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The idea behind Deep Thoughts is NOT that it always makes more sense than any other opener, especially a very specific situational opener. The idea behind Deep Thoughts is that the perfect is the enemy of the good.

Spending any time at all thinking about what to say – at the beginning or at any point in the interaction – is bad for you. Just the idea that you have to say the perfect thing, or at least something that makes sense to a total stranger is WRONG, WRONG, WRONG. Your approach should feel like you’re amusing yourself and that the girl is just a witness to this spectacle, not a key player.

Saying something random would also fit that bill, but then you have to work your way back to the conversation that is important to you, which is exactly what Deep Thoughts was designed for. Deep Thoughts is meant to get you into a thinking man’s conversation without stopping to think.

That having been said, Deep Thoughts happens to be a pretty good thing to say in almost any situation. When you say it to girls who are reading, they usually explain why they looked like they were really into their book (or the opposite – they tell you that they’re not really into their book). In other words, they interpret it as a look of focus or concentration. When you say the opener to people shopping, they usually laugh a little, as if they looked too serious for the task they were performing. For example:

Me: “You look like you’re thinking deep, deep thoughts.”
Her: “No, just looking for a box of cereal.”
Me: “Really? You look like the weight of the universe is on your shoulders.”
Her: (Laughter)
Me: “You know, I read this article recently that said…”

You’re mocking her a bit, which is good. And then you’re taking it right back to where you were going.