The Bad Behavior On Dates That Ruins Your Chance Of Real Connection

No date should resemble an interrogation.

Asking these questions on a date, ruin your chance for real connection pics five | Shutterstock

We all know that communication is the core of successful relationships. But how do you create meaningful conversation and dialogue when you're just getting to know someone?

Men and women often tell us that on early dating experiences — first and second dates — they feel as if they're on the witness stand being interrogated by a friendly but persistent prosecutor. Yikes! Not attractive.

What is it about our culture that leans toward this method of starting conversations? (We all seem to do it.) We're not sure, but we encourage an entirely different model for our clients, a model you can use in all of your relationships. Stated simply: On a date, or with a mate, don't interrogate.

@lifepartnerbykclee A date should not feel like an interrogation or reading an autobiography. If it feels like this person is grilling you incessantly about your past when you’ve only just met them, feel free to exit the date when you’re comfortable to. No one has the right to interrogate you about your past, especially early on and dating. Similarly, if your date continues to talk about themself and goes on and on and on and doesn’t even bother asking you questions about you and trying to get to know you as a person, then feel free to exit the date when it feels right. Someone who expects you to just sit there and listen to their entire life story without even caring to understand you deeper, shows you that they're a narcissist who just wants a listening ear and nothing more. If your date starts to feel like either of these scenarios, then it’s your full right to exit the date if you’re not enjoying this person’s company and not having a good time. . . . #datingtips #datingadvice #datingcoach#baddates #foryou ♬ original sound - KC Lee

RELATED: 5 Questions To Never Ask Her On A First Date


Are any of these questions familiar conversation starters for you?

  • Where are you from? (Code: What is your background?)
  • What do you do? (Code: How much money do you make?)
  • Where did you go to school? (Code: Do you meet my standards of a well-educated person from an elite social position?)

In our culture, we ask these questions freely. But did you know that in Europe, for example, these three questions are rarely asked? They're considered rude and intrusive because they are essentially questions about social class. Not very personable, is it?

Other popular questions we ask on early dates include:

  • Where do you live? How long have you lived there?
  • How many siblings do you have?

If someone's divorced:

  • How long have you been divorced?
  • How often do you see your children?
  • Where do they go to school?
  • Where does your ex live?
  • When did you start dating again?

For those who never married:

  • How is it that you have never married?
  • Why are you still single?

For widows and widowers:

  • When did your spouse die?
  • How did he or she die?
  • When did you start dating again?

RELATED: The Conversation That Will Ruin A First Date Every Single Time

So, what's the problem with this approach to asking questions, especially on first dates? After all, you're trying to get to know this person, right?

The flaw in this sort of questioning when you're trying to get to know someone (or even when speaking with someone you already know) is that these questions shift responsibility for the interpersonal agenda from you to the other person. You base the conversation on your needs, and the other person (who now feels put on the spot) must do the work of choosing what to say to meet those needs.


It's not a dialogue, nor is it a conversation. This way of relating truly is a one-sided interrogation. It's about what you want to talk about and what you want to know, and they end up feeling forced to prove themselves to you.

We propose a different method of creating dialogue.

Instead of asking questions, make declarative statements about how you feel. Tell your own story and let the other person respond freely, instead of starting a conversation by questioning them. Remember when we asked our kids (or our parents asked us), "How was school today?" The answer was always, "Fine." Or, the classic, "Where did you go?" "Out." "What did you do?" "Nothing." Charming conversation, don't you think?

So, the next time you are on a date, first or even fifteenth, try: "This is one of my favorite restaurants because its view of the river is just beautiful. I always feel so good when I come here." With this personal statement, you then provide your date (or anyone you're with) an opportunity to chime in with how they feel about the restaurant, the food, the river, how close the restaurant is to their home, and more. 


They can now decide which direction the conversation goes, based on how they feel about what you said. Statements of elaboration then organically evolve from a mutually uncovered topic: ("Yes, I came here with my children on my son's 18th birthday." "Really? I always celebrate important events here, too!"). And there you go, real conversation is born.

You can spark great conversation with statements about yourself and how you feel at that moment. Once a conversation begins, then let non-intrusive questions flow organically. You ideally want questions of interest and elaboration. Questions like, "Is it hard to get reservations during graduation week?" or, "What's the best thing on the menu?" feel fine.

RELATED: Woman Shares 15 Crucial Rules She Follows To Guarantee A Successful First Date

Can asking the right kinds of questions help you fall in love?


A New York Times article from 2015 cites a psychological study by Arthur Aron, which attempted to make people fall in love by asking 36 "intimacy-building" questions of each other. Some are mild: "If you could have dinner tonight with anyone in the world, who would it be?" Some are more intense: "Do you have a secret hunch about how you will die?"

In the research, the hypothesis was that "mutual vulnerability fosters closeness." In the findings, it turns out that the volunteers did feel much closer to their partners after asking those questions. The difference in why those questions worked is that they are not interrogations; they invite mutually agreed self-disclosures.


So, on your next date, try saying something not about yourself, but from yourself. Make yourself vulnerable and invite that same openness from your date (or spouse or child). Once you're fully engaged in true dialogue, questions become friendly, open-ended, and more like tell me more, rather than the obvious agenda-pointed, how do I know if you're worth my time?

We're confident that you'll discover natural dialogue, and the personal stories that follow will make the conversation better and far more interesting for you both.

RELATED: 36 Questions To Ask Someone You Want To Fall In Love With

Peggy Wolman is a coach and matchmaker, and her husband Dr. Richard Wolman is a Harvard psychologist and author of Thinking With Your Soul. Together they help singles of all ages find (and keep) true love.