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Depends on the person. If you’re naturally good at improvisational chatter–situational can be great. I really like it. My issue is that I often know exactly what I plan to say–I just don’t open my mouth. I have this internal dialogue–part of me says “Say that–now!” the other part says “naaaaah—just walk on. Some other time”. Usually the last part wins out.

Once I DO open my mouth, I don’t have much of an issue moving into personal stuff–that kind of conversation comes pretty naturally. Some people are less comfortable with that sort of interaction. For example I don’t like opinion openers. I’ve gotten numbers from them–and even some dates–but that had nothing to do with the opinion opener–it was just my ability to transition.

Just like with this “direct” stuff–some people are really sexualized and ballsy–and that sort of thing plays to their strengths. I’m more easy going, so it doesn’t quite suit–unless I REALLY feel something.

That all said–I like “Deep thoughts”. I haven’t used it myself–well maybe something like it on occasion–but it’s a good way of saying “I’m going to flirt with you–and I want you to tell me about yourself while we’re flirting. If I like you maybe it can go somewhere.” Nice subtext.