”Vincent in Boston” wrote in to ask:
“Seth, I saw the most incredible girl on the T (subway/metro) this evening. She had the greatest vibe. It wasn’t just that she was hot. Even the way she sorta-danced to the music (I assume) playing through her earphones had me hooked. How can I talk to women like that? I’m an okay-looking dude, but it’s not like women flock to me. I’m good at talking once I’m started. I just don’t know how to start random conversations with women I’d love nothing more than to talk to. Help me out, bro!”
(Ladies, this will work for you, too. Just translate genders as-needed)
First off, Vincent, I know the exact feeling! It’s hard enough to build up the courage to walk up and say something to a beautiful woman without the added pressure of thinking she’s going to shoot you down immediately. And yet, most of us can recall a time or two when exactly that happened.
Why do you fail when we try to talk to women? We fail because we’re trained to start conversations based on shared interests, common values, and circumstances. This training puts us on a path to failure because it forces us to make assumptions about complete strangers. It’s no wonder we get negative responses when we try to connect based on those assumptions. Nobody likes being put in a box! After multiple failures, we start believing that there’s a problem with us when the real problem is with the technique. Consider these examples of common failures: (we’ll use the name “Meghan” for the sake of example)
- Meghan is wearing a Yankees baseball cap. Vincent says, “Hey, I like the Yankees, too. Imagine that!” – (Assuming a common interest) – She might not like the Yankees or even baseball for that matter. Vincent would do just as well to state the color of her shoes, Captain Obvious. On top of that, ending a “first sentence” with anything but a question mark spells failure.
- Meghan is standing in line at micro-brand coffee shop. Vincent will probably try, “So, you’re a fan of fair trade products too?” – (Assuming a shared value) – A lot of people frequent small coffee shops because the 8am lines at Starbucks are too long. Vincent improves by asking a question but there’s still an assumption. Conversation is dead. Ceased to exist.
- Meghan is standing next to Vincent on a crowded public transit car. Things couldn’t be better for Vincent. He has a captive audience. But what will he say? We can expect him to make a comment on the the weather, the crowded car, or the rising cost of transportation (Circumstance). Meghan will probably reply, at best, or grimace and turn away, at worst.
Sound like something you’ve experienced before? Perhaps it sounds like you? The important thing is to recognize the problem, understand the past, and think smart about the future.
Here’s one way to start a conversation with any woman, any place:
Step 1 – Create A Context
Start your conversation with a question that requires a substantial answer. Check your question against the following test before trying it on Meghan.
- Is the question crowd-friendly? (Avoid topics like Family planning, animal testing, most political topics)
- Does the question invite multiple responses? (“Do you like the color red”=fail, “What should I buy my Mom for Mother’s Day”=WIN)
- Do I have a follow-up question in mind? (If the first question fails, do you have a back-up topic?)
Just like American Idol, if you get three yes’s, you’re going to Hollywood! Once you have your question in mind, look for a lead-in. An excuse, if you will, to ask your question. If nothing comes immediately to mind, just introduce yourself and jump right into the question.
Mother’s day is upon us. (Ladies, you can use this for Father’s day) That means that today is THE perfect day for you to try this technique out. How? Spot an attractive and sober female. (If you don’t like females, translate) Walk up to her and create the context by leading into your question.
“Hi, I’m Seth. (Move along quickly) I couldn’t help but notice you’ve got a cool sense of style.”
(She knows what my name is and I’ve given her an easy compliment. If she doesn’t want to like me by now, she’s at least ready to listen.)
Step 2 – Call For Help
Follow your lead-in by requesting her help with something easy and friendly. (Picking out lingerie=fail, buying presents for relatives=win)
“Tomorrow is Mother’s Day and I’m not sure what to get my mom. She’s a cool lady but I have no idea what to get for somebody who has everything already. What would you recommend?”
What is your underlying statement? You’re aware of the holiday, you appreciate your mom but aren’t codependent, and you’re willing to ask for help. (These are all wins, good job!)
(Meghan will, if she’s not late for an appointment and you’ve showered recently, give you some advice on what to get your mom.) You’ve successfully navigated a postive interaction with Meghan. Now what?
Step 3 – Follow Through
Express thanks for the help and cut away to another topic. The conversation is started, now’s your time to follow up with things that interest you besides cleavage (Don’t stare). If you see Meghan regularly (perhaps you travel the same way to work, get coffee at the same place, etc), cut away as soon as she gives you the advice. Why? Because you’ll be leaving with your next conversation ready to go! The next time you run into Meghan you’ll be locked and loaded with an update on how the thing she helped you with turned out.
“Hey, (make sure you get her name and remember it for next time, we’ll go over some tricks for this soon)! Thanks for the help. You made me look really, really good. My mom said she liked [suggested gift/action] so much that she’d forgive me for stealing the car when I was 12!”
Meghan laughs. She likes that you remember her name (REALLY likes it) and asks about what you stole the car for.
Look at you. You’re having a conversation with a beautiful woman who might just rock your world.
Good luck, Vincent! (Ladies, this will work just as well for you.) Give it a try and let me know how things work out!
When was the last time you assumed something about a stranger only to be proven entirely wrong? Drop me a comment with your story!
photo: mfr
Finally a new article on my favorite site.. for your question on experience, I am the type who never assumes most specially if it involves a stranger and most specially someone I think I would be attracted to.
But i love your tips. The hardest part with meeting someone new is striking a conversation. You never know what the reaction might be. For instance, me.. people would always assume that i was unfriendly, or intimidating and never really try to talk with me. But for those who had the courage, found out that i was really a very easy person to speak with. I love meeting new people. My advise would be smile more (but not to the point that they would think you were nuts) and just do it. You will never know unless you try right?!?!
great post..
Hi Misty!
I’m sorry. I know it’s been awhile. Needed to make sure it was something I’m fully behind. Obviously, I decided in favor. =)
Yes, I agree about striking the conversation. That’s why I say bite the bullet and go in guns blazing! (perhaps too many firearm references). Really, the conversation I included has happened for me in many variations. People respond very well to friendly conversational advances.
It’s easy to forget that nearly everyone else is just as afraid of being rejected as we are. Glad to be back! =)
It is a mission – it requires preparation, anticipation. They are called lines for a reason – they work, but they are not just a line. A relationship, especially the start of one– is a dance.
Sometimes you lead, sometimes you follow. When it becomes less awkward, and the conversation flows, then you get to see where the dance takes you.
When you are sitting home smoking a cigar and the lady is with you, then you know the next dance is promised.
@Terry
You had me until the cigars. I suppose that’s a sign of loyalty/tolerance though? The ladies who don’t mind cigars seem few and far between in these parts. Then again, I don’t have the Hemingwayesque looks to go with the cigar. Perhaps someday?
We shall see.
The conversation intro isn’t a line so much as a system, I think. Just like we get into the habit of starting letters with the same line or using the same words to say farewell on the phone, I think we can build good conversation habits that encourage responsiveness instead of cold rejection.
You’re right. It is a dance!
It is a sign that someone accepts you – for whatever faults you have.
The line is old, but it can begin the dance. A system is good – but it begins a dance. One is more sophisticated. Responsiveness comes from genuine interest in the other person – whether you date, or talk, or tweet.
Rejection – instant rejection is like a bit of rain – you shake it off and move on. Rejection after a while – that is like pneumonia, takes a bit longer to get over, and you need a bit of help to get over it.
Good tips, Seth. As a single gal I thought I might share a little of my own experiences on the subject of pickup line do’s and dont’s:
First, here are a few things that can be complete deal-breakers no matter how good the “line” is.
1. Staring at boobs. Don’t do it. Ever.
2. You start talking to a girl. And then – no matter her reaction – your eyes wander over to another woman. This demonstrates that you are guilty of having one of the least attractive male syndromes – namely, “the grass is always greener.”
3. You make sure a girl sees your car. This happens often in LA. #fail.
Now for the good news:
1. Confidence goes along way. Guys who are secure with themselves can really go far no matter their other, perceived shortcomings.
2. Be genuine. No matter how well-crafted, if a “line” comes off as disingenuous, you’re on a doomed mission. A smart woman will know the differece between a guy who’s sincerely noticing something special about her and a guy who simply wants to get laid this weekend.
3. The whole concept of “the pickup” gives you an opportunity to showcase some important skills: a) that you can think on your feet, b) that you’re willing to take a risk, and 3) that you can move on if things don’t go your way. This is a trifecta of positive qualities that just might make a girl think twice about you.
If you aren’t the most confident of guys, remember, “fake it till you make it.” Do it well, and no one will know the difference. But for the love of god, please don’t cross-over into the dreaded land of arrogance.
Hope this helps
Every good guy deserves a chance.
@Terry – I like that. “Instant rejection is like rain”…which rather makes the argument that we should let people know where they stand as soon as possible. It’s what I try to do!
@LC – Awesome! I like the 2nd#3, #6? Hmmm. Anyhow, yes. Some people say “ooh, that’s picking up somebody. not cool” and they forget that there’s a difference between learning how to start conversations and seeking techniques to prey on the emotionally fragile.
Genuine wins all the way. The “pick-up-artists” have soiled the concept but the basic vocabulary remains the same. We’re all just trying to meet somebody who spends more time making us happy than making us miserable. It’s the finding of that person that really makes for an adventure.
Thanks for swinging by with some great thoughts. I hope you’re healing and feeling better!
Great post! I found you via twitter, and like your blog. As a single woman, I’d have to say you’re right on… this approach would definitely work for me!
This is great advice. But I’m obviously having trouble substituting in other questions for the same type of result. How would this work on any day other than the day before Mother’s Day (or someone’s birthday… Christmas)? I guess I’m wondering if you can give an example of a good conversation starter that doesn’t revolve around asking someone for advice on what to buy for someone else.
@Jan – Thanks! Just hit you back. Deep stuff on your blog, missy!
@Laura – It’s not entirely obvious to me, no. You never need advice on anything?
Think of it this way. If you had an amazing and talented SigOt, what sort of things would you ask for advice on? Probably just about everything.
This technique is actually enough to take care of most people by itself. I buy things at least bi-weekly and feel compelled to have conversations with certain strangers at a lesser frequency…and I’m a friendly dude. If this were the only technique I used to start conversations, I could get by pretty well.
Most of the “other” questions you’re feeling tempted to put into the “slot” in this process probably make assumptions about the person you’re talking to.
The whole idea is to avoid making assumptions at first. You walk in with an open mind and you’ve a better chance of walking away with a full heart.
Does that make sense?
Confidence~humor~intelligence combo works very well for me and vice versa. And if all else fails, I take out the ping pong balls from my pocket! :~)
Excellent concrete suggestions, Seth! Thank you!:~)
Yes, that makes sense. And I am so using that tip when I go laptop shopping in a couple weeks because oh my heck, I need advice from someone other than the sales dude on commission anyway, and hey it wouldn’t hurt if it came from a nice looking guy
Exactly!
The site looks different. I like it! Good dating advice Seth. I’m glad someone gives dating advice because we all know that I don’t. I’ll try your suggestions next time I see an attractive potential male suitor. Speaking of which… I heard Mark Wahlberg is in town. I should track him down and practice.
I found this blog really interesting. My field requires that I ask a lot of questions designed to pull information that is sometimes perceived as sintrusive. However, it's not to hard to do and also applies to starting conversations that lead to longer ones.
People enjoy sharing meaning together and one way this is done is through conversation. The types of questions and responses you use make all the difference.
There's a great book by Bianca Cody Murphy from Wheaton College called Interviewing in Action. Naturally, you aren't traditionally interviewing this person, but you are trying to share information, and that is indeed a type of interviewing. However, you want the conversation to go back and forth. Deborah Fine, talks about this on her CD The Fine Art of Small Talk. She talks about a situation where Oprah had people try to start dating conversations based on phrases given by the audience.
Combining the book with the experience from the CD, we got something like this.
What's your sign? (moan, oh gosh, this is going to hell–it's also a closed ended questions, the type that gives a one word answer, such as "yes" or "no", most of the time.)
"Pisces." (You can almost hear the horns of the Titanic and the screams of a conversations going down in flames…This guy was smart–or lucky).
"Pisces?" (This could be called a simple reflection, repeating one word to get someone to elaborate more).
"Yes, Pisces, what's yours?" (Another close ended question–this conversation is tottering, but wait…)
The guy then tells the woman his sign. She, then manages to break the ice with a different type of question.
"Oh, what are some of the aspects of that sign?"
BOOM. They are off and running. The woman has asked an open ended question, one that requires elaboration.
At the end, she could paraphrase and summarize, saying something like, "oh, so your saying that sign tends to be happy-go-lucky, chance taking, etc or whatever else she thought she heard. He could always follow up with a question about the aspects of her sign.
Thus a really dull, almost predictably over-the-top question turned into a conversation with shared meaning.
As mentioned earlier, the back and forth nature is also very important; it is also important to show that you are interacting and understanding the conversation, thus the feedback, summarizing, and paraphrasing.
It's really cool when someone says, "Wow! You understand me exactly!" I get a lot using these techniques. Applied appropriately and conservatively, they are great ways to get any type of relationship, especially a potential first date, off the ground….
Good one, Seth. I can’t help but imagine a woman thinking you were implying that they were old, though – if you asked them what you should be getting for your mother for mother’s day
These tips translate well into the online dating world, too; but fortunately there is more to work with there. Just look for something in their profile that interests you, and send them a message about it. Questions like you described also work well in this case.