Ask a Wingman: Making the Move and then some…

It was 12:47 in the morning. I had been suffering from a brutal hangover from the previous night (fucking free martinis). For the first time in 24 hours, I decided to get out of bed and go to see someone. Now in any normal circumstance, if I were to receive a call or text around this time, it would mean one thing and one thing only.

When you get that first text, you already know what’s going on and what may happen. After that, you make the decision and you commit to it, knowing that’s what the two of you want. But is THAT always what you want?

For me, it wasn’t.

Of course, it would be great to answer a booty call, but one thing that I have learned in my current year of being single is to NEVER judge a book by it’s cover. EVER.

Let’s rewind…

I met this girl in another city at a party and the way we met was what I would call…perfect. I call it perfect because when you go out and you want to meet someone one of the following things can occur:

She does or says something that opens the conversation for you, whether by making fun of her or complimenting her. Obviously, when you make fun of her, be playful and not blatantly mean. Too many guys out there take it WAY too far. Smile, laugh and never sound like you’re serious.

There is a situation going on where you can approach and talk to her about it. For example, a fight breaks out, or the DJ’s music selection. I like doing “situational approaches” a lot. It’s fun, natural and authentic if you really have an opinion about the situation.

You are in the zone and can feel like you can approach anyone at any time, without fail. This is pretty self-explanatory. Your confidence is at a peak level and you give two shits about the outcome. All you care about is having a good time and sharing your value and experience with others. If you can do this on a consistent basis, you will be a man in demand.

Ironically enough, as I was talking to a friend of mine, she walked by and accidentally stuck her finger in my drink. She didn’t have a chance of getting away. My first words were, “Really?”

She felt embarrassed and I continued to poke fun. She wanted to buy me another drink and I refused and I decided to take a sip from my drink. It made her feel better and then I believe I said something like, “well, since we are sticking your finger in my drink, I guess I should know your name.” She introduced herself and from then, it was great. Come to find out, we were both from out of town and she lives in the same city as I do. We made plans to meet up when we were both back in the city. We saw each other a couple more times while we were down there and both times were fun. I was excited to see what could come out of this when we were back in the same city.

Now fast-forward…