A client of mine recently was set up on a date through friends. She walked into the bar to meet him, and she said he immediately started peppering her with questions. At first, they were innocuous enough:

Where are you from?

What do you do for work?

Then, she said, the questions started to get a little deeper:

Do you like your family?

Do you want to get married?

Do you want kids?

What are your deal-breakers? And red flags? Both in you and in other people?

Where do you see yourself in five years?

Then they got downright intrusive:

Why did your last relationship end?

Why do you want to be in a relationship?

The more questions that came, the more she curled up into herself and didn’t know what to do. At one point, when she had already clammed up, he said, “A deal-breaker for me is that I can’t date an introvert,” as he looked right at her in her silence. The funny thing is that she is one of my more outgoing clients, but when put in this uncomfortable situation, she shut down.

She reached out to me, her coach, and said that she cried when she got home and asked me, “Am I wrong? Is this how I’m supposed to date?” I was sad that she felt the need to ask me this because she’s been on good dates before, and she knows that those are usually the ones where the conversation is organic. Instead of a litany of questions, there’s banter and laughter, both of which were absent on this date.

I assured her that, no, this is not how you should successfully date. I told her that it sounded to me like he had a checklist in his pocket or on his phone that he was going through, and he wanted all of the correct answers—at least for him—before he proceeded with any real conversation. Of course, I don’t think he had any malicious intentions. He probably thinks that he’s dating efficiently by getting all the “hard stuff” out of the way first.

But he’s wrong.

He’s scaring most women. Not because they don’t have answers to these questions but because he has only just met these women, so it’s not an appropriate time to ask such personal things.

My client was particularly struck by the “Why did your last relationship end?” question. As she’s told me in the past, it did not end well. And that’s a time of her life she really doesn’t want to go back to, especially on a first date with a stranger who is only asking to judge her for it. I gave her a few pointers on things she could say to that question next time:

- You know, I’m enjoying getting to know you, so I’d rather not bring someone else into the date.

- I’m really thinking toward the future, not the past.

- The last relationship made me a better person for any future relationship.

- Once we get to know each other more, I’d be happy to share a bit about that. (This is my favorite way to answer this questions, as it’s not a “no,” but a “not yet.”)

In the end, this was a bad date. Not because there wasn’t mutual attraction. But because he gave her a 100-question test, and she was afraid to get one wrong.

I validated her feelings and told her that what I want to come from this experience is for her to feel empowered enough to say, “Your questions are making me feel a bit uncomfortable. I’d love to just chat and see what we have in common.” As I explained it, he didn’t seem to care how his line of questioning made her feel (terrible), so why was she so concerned about how she might make him feel if she expressed her desire not to answer? If this situation gives her the courage to speak her mind, then it was a productive experience.

But, please, on first dates, stop with the questions. The third degree will not get you the second date.

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