Tough Love #4: Daddy and Dating

This continues my posts of Tough Love, a series of posts, giving direct advice to women based on the weekly VH1 show, Tough Love. If you have missed out on other posts, feel free to check out the other ones.



Week 1: Creating a First Impression

Week 2: Communication

Week 3: Being Sexy

Week 4: Daddy & Dating

This should NOT be a revelation for many women. A woman’s relationship with their father is a huge reflection on their relationships (or lack thereof) with the guys in their life.

Many doctors have said this and it doesn’t hurt to keep talking about it because many women may not know how to break through this major hurdle in their dating lives.

A woman’s relationship with her father tells just as much as a man’s relationship with his mother. I was never REALLY aware of this until later on in life and even then, I was very ignorant of it.

With many girlfriends who didn’t have great relationships with their fathers, I always let it slide, thinking that it was something else that I just didn’t understand.

Little did I realize that there was a strong connection between the two.

To make a giant leap towards getting through such a difficult sticking point, you have to reconcile with your father about the relationship (or lack thereof) and how it has affected your LIFE, let alone your dating life.

This reconciliation can range from writing your emotions down and reading them to a peer group to actually confronting him and saying these things to him (granted, he’s still alive or around).

These kinds of things can affect someone’s entire life without them even knowing, just from the decisions they make, how they react to situations and how they manage relationships both intimate and platonic.

When I was growing up, I had shitty relationships with my older siblings and it affected me when I was in school. I got picked on all the time and had NO idea how to even go about sticking up for myself.

Then when I got into my first fight in elementary school, I put someone in sling for a couple weeks, I realized something was wrong, but never knew what to do about it so I bottled up whatever it was inside. Before my older sister left for college, she left a letter for me apologizing for the way she treated me and actually loved having me as a little brother.

That made me feel amazing and I knew that my sister wanted to be involved in my life. Fortunately, my relationships with my older siblings have dramatically improved since I started high school and have been awesome since.

I have been able to learn a lot from my experiences, both past and present and use what I have learned to HELP my relationships grow and not sabotage them anymore. For that, I am grateful.


As an aside, there was also a point of making sure that you and the guy you are with are on the same page. You have to make sure that the guy you are with aligns with what you want and what you are looking for (in a future sense).

DO NOT let a cute face distort what you hear. If you are looking to settle down and he’s looking to find someone to party with, you have to be able to know the difference and understand that it’s not good for what you want.

Sure, he’s good looking and he’s saying and doing all of the right things, but that’s only good for RIGHT NOW. He won’t be good for LATER and in turn leave you back at Square One, frustrated and with a higher sense of insecurity that will certainly go into the next relationship you start or at the very least show with the next guy you meet.

Keep your ears free from filters and understand the difference between what you are hearing and what you are actually seeing.

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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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.

My Cousin's Wedding - A Growing Up Series Part 2 of 2

This is continuation of the growing up series I started last week. There was a lot of information there that I wanted people to take in and since then, I have been able to relax, re-focus on what I need to do and come back stronger than ever. Here are some more of my thoughts, let me know what you think.

In perspective, we will truly never know whom we’ll end up with. He or she can be someone from the present, the past or the future. But we won’t really understand that until we have a chance to look back. Clearly, this kind of thinking may not be beneficial for some. But for the way I think, it’s important that I remind myself of that so that I don’t get stuck in the past and can make the best of my present for the best future possible. Sometimes, we get caught up thinking something HAS to be when it doesn’t have to be at all. Like I’ve said before, life doesn’t care about your plan.

Family will always be a big part of my life.
No matter where I am and what I am doing in my life, I will do my best to keep my family around. They had the responsibility of bringing me up – a task that I must say was a hard one – and they all have always been my biggest fans. Seeing my aunt so happy to see her son get married is something I can’t wait to share with my own parents. They have done so much and continue to do so to see that I become the man I want to be and for that, I am eternally grateful.

There is a time and place for everything. For the people who feel hopeless when it comes to dating or may have had their heart broken at some point in their life, once again, it’s important to keep things in perspective. Time will NOT let you go. Like I say, sometimes, things cannot work out because of timing. Sometimes, you may not be ready and don’t even realize it. Other times, there are other circumstances that will just not make a relationship progress. Whatever it is, you have to continue to do your best and not to be hard on yourself. I told one of my clients the other day that as much as your past experiences have brought you to where you are today, it’s important that you give the next person that comes around a fair chance. If you don’t, you may be setting yourself up for self-sabotage, which I personally think is one of the major reasons why most people are single today.

One of the most powerful things in this world is forgiveness. Forgive yourself. Forgive others. We only get one shot at life. There isn’t a practice round and there’s no run-through. We are ALL going to make mistakes. And like social media, business and anything else in life, it’s all about how you respond. What have you learned? How are you going to bounce back? What’s your first step forward on your road to recovery? Have some pride in who you are and be determined to live the life that you truly believe you deserve.

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