Ask Your Wingman – A New Chapter Beings

As the summer is winding down (unfortunately) and people are already thinking about school (disgusting), I think now is a good time to assess yourself at the year’s midpoint. Think about where you are in your progress in accomplishing the goals you set earlier in the year. Are you on your way to reaching them? Did you get sidetracked? Do you even want to accomplish those goals anymore because your priorities have changed?

Then think about the rest of the year and what goals would you like to accomplish. Are they reachable? I remember my senior year in college, I had SO many goals that I wanted to reach besides just making sure I graduated. As an RA, I wanted to use that authority to not only build relationships with the staff and kids on my floor but also to make sure that my floor was the party floor in my building – party in the sense that we get all the girls to come and hang out with us all the time. So I set up a plan to make sure that was possible. In a matter of only couple of weeks, my door and a few others were constantly being knocked on by the hotties in our building, which one of them ended up becoming my girlfriend that year.

As fun and silly as that plan was, whatever you decide to do, make sure you have an action plan and that you go balls to the wall with it. This might be college-focused but you can use this for any stage in your life. It is YOUR responsibility to control the outcome. Never give up. Never back down.

Mailbag time.

I met a girl online and I’m planning on asking her out to have a few drinks to get to know her better. I live in the ‘burbs so I’ll be going to see her in the city. Should I get her to pick a place since she’s more familiar with the area or should I just pick a place that I might like and take her there?

What I would do is make the effort to find a place. It’s a thoughtful gesture that she’ll appreciate. And it shows that you take action fearlessly regardless of the situation, which is an attractive quality. Pretty simple there.

How can I control my defenses to not take things so personally? I’d like to think that I am pretty secure with myself but based on what other people have told me, apparently I’m not. Even if people are joking, I seem to feel a little attacked. I get confused as to what I should defend and what I should let pass. Maybe the people that I am around aren’t that great of people but I’m not sure. What are your thoughts?

This is tough because the information you’re giving me is a little vague. But I’ll do my best here. If you are taking things too personally and you know that people are kidding, then you need to man up and brush it off. If they are kidding and it still offends you, be mature and politely (and sternly) ask them to tone it down a little. Nothing wrong with that. If they don’t respect your request then you need to look for new friends. Otherwise, if there is no harm, you should have a sequacious attitude toward it and move on.

I don’t know how old you are but you should be able to visibly tell if someone is out to hurt you or to just make light of a situation (sometimes at your expense). A sign of self-security is someone who is okay to make fun of themselves and acknowledge his or own quirks. No one’s perfect, therefore no one should be capable of bringing you down. Only you can. It’s your responsibility to control your own emotions and not let others control them for you. Always remember that.

I have a yearlong friend who I will be taking out. We’ve never been romantic but I’ve recently been growing feelings more than just friendship. She said yes but I’m not sure how nice of a place I should take her and if she even knows if it’s a legit date or not. How do I know?

As I always tell my clients, in order for it to be a date, you have to state the intent of it being a date. If she doesn’t know it’s a date, IT’S NOT A DATE. Sure, if you go all out and impress her, she may get the idea but would you want her to get the idea DURING the date or BEFORE the date? BEFORE the date gives you a better chance because if she knows and agrees anyway, then you know she may be interested. If it happens DURING the date and she didn’t know, it’s really a 50-50 shot. Personally, I think you have less of a chance because chances are she’ll be overwhelmed and not know what to make of the situation – especially if she didn’t even think about you in a romantic way prior to her realization.

How nice of a place you take her has nothing to do with impressing her or giving you better results. You could take her for a walk and it could be good enough. It’s all about creating an atmosphere for getting to know each other in a more intimate setting. Dinner is NOT that setting. Like I tell my clients, the contents of a book is what makes a good book, not the cover.

If she doesn’t know that this is a date, I say you have your work cut out for you. But all is not lost. You can talk to her before the date and tell her about what you two will be doing. Maybe even go as far as telling her what she should wear (sexy would be a good word to throw in there if it calls for that). Just as when you like someone and you tell her that you do, the same thing goes for asking her out on a date. State it clearly and firmly and there will be ZERO confusion.

Pay attention guys and don’t make this mistake again.