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5 Bad First Date Questions… and 5 Good Ones!

By Andrea McGinty September 08, 2022 Dating

As I listen to my clients share weekly information about their dates, I’m often surprised at what they asked the person they met on a first date… or vice versa.

My take? Some of these questions reminded me of job interviews in my 20s. I thought, “Oh no, if you asked me this on a first date, I’d be out of there so fast!” How about this one: What are you looking for in the dating process? Great way to scare people. Too analytical. Too investigative. Too nosy. Too boring.

As a dating coach who communicates with many clients weekly, sometimes I nearly fall of my office ball when they tell me what they discussed. And then they wonder, “Hmmm, why no second date?”

In this article I will share the worst and best 5 questions for a first date that I’ve heard over the past few weeks from my clients.

5 Worst First Date Questions

What Was a Major Turning Point in Your Life That Got You Here?

Excuse me?! Aren’t first dates light, fun and casual? You’ve just basically asked: Tell me about your divorce, widowhood, bad breakups and everything in between. I believe you will agree this is intrusive and breaks every boundary of a first date.

What’s Your Relationship Like with Your Family?

You’re not addressing wedding invitations and trying to decide which weird sibling or uncle to exclude. Invasive? Yep! You’ll learn all this in time – be patient.

What’s the Best Date You Ever Had and Why?

Let’s leave this with a short: I have no comment on this one, except, perhaps, unbelievable?

What Have You Learned About Yourself from Past Relationships?

Yikes! This question will get you no second date.

When You’re Feeling Down, What Always Cheers You Up?

Well, you’re not his/her therapist. Do you really want to delve into something depressing on a first date?

5 Best Questions

If you’re really out of inspiration what to ask on a first date, here are 5 suggestions that always work to break the ice.

Are You a Movie Fan? Favorite Movie? Actor? Actress?

Always a fun topic as most people are back to the movies or at least streaming. One date asked my client “Top Gun or An Officer and a Gentleman?” Good question as Top Gun 2 had just come out, and she went with that.

He went with Officer as he thought the story about loyalty and growth was cool. She learned a little about him. As to favorite actress, they both chose Sandra Bullock and laughed. Definitely a 2nd date here!

So, What Do You Do for Fun?

Easy, engaging question. You’ll already know a bit about them from having read their profile – ski, SUP, tennis, opera, baseball games. So, it’s easy segue into a conversation. Note: You never have to have the exact same interests as you don’t want a mirror image of you, right?

What Do You Like to Read?

Almost everyone reads something – whether it’s the Wall Street Journal, People Magazine, Huff Post or National Geographic. One easy topic is books. Funny how quite often I hear fiction fans are attracted to non-fiction fans, and vice-versa.

Any Upcoming Vacations?

OK, who doesn’t like to talk about travel? This question generally spirals into favorite past vacations and bucket list thoughts. You learn much from a person who climbed Denali or a person who likes the Cayman beach – their idea of adventure and activity.

Where’d You Grow Up?

Many of us are not living where we grew up – this generally transitions into all the places a person has lived, their family and siblings, traditions, sports teams… just a fountain of information about your date!

Keep the tone light and fun! Enjoy the date and learn something new about the person you meet. One of my clients last week went on a date with a doctor who shared all his favorite supplements with her. While there was no chemistry, she learned quite a bit about vitamins!

Let’s Have a Conversation:

What’s your experience with questions on first dates? Have you asked or been asked one of the worst questions? What questions have sparked really interesting conversations?

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Jeanna Sandy

My only qualm with this is the question about family. I don’t want to get invested in a man that has no relationship with his children. If like to know that from the start.


I agree. However, I don’t believe I’d ever ask someone who I didn’t know very well, a question, worded in the aforementioned manner; “What’s Your Relationship Like with Your Family?”. I feel that mannerism can come across very judgementally. I prefer to ask my date if he had any children, or even if he has any grandchildren, and if so, just allow him to tell me about them, basically allowing the conversation to progress naturally. There really shouldn’t be anything wrong with asking if he has any grown children. And if the conversation needs help, which it usually doesn’t, but of it did, I’d probably just ask him if his children/grandchildren live here, or nearby (meaning in the same city or state where we are having our date), and if he gets to see them often. That would likely give me enough information to have at least some idea about his relationship with his children/ grown children, and ultimately, if I may be interested in getting to know him better, and see him for another date, assuming there were no other red flags, or deal breakers, and that I had a fun time.


Excuse me…..but sometimes the unthinkable happens and the parent is alienated from their children by a sick, demented, narcissistic, borderline personality control freak who is a master manipulator. One would not understand unless the person is in the other person’s shoes. It happened to me. And I’m the MOM! You just don’t know what’s behind the scenes unless you get to know the person first instead of making quick judgments.


Help me to understand if I need a dating coach?

The Author

Andrea McGinty is the founder of It’s Just Lunch dating service. She sold it and founded so she could help singles navigating online dating. In the 2020s, she knows the best way to meet people is through online dating using a professional coach and specializes in singles in their 50s-70s!

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