10 Tips for Talking to Ladies & Gentlemen.

Via Waylon Lewis
on Mar 28, 2012
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The Non-Douchebag’s Guide to Getting Laid.

(For Ladies & Gentlemen)

Are you a lady, and too-often too shy to talk to that cute stranger (lady or gent)?

Are you a gentleman, and too-often too shy to talk to that cute stranger (gent or lady)?

Are you too tasteful to read books about the Game or the Art of Seduction?

Are you too self-respecting to join a dating site?

Are you too decent and kind to be a douchebag, and just sleaze your way into that cute wo/man’s life?

Well now there’s help!

elephantjournal.com is your home for Nice People who Don’t Have to Lose.


Here’s my painstakingly compiled Tips for (Wo)manning up and Talking to that Total Stranger.

1. First of all, let’s stop comparing our (lack of) success to that of players. We don’t want to be a player, a douchebag, that sleazy guy (or girl) who’s always pushing his or her self on everyone. We don’t want success without authenticity. We want both. Because it’s only those real, connected, fun, genuine connections that are more than a complete waste of time. So next time you see player on a date with a hot girl or guy, feel sorry for both parties, and move on.

2. Take care of yourself. If we don’t 1) meditate in the morning, 2) dress well (or simply, or stylishly, which isn’t always the same thing), 3) exercise, we may not be that desirable, present, or confident. Take care of your body and mind in the way you’d hope that whomever you want to be with takes care of their self. Too often friends complain about being lonely, but do little to make themselves confident and attractive and sane. If you actually want to be with that somebody, get yourself to the meditation cushion, the gym, on a bike, to the climbing gym or yoga class. And buy some clothes that make you feel elegant, fun, you. I recommend secondhand shops for stylee and affordable (and eco) clothes that have character—character will help you break the ice…

3. I have just about no idea how to talk to random women (or in your case, perhaps men) I don’t know. I would, instead, encourage focusing on community. Where do you hang out, spend time? What are your interests? If you’re well known in a particular community—parties/barbeques, dancing, riding horses, school, an open mic night…meeting people, being introduced to people will just happen. And then, while you may not know that cute somebody, at least you’re be one degree more familiar, “safer.” So forget that random cutee you see in the grocery store, and get more involved and active in your own life. Then, meeting people might just happen (of course, this is coming from a guy who has been alone for most of the last three years—and one of the two meaningful relationships I did have was, by a factor of 1,000, the worst I’ve ever had in my life. The other one was wonderful.)

4. What’s that? You want to know how to talk to that lady/gent you see in line in the park, at the cafe/or at the grocery, anyway? Well, obviously, do 1) and 2). If you have, then, the main thing is to just breathe deep and go for it. As Buddhists say, have confidence to go beyond hesitation. Bravery, even awkward bravery—is attractive, or at least cute. But if you’re so insecure you mess it all up, don’t worry, the worst—as my mom used to say, “It never hurts to ask,” in a different context—is that you’ll be right where you started. Alone. Failure isn’t anything to worry about. They may have a boy/girlfriend. They may not be in a place to be interested. We have zero control over yes/no. All we can do is be ourselves and ask. If you do go for it, just keep it simple. Say hello. Talk about something that’s happening—the weather, what he/she is wearing or doing, make fun of yourself. If you have friends or acquaintances around, talk to them first, slightly loudly but not too-loudly, first. Give him/her a chance to see that you’re safe and have friends and that they like you. Give him/her a chance to see that you’re decent, confident, and you know how to smile.

5. Speaking of alone, make friends with yourself. Do things you like to do on your own. Start enjoying being alone, and you’ll stop feeling ashamed about being alone. Maitri is key, here.

6. Get a dog. Not original, but effective. Dogs have a lot of energy. Dog have to pee. So that means no matter how you feel, how busy you are, how crappy the weather is, if you’re a decent dog-loving dog owner, you’ll have to go outside and get them tired. And outside, not in your room staring at your TV or laptop, is where we meet people. At the very least, outside is exercise and fresh air. That said, if you think your dog will be a “chick magnet,” you’re mistaken. Dogs are a magnet for chaos, generally. And chaos, as Trungpa Rinpoche says, should be regarded as extremely good news.

7. Don’t go for men/women based solely on looks. That might sound meaningful, but it’s not. Be hyper-critical of any weird vibes you get from someone: .00001 percent of people are craycray—bad news. Don’t be a sucker. If they are sane, it’s still not good to just chase looks. Remember beautiful men or women are just plain old humans inside, too. Don’t objectify based on looks. Keep it real and personal and human. Ignore looks, once you’re talking with someone, and just talk to them as a human being.

8. Beware the Friendzone. I “went out with” a girl for months, this winter. I put “going out with” in quotes because, though we went on “dates,” and “did various things together,” she rarely failed to fail to text or call or email or Facebook me back, promptly. She said she was interested in me, but her actions proved otherwise. If you find yourself adrift in friendland, call her/him on it. If you aren’t being treated with common courtesy, talk it over. If things don’t change, give up. Bow out gracefully, respectfully—and quickly. Life is short.

9. If you don’t like calling, don’t. Everyone out there will disagree with me on this, but I don’t see text or email or messaging as inferior to good ol’fashioned phone calls. I see phone calls as an imposition. You’re doing something, and suddenly your phone is ringing, bullying its way into your present moment. If, as Sun Tzu would agree, you’re most comfortable communicating in person or texting, do it. Play your game, not someone else’s rules.

10. Speaking of, let’s not play games. Be charming. Be coy. But be honest. If we feel a certain way, let’s just say so. If we want to go out to dinner with someone, let’s just invite them. Read fewer Top 10 Lists and skip the how-to books or videos. Let’s just do our thing. Be brave. Be silly. Go out there and make a little trouble. And remember: the journey is the goal. Our goal is not sex. Even if we think our goal is sex, our goal is not sex—because we will fail to reach that goal if we don’t walk the path every step of the way. Walking the path, in this context, means listening, talking, smiling. Simple things.

Let’s come back to the present moment, and ride it into Loveland. The present moment will get us “there.”


This is just a rough list off the top of my head. I’m the furthest thing from an authority you can imagine. If you have advice or tips for how to meet good folks and have genuine relationships, please contribute in comments below.

For more like this, “like” Sexy or Relationships.



Meet Cute under fire:

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About Waylon Lewis

Waylon Lewis, founder of elephant magazine, now elephantjournal.com & host of Walk the Talk Show with Waylon Lewis, is a 1st generation American Buddhist “Dharma Brat." Voted #1 in U.S. on twitter for #green two years running, Changemaker & Eco Ambassador by Treehugger, Green Hero by Discovery’s Planet Green, Best (!) Shameless Self-Promoter at Westword's Web Awards, Prominent Buddhist by Shambhala Sun, & 100 Most Influential People in Health & Fitness 2011 by "Greatist", Waylon is a mediocre climber, lazy yogi, 365-day bicycle commuter & best friend to Redford (his rescue hound). His aim: to bring the good news re: "the mindful life" beyond the choir & to all those who didn't know they gave a care. elephantjournal.com | His first book, Things I would like to do with You, is now available.


29 Responses to “10 Tips for Talking to Ladies & Gentlemen.”

  1. Richard La Rosa says:

    Great breakdown, Waylon. A comment on #10: Being honest is difficult, because most of us aren't even truly honest with ourselves. However, we can avoid the pitfalls of dishonesty by getting clear about what we want in our relationships and putting all our cards on the table. And, with that act, we need to completely let go of our expectations and wait for the alchemical reaction — whatever it will be. In doing this, we are able to separate ourselves from that siamese twin of dishonesty — withholding. Behaving at this level of honesty gives us the courage to express ourselves truthfully.

  2. Jessie says:

    awww Waylon, you slayer :* – mindful insights to live by while timing and synchronicity wait around the corner.

  3. Annie Ory says:

    OK first I want to be invited to a "barbequest"! That sounds just fabulous! If you tell me what exactly it is I'll even host one!

    Next I need to say, you're not "too self respecting" to join a dating site. You're just too judgmental and limited in your thinking. Lots of the coolest couples I know met on line. As a Dating Coach I wouldn't work with a client who refused to date on line. That level of resistance to a simple, sensible tool was evidence to me that they weren't ready for coaching, weren't really ready to move past the walls they'd constructed to keep love at a distance, as Rumi might have said.

    Where you totally nailed it is in asking them to get outside. I don't know where your soul mate is, but s/he isn't on the sofa in your living room. And seriously, you're dead on the money. So what if they say 'no'. You didn't lose anything you actually had anyway, so talk to people.

    Finally, a little trick from the Dating Coach: Social Cards. Yup, those old fashioned high touch purveyors of personal information. I ask my clients to make a card that has a photo of their face on the front with a first name and a non-work related email that does not contain your last name, a phone number with an outgoing message that doesn't say where you work or live or use your last name (for safety) and on the back, a photo of you doing something you love or that is meaningful to you, climbing a mountain, camping with your dog, running a marathon, dancing at a friend's wedding.

    I had many clients who met interesting and cool people they actually dated with these cards – which can be made on Kinko's website in 20 minutes and cost $25. They are fun and friendly ways, no pressure, to make contact in a public venue or to close a brief conversation without asking for a phone number. I have never had a client report a negative experience with them. I used them with great success when single, though I met my wonderful partner of 5 years on an Internet dating site. I once gave a card to a very nice looking guy in a bar. I was with my friends, he was with his, we'd exchanged a smile but I didn't want to intrude on his conversation or time with his people so I just handed it to him. A few weeks later he left a message on my phone. It said;
    "Hi, you gave me your card in X restaurant a few weeks ago. I just wanted to let you know, before I toss it (my wife might find it and think things she doesn't need to) that I held on to it for all this time because – well – it's been a while since a beautiful woman approached me in a bar. I'm faithful to my wife so it doesn't happen to me often, and your intentions were clearly honest, you didn't know I was married, and seeing the card in my desk every day just made me feel good. So thanks. And good luck in your search." So even if it's a miss, you can't hurt anyone by letting someone know you know think they're cool.

    I close with this. It's not self respecting to make up reasons why perfectly respectable venues for meeting cool people aren't "appropriate". It's just getting in your own way. So stop it. Use every avenue available to you, because that's what leads to success in any venture. You want this right? So go get it.

  4. I just go with the talk to everybody all the time and smile a lot approach. But then, I am also not trying to date and am pretty oblivious when men are attracted to me until one of them actually asks me out or asks for my number. Maybe we should go old school, Kindergarten-style: http://www.elephantjournal.com/2011/05/first-kiss… "I like you. Do you like me? Let's kiss." Keep it simple.

  5. elephantjournal says:

    "You're just too judgmental and narrow minded"



    PS: any barbeques I ever have, you're not only invited but expected to come by! ~ Way

  6. elephantjournal says:

    Hah. Sweet video.

  7. elephantjournal says:

    Thanks brother. "Self-deception" is the enemy—Chogyam Trungpa said something like that. We can uncover our self-restricting delusions through meditation, and cultivating honest, loving friends.

  8. Funny, insightful, daring and honest. Nice post!

    (Clark Gable: some boy for pulling faces! lol)

  9. Eric says:

    "The Tao of Way" ~ ( …tho' you take much better care of yourself than Dex 🙂

  10. Michelle says:

    simply awesome

  11. elephantjournal says:

    I don't know about insightful…the other day a beautiful woman and I ran into each other four times all over town. I finally said hello, we talked, she was friendly…and then I didn't know what to say, and said "have a good one!" and walked off. Real player.

  12. elephantjournal says:

    PS: here's what falling in love sounds like: http://www.elephantjournal.com/2012/03/a-song-to-… (ain't nobody that could sing like me)

  13. Chen says:

    Good advice for the introverted tech type. I have two roommates who don’t know their own potential, but they would be great with the good ladies if they just followed even half of this list

  14. catnipkiss says:

    If everyone is trying to "meet someone", WHY is it so freakin difficult to meet someone? – Alexa

  15. yogi tobye says:

    You're sooo money and you don't even know it.

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  20. Greg Eckard says:

    Thanks, Waylon! Wish I would have read this a week ago!

  21. faye says:

    having found myself back in the single's pool (after 8 yrs in the other pool, and in Germany, where, if you know it, has got to be the most challenging place to meet people) where we are all swimming around, crashing into one another, trying our best to avoid one another, or chasing one another, this i have learned: a. get to know yourself – it's worth it in so many ways (don't know how? do something, anything that freaks your poop) b. trust yourself (completing a. is helpful, though not necessary) and c. patience! make eye contact (but please don't stare – cannot tell you how many Germans have messed this up royally! – makes me wanna reach for my shot gun for protection) but don't hold major significance to it. just think, ok, cool, we've acknowledged one another. do not, i repeat, do not psych yourself out or what i call brain-fucking yourself. it's not fun despite the f-ing in it. then, employ the power of proximity and make your way to them, in your way. it could be directly walking to them or subtly and slowly. the point it is to be comfortable. again, even if go home alone you still have to sleep with yourself so refer back to a and b. and d. if at first you don't succeed, try again, yo. act as you feel, even if you don't feel ready. no one is ready – what does that mean anyway? you just have to start somewhere and if you have an open heart, -mind, and enjoy the ride, simply start where you are and learn the lessons along the way. get hurt? take a break, recupe and jump back in. lessons learned from middle school sports. fab xx

  22. Joe Elliott says:

    I think that meeting people is easy. But what about learning to trust your intuition and finding the will and the courage to follow through with it when it smacks against the fear of being alone or the fear of being trapped in a relationship.

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  26. click here says:

    This was the most bizarre meet-cute I've ever seen. So unnatural. Casual flirting during a fight for your lives?  No reaction to being shot? She hits him for no reason? It's just wierd.

  27. alen owen says:

    What an eye opener….the tips are awesome can’t wait to practice them

  28. Billy says:

    The way I feel is, do what ever it is you Love to do and in doing so you will find some one to make a connection with, and a connection is a great start.

  29. Aly says:

    This sounds like such great advice! I met my soulmate online, actually on fb by accident, but it goes to show you that your soulmate may not be in the same town as you. He at the time lived in San Antonio and I in Houston. I shall be referring my single friends to this good advice, since I never have any!