Musings from the Mailbag: Keeping it Fun

by GK on January 14, 2011 · 2 comments

It’s Mailbag Time, boys and girls! And this is my favorite kind of mail, because it asks a good question AND strokes my ego. It’s from a former SF student of mine:

“Hey GK. I’m floored that it has been a year since you and I went out. I found it a fruitful experience which just keeps building. My game is rapidly improving and I no longer fret when things go wrong or not the way I wanted.

However, I have a question that I would like you to answer in a future post. This is really lame but I feel I would like some tips (aside from the big four) on making the conversation go from going well to fun and interesting but before sexual — those little “punches” to the proverbial balloon to make float up again.”

Lame? Certainly not. One thing guys often get wrong is the idea that they’re supposed to entertain the girl. What matters more, in my experience, is entertaining myself first. If I’m having fun with the conversation in my own way, even if it seems improper, chances are she will too. Or, she’ll think I’m a jerk and leave, which saves me time.

I was out drinking last week with Tre Tre and a female friend of mine in a quiet bar, and we were making all kinds of dirty jokes out loud. We had a game where every time one of us said “balls” we all had to drink, and we were wondering out loud where we could find some prostitutes.

You don’t have to be as obscene as us, of course. But because we were having such a blast, we were drawing others into our conversation. The girl bartender loved us. And I assure you, we weren’t trying to please anyone but ourselves.

Ultimately, you’ll want to find what works best for you through trial and error. But I’ll go ahead and give you some ideas of what’s worked for me and other guys:

When the conversation starts going sour, just look to Stevie.

Inside jokes: One time I was on a bar patio with a friend of mine, and Lord knows why but for some reason we were talking enthusiastically about Stevie Nicks.  I just turned and mentioned how mind-blowingly awesome Stevie Nicks is to a couple of blondes standing next to us, and they joined in. My friend and I got paired off with the two girls, and Stevie Nicks came up repeatedly during our conversation. I was so over-the-top enthusiastic about the subject that I’d even hold her in my excitement.


Another example would be the time I was winging for a student and within 60 seconds of meeting my girl I told her with great enthusiasm that I was producing a porn movie and asked if she’d like to help. That became a running joke between us, and because I showed an uninhibited side, she asked me how to say “take your clothes off” in Armenian, which became another running joke.

Teasing: And I don’t mean negging. This is where being a good listener is important, because girls will reveal all kinds of little flaws about them. If she tells you she’s bad with directions or can’t cook, now you have something fun you can bring up repeatedly.

Talking about unique stuff you’re into: Lately my Nerd Nite friend Bart has gotten me hooked on the hipster sport of disc golf, and I can’t stop talking about it. So naturally it comes up in my conversations with women, many of whom haven’t heard of it and get interested. It even gives me the excuse to demonstrate by holding her arms and simulating a throw. Everyone wins.

Another example would be the weekly Man Dates I have with Tre Tre. Girls often enjoy accusing me of being gay, and I have a lot of fun making innuendo about myself. Sometimes you want the girls to tease you.

Bringing other people into it: L.A. Greg and d.R. did a great job with this when they were coaching in a group situation. While talking to a girl or girls, they might send one of them on a fact-finding mission. Greg might say, “You see that girl over there? I want you to find out what her favorite food is and come tell us.” And sure enough, she’d do it with a big smile on her face. Then Greg might go do the same thing and come back.

Observing your surroundings: Pay attention to what’s around you, and have some fun with that. One time I’d met a girl at a museum event, looking at the women walking around us, and we surmised that the girls wearing high heels were single because they wanted to impress more. So each time a girl walked by, we’d comment on that.

Technology: This isn’t my thing as I don’t even have a smartphone yet, but I’ve seen guys use Youtube videos or funny apps with girls, such as the one that takes her picture and adds 150 pounds to it.

I could go on and on, but you get the point. Go where you have fun and talk about stuff you have fun with. That’s usually all it takes.


1 andy January 15, 2011 at 5:45 pm

greg… i just read dirks blog..
have you heard it? ..

2 GK January 16, 2011 at 1:31 am

I just read the blog today. I’m as shocked as everyone else. I’ll have more to say about it in a day or two.

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