Six Questions to NEVER Ask on a First Date

Enjoy this special post by guest blogger, Dr. Christie Hartman.

Dr. Christie Hartman is an author, behavioral scientist, and dating expert. Her most recent book is Changing Your Game, A Man’s Guide to Success with Women. Check out her website at

In this day and age, first dates have taken on new meaning. In the world of conventional dating – the world our parents and anyone born in the Baby Boomer era knew – there were fewer first dates and you actually knew the person you sat across from at dinner. But with the advent of online and mobile dating, going on tons of first dates with utter strangers is the new norm.

Simply getting into this new mindset can be a big challenge for many people. They want so badly to find someone they connect with and grow weary of meeting the wrong people. As a result, some develop a method for weeding out these wrong people as soon as possible.

What is this method, you ask? I call it the “Let’s cut the crap and get right to the serious stuff so I don’t waste my time with the wrong people” method. Advocates of this method look for reasons to rule someone out by asking difficult and personal questions right up front. Here are a few common examples:

  1. What led up to your getting divorced?
  2. Are you looking for marriage and kids?
  3. I’m looking for a serious relationship. Are you?
  4. Why/how did your past relationships end?
  5. What are your goals in life?
  6. Why are you still single?

Questions 1-5 are great questions. Crucial questions, even. However, they’re inappropriate to ask someone you hardly know, and have no business on a first date. And Question 6? That one is never appropriate, whether you mean it as “Someone your age shouldn’t be single” or “You seem too great to be single.” There is no good answer to that question. Everyone is single at some point in their life, no matter how great they are.

But I Don’t Want to Waste My Time!

Of course you don’t. You don’t want someone who cheated on their ex with the neighbor, isn’t looking for a serious relationship like you are, or has some other deal-breaker. But first dates should never be interviews, where you ask test questions and see if your date fails. By doing this, you not only rule out the wrong people, you rule out the right ones too. Why? Because even those who pass your test will hate being put on the spot by a total stranger, or will dislike their happy hour taking a turn down Serious Lane.

Remember: A first date, meet-and-greet, or impromptu meeting is an opportunity to get a feel for someone: Is she interesting? Is he polite? Am I interested enough to go on a second date? That’s it. Save the personal questions for people you’ve built rapport and trust with.



Filed under Date Etiquette, Meeting Up

6 responses to “Six Questions to NEVER Ask on a First Date

  1. I don’t mind if someone is curious about what I want from my life. My sense is that if the question is asked in a way which isn’t offensive or intrusive, I’m okay with it,,,,

  2. singlewhitefemaledating

    Reblogged this on Single White Female Dating and commented:
    Yes, I like this sound advice!! 😀

  3. Not George Clooney

    If you’re truly listening, a first date will tell you several of these 6 answers either directly or by inference.

  4. Enjoyed your perspective. My thinking here on this important area includes an emphasis on the idea that conversation about early childhood experience is important, as this has a substantial impact on one’s approach to dating and relationship. Cheers.

  5. Beth

    I met a guy online and after we spoke on the phone I agreed to meet him for dinner. After we ended our verbal conversation over the phone to talk about our dinner plans, he text me and said, ” Oh yeah, I forgot to ask you – 1) Have you ever cheated on someone. 2) Do you have any STDs 3) Has someone ever cheated on you?”
    I mean – come on! I haven’t even met you in person yet! Talk about “cut to the chase” 😦

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