First Date Conversation Tips Do’s and Don’ts (with Video)

First-Date-Conversation-TipsA lot goes into meeting someone new. Even more stressful sometimes is that dreaded first date! Online Dating could mean a lot of first dates and first date after first date you get frustrated, but what if you had some fail proof methods of leaving with your pride intact? In addition to looking good, what comes out of your mouth is even MORE important. It really is all about asking questions that teach you something about the person, how they really think, what makes them tick and not the usual “where do you live”, “where do you work”, “where are you from”, blah blah blah. We’ve all been there, done that! Being well prepared could mean the difference between securing that second date or never getting a chance!

First Date Conversation Tips 

First Date Conversation Tips “Do’s”

  • Make eye contact
  • Listen actively & ask clarifying questions about what they’re saying
  • Think before you speak
  • Have topics ready (current affairs, your aspirations, what are you passionate about)
  • Be natural (be yourself)
  • Open ended questions

Sample good questions:

  • What’s the time of day you enjoy most & why?
  • Where have you travelled that impacted you the most & why?
  • What accomplishment are you most proud of & why?
  • What’s your favorite childhood memory?
  • What’s the best & worst meal you’ve ever had?

First Date Conversation Tips “Don’ts”

  • Don’t look around
  • Don’t talk too much or cut the other person off
  • Don’t overshare
  • Don’t check your phone
  • Don’t use closed ended questions that require “yes” or “no” answers

Sample questions that aren’t recommended:

  • How much money do you make? How much are you worth? What do you own?
  • My ex [insert baggage here]
  • What do you do?
  • Why are you still single?
  • I just hate [insert complaint here]

I recently spoke on CTV Ottawa Morning about First Date Conversation Do’s & Don’ts … click here or on the picture to watch the segment!


READERS: What are some of your First Date Conversation Tip Do’s and Don’ts? Share your experience and knowledge in the comments below!

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. I think it’s important just to go with the flow. I didn’t talk about exes but most guys brought up what they were seeking. One guy told me he was seeking marriage and another guy told me he wasn’t. I didn’t see either guy again but at least I knew where they stood because I was seeking marriage. I think though discussing current events can be bad if it is political.


      • True if people are respectful but the problem is many people are so rigid in their views and it may cause a fight. Then again I suppose it’s a good thing to see if peoplr agree on the important issues.


  2. I like the idea of having topics ready to but the problem with first date conversations is that you may have run out of things to talk about since you would have already have a few phone conversations. And I’m not opposed to talking about work, it’s where you spend most of your waking hours so I fully expect people to talk about work and there kids if they have them.
    Me person I don’t like to talk too much about my kids because I think it sends the message that I want you meet them in the near future when the focus should be on the two of us.

    I think asking why someone is still single is a fair question IF it’s asked at the right time. It’ll give the person the chance to come clean on some dirty secrets at the beginning like if she’s looking for the “perfect” man or if he spends too much time on fantasy sports leagues.


  3. As a man, let her do most of the talking. You don’t want to come across as a person that constantly talks about himself. Now, with that said, don’t let her just sit and talk talk talk. Keep a good balance and keep it flowing. Keep eye contact and don’t check out other women.


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