Ask Your Wingman

We’re going straight to the mailbag this week. Next week, I’ll change gears and continue my series on life maintenance and talk about the social life, why it’s important to maintain one, even if you have a girlfriend and how to do it.

If you have any questions for me, send me an email at thomas@tsbmagazine.com.

There’s this girl I see when I go to my favorite bar. She works there. We greet each other every time. She’s really hot and I want to ask her out. What can I do without being creepy or weird because other than small talk, I don’t know anything about her?

Well, women who work at these kinds of places are paid to be nice. Not that it means that you don’t have a chance but I don’t want you to confuse her niceness as legitimate interest. If you know nothing about her and you are attracted to her solely based on looks, the only option you have is to ask her out for drinks cold. Just go in there, be bold, ask for what you want and if she thinks you’re cute, she’ll want to go out with you. Be honest and stand behind what you want. Just know her answer will be based on your looks, since that’s all she has.

I have an interesting question. Is it possible to be selective when it comes to finding a woman? I mean it’s pretty obvious that women are VERY selective and it’s socially accepted. Why can’t it be the same for guys? We deserve to be able to find the one that we really want to spend our time with, right? If we are selective, does that make us assholes? Curious to hear your thoughts on this.

Asking us if us being selective makes us assholes is like asking if women being selective makes them “bitchy.” Guys have just as much a right to determine the kind of woman they want as women do. The reason why this may be an issue is the perception of the pursuit.

Women are pursued, thus having to sort through the many guys who approach them. They don’t have a choice but to be selective. Men are the pursuers; leading them to fewer numbers that doesn’t make them seem as selective.

But in order to find the girl that you think is perfect for you, you NEED to be selective. It’s the only way that you are going to find a quality woman that you’ll want to settle down with (if that’s what you’re looking for). It doesn’t mean that you’re not allowed to have fun and meet many girls in the meantime but if you know deep down that she’s not a good match for you, move on and continue your pursuit. Never settle.

I have been with my girlfriend for nearly 3 years now. I can honestly say that we are awesome together and I am thankful for that. Why I am writing you is because she is going through some rough times and I don’t know how to handle it.

Over the years, my girlfriend wasn’t the best in staying in touch with her friends. Although, I thought it was ok that she considered me her best friend, I still encouraged her to continue to hang with her friends and even make new ones. Well it seems like her friends have had enough of her neglect and aren’t talking to her anymore.

She pretty much has no friends and it’s destroying her. All she has left are my friends and that’s not saying a lot considering they only hang out with her when she’s with me. She’s afraid to reach out to them because she thinks they’ll completely outcast her.

What the hell do I do with this? She’s in a world of hurt and eventually it’s going to seep into our relationship and I don’t want that.

Well first off, it sucks that your girlfriend’s friends deserted her like that. Makes me wonder how good friends they really were to her. I’m not going to say who’s to blame here because it’s not productive. Your girlfriend needs to go out and make new friends. She needs to build a life that doesn’t necessarily involve you. You can encourage her by taking her out to events or outings, help her meet people and branch out.

Be her wingman.

She has to make an effort to get and keep friends or else she is going to be alone. Her having you as a best friend is great and all, but what if you leave her? Then what does she have? You have to encourage her to make these changes because if you don’t not only will it affect your relationship, but also you eventually won’t be happy with her and you’ll want out. She needs to get herself together. You can encourage but it’s ultimately up to her.

I would like to consider myself a pretty confident guy who is ok with meeting and talking with women. There are definitely things that I could work on but overall; I’m a pretty social guy. I have a question about “having game.” Sometimes when I’m on, I can feel it and I feel unstoppable. Then there are the other times where I could have used it and it just wasn’t there. Is it me? Is it the women? I just have no idea. I am still in the process of understanding women.

One of my friends taught me a very valuable lesson when I was single and was having problems meeting women on a consistent basis. He taught me that the key to success (with women) is not worrying about the outcome and enjoying the process. At first, it made absolutely no sense but one night I wanted to go out because I had a shitty day and just needed to get out and distract myself. I really didn’t care about what was going on and I ended up having one the best nights of last summer that resulted in many dates over the next several days.

When it comes to “having game” and “being on,” you should know some subtle differences. When you’re on, you care less because, well, “you’re on.” Why should you care? If one woman doesn’t like you, why does it matter? There were 3 girls before her that liked you and 2 more than will like you when they meet you. You just care less.

When you’re “off,” your mind is spending more time trying to figure out why you couldn’t get with her and why you’re “off” than just having a good time. That results in you being more “off” throughout the night. But then again, sometimes the timing of connections can be wrong.

So to answer your question simply: When you think too much about it, you psyche yourself out and it becomes a “you” thing. When you’re having a good time and there’s no spark, for all intents & purposes, it’s her. Either way, continue to focus on having fun and not caring about the outcome.