“Tell me about yourself”

The first real-time contact with a potential date can be awkward. You may have a sketchy description from an online profile, or just a few minutes of information from the friend who connected you. You want to find out more about him, but you’re not sure how to ask without seeming like you’re interrogating. So how do you ask?

There are many ways. But let’s start with a question that gets the hairs on my neck standing on end. It is the seemingly innocuous:

“Tell me about yourself.”

Why does this irritate me so? Because it is so brainless. It says, “I haven’t bothered to read or remember anything about you. So instead of asking you to tell me more detail about what I know about you, I’m asking the most inane question I can muster. I’m not very creative, thoughtful, or inquisitive.”

Equally inane ones are,

• “Why are you still single?”
• “Why did you divorce?”
• “Do you have kids?” (It says I don’t in my profile. You read my profile, right? I didn’t think so.)
• “Why haven’t you married?” (To someone who says he’s not divorced or separated.)

Here are some ones I’ve found more interesting:

• “What’s your favorite response to ‘Why are you still single?’ Now what’s the real reason.”
• “What do you feel you might have done to save your marriage?”
• “What’s your favorite part about being a dad?”
• “In your next relationship, how do you want to prevent whatever went awry in your marriage?”

There are myriad other questions you can ask which get progressively deeper and more revealing as you get to know him. The point is before you speak to him, think about some gently probing questions you can ask. Don’t be confrontational, but ask questions that get you to uncover values you find important.

Once I went out with a man who complained that his divorce cost him over $100,000, even though he’d just told me the marriage was over years before and they just stayed together for the kids. I asked, “If it was over long ago for both of you, why was she so acrimonious?” He paused for a moment, as apparently no one had ever asked that before. Then he said, “Probably because of the extra marital relationships.” I said, “Yes, that would do it!”

You can learn a lot not only by what a person asks you, but how he answers your questions. Try to make yours interesting, unusual and about issues that are important to you.

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