipulate her, we’re trying to find what it is that we share, and what of ourselves we can share with each other.

A man, once married, instantly becomes better at talking to women, I think. It’s tempting to attribute this to simply having the pressure off, but it’s more complicated than that. The most important thing is that now the man (assuming that he’s a decent and honorable man) has no agenda. The reason why a married man can do this better is that he’s not carrying the additional emotional baggage of trying to get something from the woman.

Have you ever had the experience of slowly realizing that the person you’re talking to is not at all interested in the conversation, but is trying to sell you something? How did that make you feel? No one likes to feel that they’re being manipulated, or being used.

FOCUSING ON HER

A big mistake that men make is trying to impress. Of course you want to impress the woman, but it has to happen organically – if you reel off your resume (or worse, your bank balance), you’ll either fail catastrophically or connect in a problematic way. The key is to try and keep the focus on her. The number one thing that you need to communicate is that you’re interested in her.

You might ask, “didn’t I communicate that by walking over to talk to her?” Not at all – you might be interested only in yourself, and merely using her as a platform for that. You might be interested only in going to bed with her. You might be interested in using her to get over your last girlfriend. It’s complicated – women pick up baggage the same way that we do.

Imaging the coolest, most interesting person you can think of, living or dead – and imagine the general flow of the conversation. How much would you want to talk about yourself, and how much would you want to talk about that person? If I were to have cigars with Winston Churchill, he would leave knowing next to nothing about me.

Pro-tip: don’t take this too far and rebuff a question – remember that this isn’t an interrogation; it’s an attempt to connect. It’s all about energy – share enough of yourself to connect, and focus on learning about her.

On the eve of the election in Great Britain in 1886, a woman dined with the two men vying for the post of Prime Minister, William Gladstone and Benjamin Disraeli. When asked her appraisal of the men, she replied, “After dining with Mr. Gladstone, I thought he was the cleverest person in England.  But after dining with Mr. Disraeli, I thought I was the cleverest person in England.” Which would you rather be?

BEAUTIFUL WOMEN

Some parting words on the subject – every woman is beautiful. Lest you think that this is greeting card blather, let me illustrate it for you.

I held my grandmother the day before she died. The next day, I was looking through a photo album of hers, and saw her whole life laid out– when she was a young bride, living in Pyote, Texas, then older with her children, then shortly after my grandfather died. I looked across these pictures, and saw a picture of her holding me when I was about three years old. In them I could see all of her dreams, loves, trials and disappointments. I could see the whole truth about her, and it was beautiful.

I love my mother, wife, and daughters better than I love a stranger because I know the truth about them more perfectly. Our love for our families doesn’t come from blood, it comes from knowledge – from having moved past the shallow to the profound, from having shared pain.

Every woman is a wife, daughter, mother, sister, lover, and friend. Every woman is beautiful if you have the eyes to see the truth about her. This is the task that lies before you as a gentle man: to learn the truth about her, and communicate to her that it’s safe for her to share it with you.

If you found this post helpful, you’ll probably also like our FREE webinar on Dating Confidence for Men. Click here to get access to the webinar.

Chris B. Behrens specializes in social skills and refined living for men who are striving to be morally straight. Chris is a musician and competitive ballroom dancer and lives in Fort Worth, Texas with his wife and six children.