Keeping the Interaction Light

[Ryan0802]

I've gotten pretty good at approaching, and essentially saying 'f***k off' to my approach anxiety since January (was my NY resolution). Gotten almost addicted to approaching. Worked drastically on my fundamentals the past year.
However, I keep hitting a new roadblock now...

Question: After approaching, how do I make the interaction light? How do I get out of work/boring professional mode? (I know when I'm in it & am at least able to identify)
I'm a CPA and entrepreneur; leaving me always seemingly 'tense' typically from being at a desk/mental tasks each day.
My most recent girlfriend has even told me to quit being a stick in the mud; said playfully, but deep down serious.

Question Add'l: How do I add humor? What comedians do you recommend watching, and what key ways do you improve your humor?
-It helps to have an 'role model' for me to watch
-Also I know humor isn't necessarily.. necessary.. but the girls I'm most attracted to respond well to sexual humor. Even use it themselves at times.

I have a very dark sense of humor, and the stuff that isn't dark is also a very subtle sense of humor only close friends get.
I want to redevelop this into something more sexual (drawing subtle attention to phrases), devil may careish, witty, and light that I can incorporate ON THE FLY. I just have no idea how to go about developing myself in that way - so any tips or past experiences would be incredibly helpful!

Ways I've currently been trying to address it: Watching stand-up comedy (Jim Jefferies, Andrew Clay Dice, & a few others - also re-watching Californication & watching Grey's Anatomy).

Thank you GC'ers, and best of luck on endeavors!

 

[Fuck This]

If it doesn't come naturally, it is hard to manufacture humor. I'm a pretty sincere person so I shy away from trying to "be funny". But what I have discovered is that the people I am around are pretty supportive and the mood stays light through mutual appreciation, and some self deprecation .

Try being complimentary about people's achievements. It is amazing how the mood lightens up when you tell people about the awesome stuff your buddy here just did. Then it progresses to ridiculous levels of fantasy all while shining a light on them .

"Jack here just ran a 10k with no training. He had the Kenyans looking over their shoulders, worried he was going to catch them!"
"Lee works for that Megacorp Medical company. Last week they had him presenting to the board on new security measures. He is gonna be running that place in 5 years. When he does, I call dibs on the first flight in the company jet!"
"Joe just got those awesome shoes. Aren't they cool? Next week when I get my paycheck, I'm taking him to be my fashion consultant! Then on to Milan for fashion week!"
"Matt was in China last week. He said it was for business, but I think he was keeping them from nuking Korea"

Another nice byproduct is that the "mutual admiration society" is awesome social proof. I tell my kids, "the more light you shine on other people, the more is reflected back on you."

 

[Ryan0802]

That's an excellent mentality and rule to follow. This I can easily start doing and implementing, as I already naturally try to give encouragement to others.

For ex. Acquaintance dead lifting at the gym today: "Dude, your getting up there in the weight. I'd love to just throw (if it was a girl 'play') around with that kind of weight."
"Yeah, but you weigh way less than me. You see your results in the mirror more."
"Well all that means is I pick up the girls ... then you knock me out and just take them "

Thanks for the help man!