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There’s more to Deep Thoughts than meets the eye. The first thing to understand is that it is pretty direct. She knows why you’re there right away. It’s to flirt with her. There is no other reason for a man, a stranger, to tell an attractive woman she looks like she’s thinking deep thoughts. The chances that she will think that you are simply making an observation is close to zero. The reason that I like deep thoughts is that it plausibly allows me to start reversing the power dynamic very, very quickly. Here is how it breaks down:

Me: “You look like you’re thinking deep, deep thoughts.”
Her: “Me? No, just tired. Going home from work.”
Me: “So you have no story for me?” (First hurdle. In other words, “You have nothing interesting to tell me?” Already starting to set up the reversal of the power dynamic.)
Her: “Nope. No story.” (And sometimes:) “You have a story for me?”
Me: “Well, I did read an article that said that we spend on average 14% of our lives thinking about things we’re not going to do.”
Her: “Makes sense. Probably more for me.”
Me: “Oh yeah? You’re a dreamer. When I read that article, I said to myself, what would I do if I could have that time back, and I decided I would make a list of the hundred greatest novels and make my way through the ones I haven’t read.” (Pause) “What about you? What would you do?” (Second hurdle. She hasn’t thought about this. Her answer is likely to be less interesting than mine.)
Her: “Hmmm. Don’t know. Would have to think about it.”
Me: “Yeah, you think about it. Take all the time in the world. Meanwhile, what do you do now? Do you sing, do you dance, do you read, do you write?”
Her: “I’m in marketing.”
Me: “Marketing. You said that like it’s not something you’re thrilled about.”
(etc., etc.)

So the true power of Deep Thoughts is not that it hides your intentions. The true power of Deep Thoughts is that it get across this sense that you’re curious but you’re not completely sold. She knows right away that you’re there to flirt with her. What she’s not sure of is whether you think she’s otherwise worthy of your attention. It’s an opener full of skepticism and challenges, and women find that kind of interaction very attractive. I like it because I think it takes about three minutes for her to make a judgement about you, whereas telling her she’s cute basically gets an immediate judgement, a judgement based entirely on your looks and body language.