What Women Can Learn From Tough Love

Some of you can’t stand reality TV shows. Others love reveling in someone else’s drama and demise. Personally, I have a love-hate relationship with reality TV. I remember a few summers ago, I was addicted to VH1’s The Pick Up Artist, Scott Baio is 45 and Single and Rock of Love Season 1. There was something about these shows that drew me to make sure I was home to watch them every Sunday night. A year later, it finally occurred to me what that was.

I was addicted to analyzing the progress of people’s personal development.

I figured that by watching these people through the various personalities and tribulations that they went through, I could find something that I can learn to help my life and know what to do should I encounter a similar situation.

Unfortunately, those shows are purely for entertainment and have zero educational quality these days. However, there is one that has a little bit of educational value.

VH1’s Tough Love.

Over the course of several weeks, I’ll have a post talking about the theme and what you can learn from each episode. I am a little behind schedule here so stay tuned later today for a quick updates from the first three episodes.

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Meet the Parents


I remember growing up and watching TV how bringing a girl home was a big deal. It was especially so during holidays such as Thanksgiving and Christmas. Actually, no, it wasn’t a big deal.

It was a HUGE deal.

This woman had to be someone that I was strongly committed to (dare I say, the one?) and wanted to not only show her to my family for their approval, but also to share a very important part of my life with her. You really don’t reach that level of a relationship until you two meet the parents. That’s what I was led to believe.

After bringing very few women (can definitely count on one hand…with a few amputated fingers) home to meet my parents over the course of a decade, I’ve realized a few things that have changed my perspective on meeting the family.

What’s the big deal? It’s your parents. No offense but it’s not like you’re a part of the First Family. Sure, this person you are bringing home is more than your friend, but you know what? If your parents are cool, they are going to treat them just the same and it won’t mean anything different. So what’s the big deal? Yes, I understand that it varies across many cultures but I am only speaking from the one I’ve been a part of where dating can be perceived these days not only as a sport, but also a disposable product.

The true difference in when you actually meet the parents is relative. If I am in a relationship for one month or for nine, it’s not going to change the effect that my family meeting my significant other will have on my relationship. If my parents hate her, well, it just means that we may have some rocky ground ahead. My parents’ support of whom I am with is important to me. Period. On the flipside, if my significant other can’t stand my loud, crazy and fun uncle and he’s my favorite uncle, the outlook of the relationship will not be good since as long as I’m with my family, my uncle will be there.

The actual meeting of the family is relative. Sure, I’d love for my girl to love my family and vice-versa. But even still, it has played no true effect on whether or not I wanted to stay with her. My family will always be there and so will my girl, if she so decides. And if feelings are strong enough, there will be a possibility of a co-existence despite the disagreement. Yes, that statement is more of an E & O belief, but one that I have employed and has worked in previous relationships (and let me be clear here: the breakdown of my previous relationships had everything to do with the actual relationship and nothing with my family and their getting along with her).

So am I telling you that it’s better to get it out of the way sooner than later? No, not really. Am I telling you to disobey your family values and beliefs? Absolutely not, not unless they don’t coincide with yours. What I’m really saying is meeting the family is not that big of a deal and as someone who values his family more than anything in life, I have NO problem in sharing what I value most with anyone else. It’s just a more intimate situation because your significant other inherently feels a state of heightened emotional connection.

I am a huge fan of this state.

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What's on Tap for The Professional Wingman

Hope everyone is having a good week so far! Here's what in store for this week and what's ahead as we push toward 2010!

Off the grid for Thanksgiving. As you know, family is number one to me. I'll be going to Maryland to visit my newly born niece and other family members. So content and services will be shut down after tomorrow and through Sunday. Expect an interesting post about dating and family tomorrow to close off the week.

WingmanTV. This past week's WingmanTV is the best episode I've done so far. Meet Cort Johnson. He's one of the men behind DARTBoston and the co-author of the line, "it's all about E & O." Listen to an in-depth conversation that Cort, Brenda (bartender from Vox) and I have about the origin of E & O and how it can be applied to many aspects of your live, including dating. You can see the show here.

And don't miss the next WingmanTV at the Lansdowne with special guest, Tom O'Keefe, better known as @BostonTweet! Details and RSVP information will be out soon!

Bar and Date Spot reviews done through mobile. So I was able to sync my Squarespace with my iPhone and now am able to post on the fly. What better way to do it is when I'm out at these cool places. So, any ideas and reviews I can make on cool date spots and bars in Boston, I'll put them up (with live pics as well, of course). That should be fun and more helpful for you guys.

New venture coming soon. On December 1st, you are going to see a subtle shift in how the Professional Wingman is going to operate and also see a new site! All will be revealed then but stay tuned as you get to see the continuous evolution of the Professional Wingman!

As always, keep it simple and enjoy the Thanksgiving holiday!

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Review of Beacon Hill Pub

Address: 49 Charles St

Who Goes There: young neighborhood people, ages 23-30

Price: $

Best Nights to Go: TBA

Specials: drink specials to the max, including $5 drafts

Beacon Hill Pub is a great place for young people to show up. If you're here with friends, there are plenty to things to entertain you including basketball!

Mostly guys usually come because it's your typical dive and there's cheap beer but there's a decent amount of women that are here now. I can imagine more would come on busier nights.

The place is split into to "sections." Both are the same, except one room has the ball game.

Staff is friendly but it's not the best place I'd say to meet women or have a good time with friends. Not that it's terrible but there are better.

And, it's @JustinObey's birthday so be sure to give him love.

Rating: 76 C

Show Your Cards From the Get-Go

Not four months in.

This is a piggyback post from Kelli Lawless and her blog, Dating and Mating in America. When I read the headline, I was very curious. Then after reading it, I got upset. I got angry. It pumped me up so much that I can’t fall asleep on the BoltBus anymore. I might as well talk about this.

Too many guys do it.

You see a woman that you like and you want to be everything to her. You want to be everything that she likes and wants in her ideal man. You want to be the man she wants to marry and be with forever. But did you ever ask yourself,

“ARE you that man or are you POSING?”

This is a serious question to ask. There are too many men that ask me about what lines they should use on a certain type of woman and how they should dress to get with another type of woman. Fortunately, I don’t give them this kind of advice but they can definitely get it elsewhere. And men read and practice it to a tee. But beyond all of that, would you like to know what’s even worse?

It actually works.

Guys dress and act like the men women are looking for and women eat it right up (can you blame them?). Then, after a few dates or even a few months, they feel as though “they have them.” Now, they can “let up” and start being themselves.

As I type this, I feel like what I am writing doesn’t even make any sense.

Then, women are left wondering, “WTF?” and run for high water, leaving men thinking that they screwed up some other way.

Lather. Rinse. Repeat.

Listen, you are the problem. You fucked up from the get-go. You weren’t yourself. It happened to me when I was in college. I made so much effort in being the man everyone wanted me to be, and less effort on making who I was even better. Then, when I figured I had it all, I reverted back to what I was used to. I mean, think about it. Being someone you’re not is A LOT of work. Now that I have it all, there was nothing better than going back to being me. After that moment, I started to lose everything to the point where I had to start over from square one.

Now, after doing it right and sticking to being myself, I find there is even MORE value in being YOU rather than represent this figurative ideal. To people who will still alter who they are to appease to someone else: Fuck that. If you want to be someone else, go apply to be someone’s body double for a movie. Stay true to who you are, and I promise you will persevere. Being you is enough work to give yourself but it’s the easiest because that’s the only thing you know how to do best.

Remember the goal: to get someone to love you for YOU, not who you’re not.

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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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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.