Ask Out EVERY Hot Girl

This video comes from the inspiration of Gary Vaynerchuk and a comment he made during one of his keynotes. It's stuck in my mind and I want it to stick in yours as well.

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Wingman Approved or Unapproved? You Decide.

Buying a Woman Drinks

 

Clients ask me this all the time and I am going to put it to rest NOW. When it comes to buying a woman a drink, NEVER BUY A WOMAN A DRINK.

I know women out there are upset and that’s ok. I don’t care. There are reasons why I say this. It’s all about context. And here’s why.

Wingman Unapproved

Don’t buy a girl a drink within five seconds after meeting her. While no woman will REALLY refuse a free drink (in fact, women spend little amounts at bars for this reason alone), the moment you offer her one, it’ll only mean one thing. Even if this is not what you are trying to say, you are still saying this,

“You are hot. I know nothing about you, but I am willing to buy you a drink in hopes that I can validate myself to you. Also, you’ll be a little more liquored up and so maybe more likely to let a guy like me talk to you.”

It’s pathetic. You buy the drink, she takes it and then stands there, hoping that you’ll just walk away. She’s not really going to walk away until the drink is finished because she feels bad and it’s rude so she’s willing to give you at least the time it takes her to finish the drink. Yeah, you can win her over in that time, I suppose, but you’ve already put the odds against you from the start.

Also, don’t offer the girl you like a drink and not her friends. That is just not cool. If you ever want to be cockblocked, pull this move and it’ll be 100% effective. Why would you NOT offer her friends a drink? Is she THAT special that only SHE deserves the benefit of getting a drink from you out of the entire group? Want to know what you say then?

“I’m a douchebag.”

Either of these moves will be a #fail.

 

Wingman Approved

If you must buy her a drink, if she’s with a group, you are buying everyone a round. Personally, if you have the ulterior motive of trying to get with the girl, it’s not worth the investment of buying everyone a drink. BUT, if what you are trying to say is,

“You guys are cool, let me buy a round for you guys,”

and you actually mean it, then it’ll look SO much better.

Another situation of buying a girl a drink would be if you two were alone, whether isolated from friends or going over to another bar that night. Obviously, it’s been insinuated that the two of you would like to get to know each other in more of an intimate environment. If you are going to buy yourself a drink, it makes sense then to buy her one as well. It’s a good gesture and because you two have already gotten to know each other a little bit, the thought expressed above will less likely run through her head. Why? Because now you are having conversation over a drink as opposed to drinking over a conversation.

 

Pretty simple guys. Save your money or spend it on yourself.

*Wingman Approved/Unapproved is for entertainment purposes only. This is NOT advice and is only produced to evoke fun discussion and conversation. Misinterpretation of this as advice and using it in a social environment may result in brutal rejection, a drink thrown at you, a punch in the face and/or a huge social value drop. The Professional Wingman is not responsible for such misinterpretation.

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Women, Why Won't You Approach Guys?

I came across this post a couple of days ago and I had to re-post it on my blog because it's so funny to think that after millions of years of socia interaction between a man and woman, things still stay the same - EVEN THOUGH it's has been proven time and time again that doings things differently can produce better results. What am I talking about here?

Women approaching guys. This post is from Single City Guy. Check out his blog.

The question of approaching a potential date has come up in a series of recent e-mail’s and conversations with friends. On Twitter I asked if women approach guys or do they prefer to be approached. Between the responses I received and the answers from my friends the answer is fairly unanimous, women prefer to be approached leaving the sole responsibility on the shoulders of us men. You would think after some several million years of evolution of hunting and finding what we want, the hetero-male-sapien (if that’s not a word, it is now), would have patented this process. We haven’t.

Men face a lot of doubt when approaching a woman, regardless of our level of toolamship. There’s a reason Mystery’s three second rule works really well. It gets us to stop thinking and just do. The more confident and sure a guy is, the more comfortable they are in approaching a woman. The other strategy is to let things “naturally” progress, gaging our approach through more social avenues. Regardless of the type of guy and his method of approaching, we love it when a woman approaches us.

In an honest conversation with a friend, I told her “The same way you MUST have that pair of shoes is the same way you must think of dating.” Stop window shopping your only going to drive yourself crazy. Grab what you want, walk up to the counter and pay for it. Like any purchase it may fit you for years or you may end up asking for a refund next week. If you like a guy, try talking to him and ask him out, making it known that you are interested in him.

Approaching a guy doesn’t make you a slut or overbearing. When we’re approached it signals that this woman is interested. If your afraid of coming on to strong or making him think you just want sex, you’re probably approaching the wrong guy. We do not think any different of you if you approach us or if you don’t. A guy who just wants to add you as another notch to his bedpost will think of you the same way regardless of you approaching him or he approaching you.

How should you approach a guy? Easy, ask him out for lunch, drinks, coffee. Get creative if you have to, women your a lot better at getting our attention than we are!

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The Wingman Labs: Wingwoman?

People have asked me if it’s better to have a wingman or wingwoman in these kinds of situations. My answer: it depends. Think of it this way.

For those that watch Entourage, you’ll get this REALLY quickly.

Example wingman: Vincent Chase

 

The man is a superstar and can pretty much get any woman. The fact that I can just walk with him makes me look like a superstar as well. Why? Because the fact that Vinny wants to hang with me tells people that I must be a cool guy to have Vinny want to hang with me. This is how Turtle and Eric have been able to work their ways up to live the lives they’re living now.

The similarity here is that if you're hanging with your best friend(s), they are going to make you feel as though you have it going on, which will be a natural confidence boost. Women like guys who are comfortable in their own skin and can have a good time. A quality wingman will make you feel like the man all the time.

Example wingwoman: Brittany (Eric’s Assistant – played by Kate Mara)

An awesome friend and she’s very beautiful. Definitely can do everything that a typical wingman would do but she serves as standing proof that hot women like to be around you. That is the only thing having wingman can’t do for you (unless he can make up in other ways, such as wealth, fame, athletic stature, etc.). Women see this and they can actually feel better about the fact that women are comfortable around you. There’s also the wonder of if the two of you are dating, which inherently creates a jealousy complex that can drive women nuts and make you appear that much more appealing. That within itself is the true value of having a wingwoman.

I think I might be running the wrong service here.

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The Wingman Labs: A Set of Commandments of the Wingman

When you are going out with your boys, you’re out to have a good time. Every so often, you will have a chance to get to know a group of ladies and one might catch your eye. It’s important that if there is a chance for success that you and your friends are always on the same page. A wingman has bigger responsibilities than one would think. You really could create an entire system. Like how I did.

But anyone can be a quality wingman if they just tried. So, here is my basic foolproof system of being a good wingman to ensure your buddy success at the end of the night.

THOU SHALL BE WILLING TO SACRIFICE YOUR SUCCESS FOR HIS.

If you can’t let one night go by without being on the hunt and instead help your friend, then you have NO shot at being a good wingman. You will have your day. I promise. Don’t make the night about you. It’s selfish and it won’t help your buddy. No need to be jealous of his success either. Help him out. If you notice that people are paying more attention to you and not him, do whatever it takes to defer that attention to your buddy.

If the girl your buddy is hitting on has friends, you must go in there and entertain them so your buddy can focus on the girl. Most guys know this as taking one for the team. This is also a good time to talk your buddy up with her friends to assure them that he’s a good guy.

Whatever is the best thing you could say about your friend, make sure you say it. You’re the only person who can really validate him so if you’re serious about how good of a guy he is, no one will question your authority.

Tell stories about your friend that talks about how cool, fun, smart, wild, and/or funny he is. You can totally make fun of him but in a way that makes him a good guy. Tell them how you make fun of him because you caught him making baby noises to his nephew.

Probably the most important quality of a wingman is their lack of shame. I have a bunch of friends that just don’t have any when it comes to helping another out. It’s a no fear kind of thing. If you know that your friend has a legitimate shot at success, don’t be afraid of the potential for humiliation if it’s going to seal the deal for your buddy.

THOU SHALL HAVE A SIGNAL SYSTEM SET UP.

 

The other night, I saw my friend talking to two women and I was trying to figure out if he wanted me to come help him out. He had no idea what I was trying to signal and so he left and walked over. Come to find out, he actually did want my help but then lost the women.

There needs to be something, either hand signals, eye contact or whatever, so that your buddy knows what your situation is.

THOU SHALL ALWAYS LOOK LIKE YOU’RE HAVING A GOOD TIME.

No matter what the circumstance, you must bring the E & O! No one wants to be with a Davey Downer and women can smell pessimism like a terrible odor. It reeks.

Tomorrow, I will address the huge debate of whether or not it’s a better idea to have a wingwoman over a wingman.

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Wingman Approved or Unapproved? You Decide

Cockblock/Catblock


This has been a huge topic that many people have been emailing me about. If there is any time that I would want conversation to happen, it has to be with this.

The idea of cockblocking and catblocking.

Yes, as men, I’m sure we’ve all been victims of this. I imagine this kind of thing can only happen at a bar, nightclub, or private house party. The night is going well and you are having a blast with this girl who seems to like you for some unknown reason. You two are dancing and getting it on, on the dance floor. You two kiss a couple times and it feels awesome. You can see the light at the end of the tunnel. You ask, she agrees to go back to your place “to see your Kurt Cobain Anthology” and is ready to leave. But before she does leave, she wants to let her friends know that she’s bouncing early.

After following her for what seems like forever while she’s looking for her friends, she finally finds them and tells them the deal. You think it’s in the bag and all of a sudden, her friends, without hesitation, grab her from your hand and pull her into the darkness and you never see her again. As she fades into the background, you hear her screaming, “But I like him. He’s cute” only to hear the response of, “You’re drunk. You just met him. You’re coming home with us.” You’re left there with empty hands wondering what just happened. You leave dejected and unless the good graces from heaven drop a woman on your head – literally – you may have to go home alone that night.

You've been cockblocked.

Now on the flipside, I have seen guys catblock (I’m hoping to have made that up) women. Although VERY rare, I guess these women are notorious for ruining men’s lives after having relations with them (i.e. bad rep for having reckless sexual activity with everyone, being a stalker, etc.) and maybe one of these guys that’s initiating the cat-block is aware or has been a victim of this woman’s destruction. For what I have seen, it seems to work just by one guy telling the other not to do it, while giving reason, of course. Usually, a guy will trust his boy and adhere to the sound advice.

Here’s my gripe with this. What’s the deal with all of the blocking? On one hand, it could be Wingman Approved because you could be saving your friend from impending doom. Then again, it could be Wingman Unapproved because you are stopping a friend’s chances of having an amazing time for that night. I stress the point of just that night because for right now, that’s all it is, until there is an indication of the possibility of more than just one night.

For this, I can only speak from the male perspective of countless people emailing about what to do when they come across this situation. Here is a female’s perspective on the topic.

I totally understand that we are to look after our friends. I do it all the time and I think when others do it, it’s admirable. But listen, we are adults. If we want to go home with someone for the night, why can’t we? What makes it so bad? If the guy is wasted and trying to drive her home, cock-block. If the guy looks like Ron Jeremy, by all means cock-block. But would you cock-block me from your friend if she really wants to spend the night with me, I’ve spent time getting to know all of you and have given no indication of being a creepster? I don’t like having to put myself in here but as a victim once in the past, I’d be curious to hear thoughts on that.

Some guys (and some women) believe that the other women tend to get jealous because they can’t find a guy to be with that night and so the rule, “if one can’t, no one can,” comes into effect. Is that true? I mean, I know that if my buddy was able to meet someone that night, I’d be cheering him on, regardless if I didn’t meet anyone that night. Why don’t I ever see women doing the same? It’s just an interesting thing that has confused many of us for years.

I’m sure many of my readers here are looking for growth within this issue more than a solution. So let’s keep it clean and fun.

Thoughts? Comments? Concerns?

*Wingman Approved/Unapproved is for entertainment purposes only. This is NOT advice and is only produced to evoke fun discussion and conversation. Misinterpretation of this as advice and using it in a social environment may result in brutal rejection, a drink thrown at you, a punch in the face and/or a huge social value drop. The Professional Wingman is not responsible for such misinterpretation.

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What I Really Learned While on Vacation

It was my first trip back to Jamaica in 6 years. My family is from there and although I could have stayed with family, I decided to stay at an all-inclusive resort. Considering that I was staying with my older sister, brother-in-law, nephew and my mother, there wasn’t anyone that I could REALLY hang and party with while I was there. So I was on my own, which meant one thing. I had to create my own fun. Part of that was making new friends.

Here is one thing that you should think about wherever you are – especially when you’re on vacation. If you see someone you’d like to talk to, go and approach them. Chances are, you’ll never see them again, they are NOT going to blow you off (pending you’re not creepy), and if you do get rejected and there is any shame, you can leave it at the vacation spot. YOU HAVE ABSOLUTELY NOTHING TO LOSE.

When I went to the bar, I began talking with the bartenders, who were relatively young (around my age), and our conversation sparked conversation with other people at the bar. By the end of the first night out, I had made about 4 or 5 friends that I could hang out with while on vacation.

When it came to women, I feel when you’re on vacation, you should feel as though there is more room for mistakes because under the pretense of having nothing to lose, you can afford to make a couple errors. I’ll tell you what. The same thing applies when you’re back home. If a woman makes direct eye contact with you, she is telling you it’s ok to approach her. One night, a woman and I were exchanging eye contact throughout the night. I was having a good time with friends so I was in no rush force things. When I finally approached her, we ended up having a great time and spent a lot of our vacation together. There were other women who I talked to and made connections with but it all happened because I took action on a present opportunity. You need to do the same too, no matter where you are.

It’s not about being cool or letting her know how awesome you are. It’s about having fun and not caring about what could happen. You only have the ability to work with what IS happening at the moment and what you can MAKE happen.

Learn to spread your energy and your value wherever you are. People find that kind of personality infectious and they will gravitate toward you. I remember (for the most part – I had A LOT of alcohol while on vacation) every night I was talking with a different group of people. Some were my age, others were married couples that’ve been married forever, some had just got married, and so forth. I was listening to their stories and I was sharing mine. By the end of the night, people were dying to hang out with me again. And by the end of my vacation, everyone knew who I was at the bar. Bartenders knew me by first name and we taking care of me first (which helped my mother and brother-in-law get served a little quicker whenever they needed a drink). Some people threw a farewell get together for me on my last night. I even had people who were in the lobby looking for me when it was time for me to checkout and leave. It was one of the best true vacations that I have ever been on.

Since I’ve been back, there has been a drive stronger than anything I’ve had since I’ve started this blog and this company. My relaxation is at an optimal level. My sister said it best. “Dude, if you were any more relaxed, you’d be dead.” The vacation was a deal-changer in the sense that it’s changed my perspective on time, value, energy and everything else that’s important to me. The game has changed and that game is my life.

I am not boasting for the hell of it. These people were awesome and I plan on keeping in touch with as many of them as possible. I had an amazing time and these are the types of things that I have always taught my clients and blogged about incessantly. I hope you guys can take these tips and my experiences and make them your own. Whether you are in your hometown and know a lot of people or on vacation and know absolutely no one, you can make your experience an amazing one if you just let go, take some risks and live in the NOW instead of the future of POSSIBILTY and FEAR.

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Two-Column Theory to Approaching Women

As I was sitting on the bus headed back to Boston after an amazing weekend, I figured I’d take the time to look back at some interesting points that were made over the weekend. After shooting a WingmanTV episode that I did in NYC, my guest and I were talking more about dating and meeting women. He brought up something interesting that I’d like to talk about.

He said that when it comes to approaching women, as an older guy and knowing what he wants, he’ll look at a girl and place her in one of two columns.

Column One – “You look like a fun time.” He carefully looks at her and decides if she can be someone he can have fun with. You have the kind of fun that can be just for that night. You also have the fun that can bring lots of energy and conversation for an extended period of time. Finally, you have the kind of fun that you’d want to be with for a VERY long time – potentially, the rest of your life. In this, he also included attributes such as low-maintenance, non-elitist attitude and friends. Yes, he does this just by checking her body language and how she’s carrying herself in the crowd.

Column Two – “You look like you require too much.” This column has women who look and act as though they are very high-maintenance. The kind of girl that would make you buy her a drink before talking to her or else she won’t give you the light of day. In the same column are women who are less mature and don’t carry themselves well in a social environment (they get wasted and make a fool of themselves). Once again, he will just look at body language, how she behaves with her friends and other subtle things.

This idea really intrigued me. It was almost like in the Terminator when he did a scan of people and their entire profile would come up and at the end, determine if they were dangerous or not. So I decided to adopt this for the day, just for fun, to see if you really can simplify things to the extent that allows you to determine if a woman is WORTH approaching.

That idea changes things a little bit because we’re not talking about the ability to approach attractive women. This goes beyond it in the sense that even though a woman can be a smokeshow, she still may not be worth you going up to her if there is a good chance she’s not going to rock your world.

So anyway, it started with walking down the street and looking at women and deciding if I would want to talk to them. This felt a little weird because it seemed as though I was harshly categorizing women and not really giving them a fair chance. I acknowledge this is something that should be frowned upon but I also see people do this everyday without remorse, especially when it comes to selecting a potential mate.

The problem that I see with this is that it’s not a perfect system. There will be times where you will put women in the wrong column. For example, a REALLY attractive woman who spent over an hour getting ready just so she can look incredible and may not get approached by any men, could have the “look” of a high-maintenance woman. The problem with that is her looks could be so intimidating that men are afraid to approach her, which makes her look untouchable when in fact, she would have LOVED for a guy to approach her.

If you remember my Wingman Unapproved post, you saw that the women we ended up talking to were happy that we talked with them because no one else had the “testicular fortitude” to do so. And they made a point to say that they are VERY friendly and would be open to talking to any guy just as long as they’re not creepy. But I digress…

In the end, this system can prove to be efficient for the kind of guy who is most likely older, is more sure of what he wants and has enough dating experience to be able to anticipate what he is getting himself into. I wonder how many of those guys exist?  It should be known that even with this mindset, there is still room for error with that theory. For someone who is younger and still searching for what he wants in a woman (and in life, in general), this may not be the best system. At all. But a fun one to joke around with.

Still interesting either way.

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Where Would You Like Me to Go?

I have been reviewing many places in Boston and I’m having a great time creating these reviews for you guys. As I review more places, I’d like to be sure that I am reviewing places that people are curious about. So, this is YOUR chance to find out about other places I haven’t reviewed yet.

Let me know what places you’d like to see reviewed. As long as it’s in the Boston-area (I’ll include Cambridge), I’ll go out there and review it. As small as Boston is, there’s no way that I could have been to EVERY place there is. So let me know of some places, and I’ll have some reviews for you!

You can leave places in the comments, or you can send me a tweet with the place you want me to check out.

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