How to Maintain Conversations with Women?

For over two years, I’ve had clients and the general population of men ask me the same question when it comes to talking to a woman.

“What do I say next?”

For many men, it’s a serious problem because not knowing what to say will inevitably lead to a whole lot of silence, even more awkwardness and an end to what could have been an amazing conversation with a really attractive woman. Some guys are becoming more and more comfortable with approaching and starting conversations with women and then they hit this roadblock.

“Ok, so I approached her and I got her to smile. She gave me her name and now she knows mine. Now what?”

Well, to really understand the answer, we have to really look into a couple myths and squash them once and for all.

Awkward silence is NOT awkward. Men (and even women) have this belief that silence in a conversation is a bad thing and feel compelled to fill it in with SOMETHING. I am here to tell you that it is NOT true. When two people make a connection, talking about something passionate or get into a serious conversation, there needs to be a time to have a “conversational exhale.” That happens when you actually need to sit and take in what just happened and soak it in a little. Some people will sit there in silence and think to themselves. Others may just jump into another conversational topic right away. Either way, this is another way to finds out about someone’s method of thinking and it can help you better connect. In the end, if there is silence (for just a few seconds), it’s not always a bad thing.

Conversation is mostly up to the man. Yup, I said it. Yes, one of the goals is to have her talk about herself and find ways to relate to her (and she may talk more than you throughout the conversation) but in the end, as the man who approached her, you are in charge to directing the conversation and determining where it goes. It’s as simple as that. To help yourself, think about some talking points that you’d like to mention. Your initial conversation with someone who could be a potential mate can also serve as a way to find out if she holds the basic qualities of someone who you’d actually be interesting in getting to know. So if you are into travel, make sure you bring up something about traveling, whether that may be flat out asking her a direct question,

“Traveling is such a major part of my life. Do you ever get a chance to travel?”

or you can just tell a story,

“It’s funny you mention that. I went to Jamaica a couple of months ago and it was such an awesome time. I got to try out this amazing fruit fusion drink and it had all of these fruits that I’ve never had before. I love being able to go to different places, experience unique cultures and try interesting food.”

Both can serve as a “test,” to see whether she possess that same quality. Because, if you are a traveler and she doesn’t like to fly, you two may not be to fully get along.

But if you are afraid to just randomly make a statement, you can also try this. The only disclaimer is that you have to do something that most men find difficult.

Listening to what she is saying.

It’s really important for you to listen to what she is saying so that you can easily be able to relate to her with your own statement. For example, let’s say you hear a song by Eve6 playing in the bar and you say,

"I like this song. I love Eve6.”

And she says,

“Yeah, I like this song too."

You can follow up by saying,

“You know, I saw them live once at the Hatshell in Boston. You would think that a band like that wouldn’t be a good performing group but they were awesome. Have you ever been to Boston?”

She may say yes, then you two can talk about places that the both of you have seen and what you thought about it. Or she can say no and then you inquire about two things.

A. If she likes to travel

Or,

B. If she’s seen a live performance.

Either way, by following up with what she is saying (even if it may not seem as much), you can create paths of conversation and directing it where you’d like it to go.

I’m not saying that it’s easy. Takes some time, listening and practice, but after a while, conversation will definitely get easier.

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The A-Rod Syndrome of Dating

This post was inspired by a conversation I had today with Single City Guy. You should check out his blog. He’s a great guy trying to make it in the interesting world of dating.

So, you feel like you’re a quality guy. You have the confidence to walk up to most women and start conversation. You can make her smile, laugh and feel comfortable around you quite easily. You feel like you’ll definitely get her number and even a date. She seems to love everything that you’re saying. Then, out of nowhere, it happens.

 

She walks away.

It almost seems like a dream. Just a few seconds ago, you two seemed to be sharing something special together and you definitely saw that interaction going somewhere much further than what actually happened. Most guys don’t even realize what they did wrong. Others may know and not know what to do about it. In the end, it comes to one simple thing that most guys are afraid of doing.

Closing. Sealing the deal. Getting the digits. Finalizing the transaction.

Whatever you want to call it, you still never do it. You’re so engrossed in conversation (which is not necessarily a bad thing) that you are unaware that it can end at any moment. You also could be even MORE afraid of getting that “brutal” rejection when you ask to see them again. You need to be prepared to step up to the plate and take the risk. It was just as much of a risk when you approached her, so why not go all the way?

Alex Rodriguez is the perfect comparison. For years, the man has dominated Major League Baseball’s regular season, putting up ridiculous numbers. He has even been the Most Valuable Player of the American League and everything, carrying his team to the playoffs. Then, when the playoffs came around, he would go missing. He put up the worst statistics (pretty much in history) of anyone of that caliber. People gave him so much grief, saying that he couldn’t perform under that pressure; he’ll never come through and whatever else you can describe being a failure at crunch time. Until, he were to come through, that was always going to be how people would describe him.

“He’s cool, but…”

“Yeah, he’s great, but…”

“He good, but he’s not clutch.”

Then, in this year’s playoffs, A-Rod finally came through. He put up monstrous numbers as he carried the New York Yankees to their 100000th championship (this will probably be the first and last time that I mention the New York Yankees on this blog).

That’s what you need to do. You need to step up and make it happen. Stop fearing the rejection and make the move. If you don’t, you’ll actually have an even worse feeling – one of regret, not knowing what could have happened. And let me tell you something, there’s nothing that will eat away at someone’s confidence more than constant regret.

Keep pushing and be your own Mr. October.

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Live Friday RECAP

It was great talk on Friday. I was hanging out at Cafe 939 with Cort Johnson and there were tons that were discussed including the following:

 

How to really make a potential connection with bartenders and women in retail
How to initiate random encounters in places like train platforms, bus stops and walking down the street
What to do about approach anxiety
Understanding the mentality of being a quality match
and so much more!

 

See you all again next Friday as I'll be prepping for WingmanTV LIVE!

 

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Prepping for LIVE Dating Advice Tomorrow

I’m taking some time today, since my car is out of commission temporarily, to do some site maintenance and prep for tomorrow’s LIVE Dating Advice session on UStream. If you missed last week’s it ended up being a pretty good pilot.

For tomorrow, guests will be able to ask questions through the chat room. I didn’t realize until the end of the show that it was disabled. So have your questions ready. We’ll do a recap of this week’s theme, which was picking up a bartender and move over into other areas such as women in retail, sample stands at supermarkets, etc.

It’ll be fun and I can’t wait to see you all there!

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Top 3 Men's Shoes for the Fall & Winter

I was shopping with Emmi Sorokin from It's A Man's World Image Consulting and we talked about what shoes guys should be wearing this season.

For an exclusive look at what Emmi helped me get from Johnston & Murphy, check out this video.
 

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Wingman Approved

Waitress at McGreevys

Let’s get right into it. When someone in the group is interested in a bartender or waitress that is working at a bar or restaurant, I truly believe that there needs to be discussion prior to making the move. What could possibly be talked about? Well, there’s a lot that can be at risk when attempting such a move.

There’s a risk in your friend not being comfortable going back to that place. If the attempt bombs or if you two actually go out and end up hating each other, it may not be in his best interest to go back to that place. Not only will she talk to her co-workers, her co-workers will talk to the regulars that frequent the place, pretty much blacklisting him from being able to have a good time or meet people there.

Also, you friend may jeopardize the ability of everyone around him as well – including you. It’s a guilty-by-association kind of thing.

But if you trust the guy, let him do this thing and act like you don’t know what’s going on, then there’s a chance things can work out. All you have to do is give your buddy a helping hand.

So one of my buddies thought that one of the waitresses that was serving us was cute. I told him to go for it. And so he did. There was lots of energy and fun and engaging conversation, as I would only expect of him. What was important was that his friends would have the same energy and can provide the same amount of fun, which would inherently up his value to her as a potential someone to hang out with. So all I did was crack jokes, ask fun questions, talked up my buddy and be almost as cool as he was, without taking his spotlight or getting her attracted to me. Very important in the Wingman Code of Ethics. You don’t want her attention veering from your friend. You want to highlight all of the reasons why your friend is the catch and she should take chance – even if it is at a place WHERE SHE’S WORKING – to go out with him.

Then there is a certain point where you take a step back and see if he can actually get her to hang out with him outside of the bar. At that point, he’s on his own. If you are wondering, my buddy was successful and she met up with us (to be read as “him”) later on that night.

The point is this: if you’re out with friends at a bar or restaurant and one of them really wants to try to get a date with the waitress or bartender, have “the talk” first then be fully supportive in helping him get there. It’s a rare feat but one that’s totally possible.

Keyword: SUPPORT

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“Be My Fitness Wingman” Facebook Contest

Here’s a fun contest that I’ve wanted to do for SO long. As you know, fitness is something that is very important to me. It’s also a great way to boost confidence. Having a healthy body means having a healthy mind. But, in a world filled with excuses, we always try to convince ourselves why we can’t workout or get a membership at a gym.

“The gym is too far from my house.”

“I can’t workout at home.”

“I’m too busy to workout or go to a gym.”

“A gym membership is too expensive.”

As someone who has been guilty of these excuses in the past, I understand where you’re coming from. What I have realized is that you make a choice. You either do it, or you don’t. Working out and exercising is either a priority or it isn’t. And it will show. You may not have as much energy throughout the day. As a guy, your testosterone level will decrease and so will libido. You may get a little plusher in places you don’t admire. You don’t feel as confident or sexy as you used to. These should be the excuses you make to GO to the gym or to exercise.

I’ll be brief with my motivational speech and just announce that every month, I’ll be giving away a one-month membership to Revolution Fitness. This contest will be for Boston locals only (sorry, but don’t worry, I’ll have another contest for everyone else later this week!).

So, what is it that you have to do? 

One thousand pushups. In one try.

No, actually all you have to do is be a Facebook Fan. That’s it. So if you’re not a Fan of the Wingman, go join now and you’ll automatically be entered to win. A winner will be chosen at random at the end of the month and if he or she is a local, he or she wins! It’s that simple. 

So go join the Fan Page and give me a shout out! 

If you don’t know about Revolution Fitness, here’s a brief description of why I love to workout there. 

Revolution Fitness is located in the South End of Boston. It IS your neighborhood gym. But not only is this gym filled with incredible trainers, instructors, and a friendly fitness staff, there's a ton training equipment that will make your workout unique every time. Programs vary such as CrossFit, RevFit’s unique Dynamic Fusion and their new Helix group class. Inventive training and one-of-a-kind classes are mixed with state-of-the-art workout machines. Members can find everything for a fun, effective workout in a friendly, energetic, and professional setting. This place is the real deal. 

And as a bonus, since I am all over Boston, I will hand out one FREE day pass to the gym every day. All you have to do is come up to and say, “Be my fitness wingman.” This day pass will give you full access to everything in the gym, including classes that they offer. 

Not bad, huh? Well, let’s get started!

Join the Wingman Fan Page!

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I’m in NYC!

No I haven’t moved…yet. But I am out here on some serious business and some pleasure – never bad to mix the two when you can, right? If you’re in NYC and want to meet up, let me know! In the meantime, expect a little bit of silence on the blog over the next few days.

If you need to feed your hunger though, watch this week’s WingmanTV.

But then, expect some amazing news when I return. 2009 is almost done but I still have a few tricks up my sleeve…

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Wingman Approved

Dating 101: The Simple Guide to Attraction

 

This winter, I will be teaching a class at the Boston Center for Adult Education. I am REALLY excited to be doing this, as it’ll give me a great opportunity to help more people at the same time in a more efficient manner. Each class is designed to never be overwhelming and give you information, tips, guideline and advice that you can use the moment you walk right out of the door.

Here is the course description:

“Delve into what keeps you back from having successful interactions with people you are attracted to and find the solutions to those issues, while understanding the process of meeting and attracting someone. Topics to be covered include, approach anxiety (why you have it, where it comes from and how to handle it), being a good conversationalist (how to avoid “the interview” and still get the answers you are looking for), body language, flirting, identifying signs that someone is interested, image presentation and timing risks (when to ask for the number, date, etc.). There will be in-class demonstrations so everyone can get a clearer idea of what to look for and an open Q&A to answer any questions. 

People who have been having a hard time getting dates, creating attraction or just flat out approaching attractive people will be able to use the material learned in this class the moment they walk out.”

There are five classes running every Saturday (11AM to 12:30PM) from November 14th through December 19 (No class the weekend of Thanksgiving). And no, there will not be a final exam, but this course is designed to push you through your comfort zone, make you feel good and have you enjoy yourself while learning a wealth of things about you that makes you attractive.

Tuition for non-members is $120 and $96 for members.

To register for the class, get more information and look for directions, check out all of the details at the Boston Center for Adult Education site.

Even if you’re not interested, put this in front of someone that may be. At $120 for a 5-class course, this is a REALLY amazing deal and I am NOT going to do this for too long.

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Do You Want to Enhance Your Dating Life?

If so, sign up for the Wingman newsletter for free dating tips and exclusive content! Also receive my free eBook, The Other Twenty Percent - The Starter Guide for Instant Dating Success. One of the easiest and effective ways to see dating improvement.