3 Steps To Starting Successful Conversations

 ”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)

1. 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. 
2. 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.
3. 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