“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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3 responses to ““Tell me about yourself””

  1. Sassy Avatar

    Wow. I try to keep it much lighter on a first day. No point in going over like what someone would have done to save their marriage at the first coffee. I feel like easy, impersonal things are a good way to break the ice and see if you’d like to get together again. And I don’t want to give out my personal insights about my life right away either. Thoughts? (BTW, I just discovered your site and enjoy it very much. –Dating again at 46

  2. Catherine Ann Avatar

    I really like this man at my school. He is my art instructor. I find myself constantly thinking of him and desiring him. He’s single and so am I. He is 58 , and Greek Orthodox ,and I am 52. Due to the ethics of student/teacher relations I tend to hold back with compliments or emotions. I did ask him for coffee in the past and he always had something on the agenda where he couldn’t accept. I recently ask him ” You wont hurt my feelings if you tell me the truth, do I make you feel uncomfortable for some reason?” He said “No, that’s not the reason, it’s just that I had problems in the past because of similar invitations by students, therefore, I have to be more careful”.

    He has given me signals all along that he find me interesting even though he doesn’t say it. Now, that I have him for the second semester and things are (very slowly), showing a bit of hope, a new student, a very attractive Black woman with intellect and charm,maybe about 55 years old has been connecting alot with him, especially since I have a Friday Watercolor class and she has HIM for all-day painting. Now that I have stopped to say hello to friends and HIM in the painting class, I’ve noticed a difference in his conduct. Last week he literally agnored me (most of the class had gone home by this time). I was so choked when I just couldn’t help noticing the attention he gave this woman. I had taken my chances to meet him at the elevatior to at least say goodbye, and there she was with him still. She gave me an intimidating look as If to say, “what do you want here??” I feel so awful and disillusioned. I have been so kind and thoughtful to him by giving him little treats and gifts all along because I have cared for him. Please tell me, do you suppose I still have a chance with this man? He is a decent man from what others that have known him for over 30 years have told me. It doesn’t seem like him to play hard to get with me . It just doesn’t. I need your advise and opionion on this. Thank You

    Ms. Catherine Ann

  3. Dating Goddess Avatar

    Catherine Ann:

    I’m afraid he’s sending all the signals that he’s not interested. I would let it go. You’re just going to bang your head against the wall. When you aren’t a student any more, you can try one last time for coffee, but it seems he doesn’t want to start anything social with students, as he’s had problems in that area before.

    So release this one back into the dating pool and keep your feelers out for another great guy!