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October 2025

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Line of Questioning
Featured Article

Line of Questioning

Exploring the things you should—and definitely shouldn’t—ask when you first meet someone you’re interested in hooking up with.

Dissect any situation where a chance encounter with a fine piece of tail went from a casual conversation to a coitally charged romp, and it becomes painfully evident that first impressions are everything. Had it not been for the way the introduction unfolded, everything else would have gone to shit. The wrong lead, the wrong line of questioning, can almost assuredly make the difference between the average man getting laid or going home to jerk off into a sock. 

The problem is, not a heck of a lot of dudes understand that their first impression leaves a lot to be desired and their initial line of questioning’s got them seriously striking out.

On a recent episode of the Diary of a CEO podcast, Vanessa Van Edwards—the brains behind Science of People, which teaches folks how to sharpen their communication skills—opened up about one of the most common icebreakers: “So, what do you do?” On the surface, it sounds harmless enough. Certainly less offensive than inquiring about a woman’s cup size—”Wow, I haven’t seen a pair of D’s like that since my high school report card”—but Van Edwards says it’s a flat-out  conversation killer. 

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