Ask Your Wingman

Multiple times a week, I see this girl at the train station. She’s really cute and we’ve had eye contact a few times. I just don’t know how to go about approaching her. A train station seems kind of random and if I approach her all of a sudden, wouldn’t it seem weird or creepy? I guess the good thing is that my time is short since my train comes before hers but still, I have NO idea how to go about it.

Well if you two have made eye contact and she’s acknowledged you, the only alternative I see is to go right up to her and say this.

“Hi.”

Introduce yourself and get into quick conversation. She knows why you’re approaching her so if she responds well, then you know that it’s on. It may not be meaningful conversation at first but you two are talking and that’s what’s important. If you feel good about it, ask her for her number so you two can continue the conversation outside of the train station.

I have been seeing this girl for a while now and we’re really into each other. We’re pretty exclusive and I really want to take things to the next level physically. Every time we see each other, we only end up just making out. I want to have sex but I am not sure if she’s ready. What do I do?

Well, she could either be shy or not ready. The only way to truly know is to take the lead and see if she stops you. Take your time of course in terms of escalating things and if she responds well to you being a little more aggressive, then you know you can proceed. She may be hesitant and want to see if she can trust you. If you can prove to her that she can trust you with giving herself to you then you’re good.

If she says no, that’s fine too man. The whole saying, “no means no,” is actually a little untrue. I prefer to think of it as, “no means not now.” If she’s into you then it can’t be a total shutdown. Just be the man, take initiative and don’t come off as needy and desperate for sex. For her to want to have sex with you, you have to prove that you will take care of her and that you’re not in it just to have sex (even if you really are).

People tell me all the time that I am emotionless and hollow. I am not the kind of guy that smiles a lot and I am not a rambunctious and overly energetic person. People tell me that I have no passion and it hurts. I have tons of passion about life and what I do but I just never seem to show it. As a result, it hurts my relationships because women tell me that I don’t care about them and that I am unresponsive, which couldn’t be further from the truth.

I need to get out of this situation so that it doesn’t affect my relationships. What can I do that will get people to believe that I have emotions and am passionate and energetic and happy?

I used to be like this too. Women perceived me as very emotionless, cold, callous and unresponsive. Sucked to hear that when I consider myself to be one of the most passionate people that I know. The problem was no one could see it. I was keeping it ALL inside, subconsciously not sharing it with anyone. So I did a few things that made a world of a difference. I’ll share two that I think are important.

Smiling. For a little bit, I faked it because I didn’t know how to smile – as silly as that may sound. After a while, it got easy – especially when people started to smile back. When you smile, you bring energy and people can see your happiness.

Putting your emotions to words. That’s actually easier said than done but if you take your time and try it out, it’ll get easier the more you do it. Just don’t be afraid to say how you feel. Just being able to tell someone what you are feeling and what you’re thinking to will have a meaningful impact, believe it or not.

In order to be better at communicating, especially in a relationship, you have to be able to convey your emotions verbally and with body language. A guy like you is hard to read and while although it can be an attractive quality to some, eventually, women will want to be able to know what’s going on in your head.

My question is pretty simple to word but very hard to figure out for me. When is it reasonable to start dating after a breakup?

The answer is just as simple to word and just as hard to figure out.

Whenever you feel ready.

I can’t give you a timetable because everyone is different. Some people bounce back quicker than others and that’s fine. You and only you determine whatever time is acceptable. You’ll know when you’re ready. I can’t explain it, but something just clicks in your head.

In the meantime, my words of encouragement would be to not take too long moving on after a breakup. Time doesn’t stop and it will not let you go. Learn from your past because it’s what brought you here but don’t let it hinder your present because then it’ll hurt your future.