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How to Avoid Awkward Date Questions and How to Respond if Asked Them.

Woman with a drink contemplating how to respond to an awkward dating question.

The Third Degree Will Not Get You the Second Date

While I don’t usually have calls with clients on the weekends (though, I still do work… dating never sleeps), when a client frantically texted me tonight to talk about a date (I’m writing this on a Sunday evening), I knew it was a call I had to take.

She started by saying that after she got home from a first date last night (this one happened to be in person, but the same would apply for a video date), she cried for an hour. What could have been that bad? Apparently, this was a set-up, so her friend knew both the guy and my client and thought they might be a good match. She walked into the bar to meet him (some cities are at partial indoor capacity these days), and she said he immediately started peppering her with questions. At first, they were innocuous enough:

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?

Then they got downright intrusive:

·       Why did your last relationship end?

·       Why do you want to be in a relationship?

Am I wrong? Is this how I am Supposed to Date?

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.

At the end of the story, she said to 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, whether you’re meeting in person, online, or over a video chat for five minutes. 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.

Expert Tips on How to Respond

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.

·       I worked hard to move past that, so I’d rather not go back there right now.

·       Once we get to know each other more, I’d be happy to share a bit about that.

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.

About the author: Erika Ettin is the founder of the online dating consulting service – A Little Nudge – helping people find success online through photo selection, profile creation, date planning, and more. Find out more here: