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But even assuming you've conquered approach anxiety with a big, heavy hammer (and if you haven't, see yesterday's newsletter) there are some situations that can make even the most seasoned veteran scratch his head and go, "Now what?"
Well, by now you know I'm all about eliminating the phrase "now what?" from our collective vocabulary.
Until that day finally gets here, however, here are some practical suggestions--rapid-fire style, mind you--for meeting a woman you just have to talk to, regardless of how sticky the situation is.
How about a "top ten list"?
Here are the first five this time around. Bear in mind that challenging situations WILL typically require bold action:
1) She's Walking The Opposite Way Down A City Street
In a scenarios like this, you've got to be pragmatic...and you've got to be fast. There's no time for thinking, just action.
If ever the "three second rule" is particularly mission-critical, it's under circumstances such as this.
So call it out like it is.
Approach the woman from an angle where she can see you, tap her on the shoulder and pronounce--bluntly--"Look, I saw you and I knew I HAD to meet you. You're obviously headed somewhere and so am I, so give me your number so we can continue this conversation properly later."
First of all, you'll be shocked by how frequently your sheer confidence turns a woman on in situations such as this. Second of all, you'd better have something to write with. There's no time for trifling with cell phones, etc. Write her number on your hand.
2) She Has Headphones On
Oftentimes we automatically assume that a woman has headphones on at the gym, beach or wherever to "tune us out". You're probably right.
But all you need to remember is that women are hard-wired to follow our lead, and they are NOT hard-wired to their smartphones.
Again, approach from an angle that won't seem like she's being ambushed, get eye contact with her--even if you have to get right in front of her face to face (at least 18" away, please)--and simply tap your ear.
That's the universal symbol for, "Would you please remove your earphones?"
Prepare to be shocked by how consistently this works. And when she loses the headsets, also be prepared to introduce yourself. As always, your confidence will be credited to you by any woman with her head screwed on straight.
That is, unless you're flat-out creepy, or something--which you're not.
3) She's On The Phone
The first step here is to relax. You do not have to solve "world peace" within the next thirty seconds (let alone abide by some weird "three second rule").
If you don't have anywhere to be for the next few minutes, you'll be pleasantly surprised by how seldom women's phone calls really last the eternity that stereotype would lead you to believe.
And when she hangs up, simply walk up to her with a smile and tell her that you'd like to make friends with her, but only because it's obvious she must already know how to make friends pretty
easily...considering that she was making such good use of her phone.
By the way, the longer she was on the phone, the better this works, so don't sweat it.
So what if her phone call seems interminable? Well there's no two ways about it: You're going to have to grow a pair.
Position yourself in front of her and start shaking your head subtly while hopefully making eye contact with her. We all as humans are naturally curious, so chances are excellent that she'll interrupt her phone conversation to acknowledge you.
At that point, you simply say, "You know, I saw you from across the room and knew I had to meet you. But from the looks of things, you've got lots of friends already. And I'm pretty spoiled...I'm used to being top priority." Then make sure to crack a sly smile after the mandatory couple of seconds.
If she doesn't love you for this--and hang up in homage to your sheer courage--then you had no chance anyway, and are probably better off. Trust me on that.
4) She's On Public Transportation
This is one I get asked about a lot. Whether on a subway or on the bus, the first thing to remember is that you are BOTH in the same boat (perhaps literally), so now is NOT the time to get self-conscious because you don't have a car or something.
On the other hand, what it IS time to do is move with a quickness. You have no idea when her stop is coming, so you've got to assume that you only have thirty seconds MAX.
So you've got to address her directly. Tell her you weren't about to let this ride you are on together pass you by without at least meeting her. Get her number and tell her what time you'll call her.
A situation such as this is to be treated much like when you encounter a woman walking in the opposite direction on a city street.
5) There Are Lots Of People Around
This is a particularly deceptive situation, isn't it?
Frankly, I think most of us are WAY, WAY too narcissistic when it comes to meeting women when a lot of other people are around.
We tend to automatically assume that everyone else is going to key in on the situation and any communication you have with the woman is likely to make a scene.
Well, let me introduce you to a slice of reality. Most people around you aren't going to give a rat's hind parts what's going on.
Seriously.
First of all, they've got to be within earshot enough to hear. Then, they've got to have the presence of mind that you're creating a "movie moment" with a cutie.
THEN...they STILL have to CARE, which like I said is unlikely.
Most of the time, any woman out there will be proud to have the story to tell her girlfriends about how a man like you "picked her out of a crowd" and chose to meet her, without any regard for who was watching.
Play it cool, make normal conversation and I all but promise you that few, if any, people will even notice.
And what if they do?
What if some blue-haired grandma gives you a wink and a "thumbs up". Smile back and proceed. If anything, the woman you've just met will be even more intrigued by the way you handle yourself with "compassionate confidence".
Ha. You didn't know I was such a crazy mofo, did you?
Actually, situations such as these can be flat-out FUN to challenge yourself with.
I mean, sometimes I even strike up conversations with people in challenging situations like these just to remind myself of how stunningly possible it really is.
Let me tell you, most of the time I let the guys who claim to be "pickup artists" do all the heavy lifting when it comes to this sort of thing.
6) You've Got Very Little Time To Work With
The modern world is a busy one, so the chances are actually better than not that you'll have a very limited window of opportunity when it's time to meet a woman.
Beyond spotting a woman walking the other way on a busy street or on the train, like we talked about last time, you may notice a woman while waiting in line. She may even be the one helping you when it's your turn.
Or you may be finding your seat at a sports event, or running to catch a plane at LAX.
Or you may be on a business lunch and see her at another table, when you just can't justify time for anything more than excusing yourself to the restroom.
The situation doesn't matter. The procedure is the same.
You approach the woman in plain view, and confidently (as in audibly, without yelling) get her attention--even by just saying, "excuse me."
And because you are approaching her without startling her, you demonstrate that you know how to make her feel safe in your presence.
So how do you demonstrate character when time is limited?
That's the most powerful part.
When you begin to speak to her you lead with exactly why you don't have time to talk, and that you're committed to what's going on elsewhere.
For example, "I'm actually at lunch with a client right now and only have a moment, but I wanted to meet you."
If it's flat-out obvious why you have no time, you only modify the statement slightly: "Obviously, there's people in line behind me and time is short."
Then you tell her your name, to which she'll likely respond with hers.
Having established that there's no time to work with, you tell her that it would be great to get her number so you can call her later when things aren't so rushed / under more casual circumstances / etc., at whichever time you tell her you will.
Importantly, do not ask her for her number.
Confidently suggest she give it to you because you don't have time to deal with her playing coy about it, and especially because your leadership is far sexier to her than uncertainty or sheepishness.
You'll be amazed at how often this works for you. And even if it doesn't, you won't have to live with the regret of having given up before you even attempted.
7) She's With Friends
This is one that guys get completely crossed-up over, isn't it?
I think the biggest mistake we make when we want to meet a woman who is with friends is that we single her out from the crowd too early.
This comes off as self-serving and even a bit pushy. It's anti-social no matter how you slice it.
Recall what I explained about the "big four" above. While it takes inherent confidence to approach a group of women, it takes a "big four" man to help everyone in the group feel comfortable with your presence.
So the idea here is to address everyone in the group, all while making it obvious that your presence is temporary.
In other words, you don't want to come off as trying to encroach upon their territory (presumably because you don't have any friends of your own).
The best way, then, to do this right is to have a real, actual purpose for talking to them.
One time when we were doing a podcast that involved getting women's thoughts on a particular topic, I approached a table full of women and told them (as opposed to asking demurely) that I valued their thoughts regarding a certain question.
Then, with voice recorder in hand, I asked each respective woman the question and bantered with her individually to the delight of the others.
I knew immediately when a woman was enjoying the conversation I was having with her. After all, the whole point of approaching women is to start a conversation, right?
I was already with Emily at the time, of course, but from there it would have been easy to suggest that more conversation continue later...and I bet the other women would have suggested that she "go for it".
By the way, contrast this strategy with that of using a thinly veiled "opinion opener".
8) She's With Her Mom
Meeting the parents is a high-stress event that by all rights should take place sometime after you've been out with a woman at least a few times, correct?
Well, what if she's out with her Mom (or her Mom and Dad!) when you spot her?
For sure, you could adapt what I suggested above in the seventh example to this situation as well (as you could for #9 below also, by the way).
But I'm not an unreasonable man.
Asking you to boldly approach a woman who's sitting with her parents is such high-end, advanced stuff that if you can pull yourself together to do it you probably should be writing dating advice of your own.
So hey, by all means if you want to position yourself so that you can make eye contact with only her and not the 'rents--and then give her a look that says, "Hey, I'll meet you over there", then go for it.
Or if you want to wait until she inevitably excuses herself to the ladies' room, I understand. That could work for you also.
But guess what? Trying to avoid the parents could actually end up being more awkward than actually sacking up and approaching.
See what I mean?
So...can you pull it together and actually do this?
Here's how to make it way easier on yourself.
First, don't assume what the relationships are.
Allow yourself the slightest extra measure of "politeness" than you might usually approach with (the woman will credit this to you as "decorum", given her parents are around), excuse yourself for interrupting them, and ask how they know each other.
When it's established there really are parents involved, acknowledge that you figured that might be the case and introduce yourself to both (or all three).
Then...the magic starts. Briefly smile at the attractive woman with the world's slightest expression of "watch this", and talk to the parent(s).
Explain that you realize they're spending family time together, but that you couldn't help but notice that her/their daughter lights up the room.
Next, turn and talk to the woman. Assure her, with a light laugh, that you're the kind of man who knows how to respect a woman and that you think her parents would approve of you, so you'd like to speak to her later.
Then get her number.
And don't be surprised when her Mom (and maybe even her Dad also) encourage her to go ahead.
I've personally watched this happen with breathtaking effect and heard even more stories of similar results.
One time my own sister was approached by a waiter at a restaurant with both my Mom and Dad at the table. Even my little brother was there, if I remember correctly.
I think my Mom still talks about how amazing that "movie moment" was...even to her. I personally wasn't there, but I'd love to have seen it.
Parents want the best for their daughters. You are not unwelcome in their daughter's life unless you deserve not to be welcomed.
Might you encounter a psycho parent along the way? Perhaps. But then again, you might encounter the world's most effective wing instead.
9) She's With A Guy
In many ways, this can be even more potentially intimidating than when a woman is with her parents.
But again, the secret is you don't have to commit to being romantically interested in her right away.
The most overlooked strategy here--which should have been obvious when you think about it--is to observe for a full minute or so before rushing in.
First off, look for wedding rings if you're in a position to do so without being weird about it.
If they're married, back off. I'm not in the business of teaching "Marriage Destroyer Game"(tm) here.
Next, watch the interaction between them.
What is their body language like? Is she showing the signs of attraction that you've read about 100 times? Or are they clearly presenting themselves as "business-like"?
Does he seem "like a brother to her"? Is "JBF Zone" written all over this situation? If that's the case, he might actually be her brother...which would be as good to know as if he's her boyfriend or husband.
So as discussed in example #7 above, if it seems like the right thing to do after a bit of "recon", approach with some purpose and assume they're boyfriend/girlfriend. That's the single best way to get a bona-fide read on the situation really fast
Blatant laughter with a quick note of correction on their part will be a great sign.
Watch carefully to see if one of the two is more adamant about establishing that they're not a couple. If so, handle the other person with care.
In other words, if the woman looks hurt when the guy says they're not a couple, you've got "politics" on your hand. If the other way around, then he may get a bit jealous if you proceed.
You've got to look alive out there.
But if there's no romantic intent at all between them, you may say to the man, "And I was just about to congratulate you for being such a lucky guy."
Then wait, and listen to what she says to that. Look for any positive response, up to an including, "Nope. Some other guy's going to have to be the lucky one."
Money.
10) She's Clearly Not In A Great State Of Mind
Women are emotional creatures, aren't they? Sometimes you'll see a woman who's attractive for sure, but isn't exactly in a happy-go-lucky mood at the moment.
This doesn't necessarily mean you have to abandon all hope of meeting her.
If she simply looks slightly to moderately sad, peeved or frustrated; you can approach her in plain view and say, "Hey...it can't be that bad." Any other similar statement is fine, "You know, this too shall pass."
The golden part of what happens next is that you'll be given everything you need to know about whether this is a high quality woman or otherwise.
If she snaps at you, ignores you or treats you poorly in any other way after you've clearly taken the lead to lighten things up for her, then consider that a major plus. You've found out way earlier than most guys would have that she's dead wrong for you.
But on the other hand, what if you succeed at bringing a smile back to her face?
Congratulations...you've just led in a way that establishes an amazing first impression of you in her mind. She'll tell that story to every one of her friends.
And by the way, you'll have also set a rock solid precedent in the relationship management department, assuming you'd like to keep her around after your first date together.
Oh, and if she's stark raving mad, berserk and/or crying her eyes out? That's when you should stay away instead...at least until she has simmered down to "slightly to moderately" emotional.
So there you have it. That's ten sticky scenarios that you'll be better equipped to handle, should any of them apply the next time you see a great woman you want to meet.
So my challenge to you is to take at least two examples out of the list I've offered above and by all means put them to the test this week.
What did I miss? Leave it in the comments.