Dating Tips
For Men

Comfortable Conversation: It's between two but it starts with you

December 20, 2012
▪ 2 mins read

Perfect scenario

Every date you went on would end with you feeling like you just connected to someone with fun, sincerity and meaning. You will be enjoying a cup of comfortable conversation and feel relaxed in each other's presence. 

But if you don't get the conversation to back you up, even if you open all the doors and splash out on champagne there will be no connection.

So, what gets you over the fence?

What makes a good conversation?

The thing to know is (and I’m going to put this in bold because that’s how important it is)


The conversation you have will impress her, but the way to get there isn’t anxiously pre-planning all the amazing things you’re going to spew out across the table. You’ll probably end up appearing disengaged or even self-obsessed even if you’re just nervous. The key is being confident enough in yourself to be open and express your thinking. If you achieve the right mindset then the conversation will come fluidly.

That’s why it’s important to do a little homework before it comes to the big final. If you focus on creating an interesting life for yourself and feel awesome about what you’re doing, you’ll naturally want to share that and be excited to hear about others experiences.

When you’re talking to your date, really focus on engaging with who she is as a human being, and listening, rather than going through the motions. That’s what’s going to make you worth her time. When someone listens and is interested in what you have to say, it makes you feel good about yourself and that’s what will make her come back for a second date.

Basic breakdown, what you’re looking for is:

  • Dreams/ ideas for the future
  • Motivators and past experiences
  • Thoughts, feelings on people


So, say you were talking about work, you’d want to discuss:

  • What steps lead her to do what she's doing.
  • Not in terms of formal qualifications but what life experiences influenced her path
  • What makes her feel that she should be doing what she is doing?
  • Is it what she always wanted to do or when did it change?
  • What her ideal job would be/ what her big dream is
  • What does she feel about her colleagues, which ones does she gel with, what happened at the office Xmas party, does she think she wants to stay there?

The good conversation comes from interesting, comfortable people. The results of understanding yourself and what you stand for in life. Think of it in terms of `you’ll grow good flowers if you start with healthy soil’.

If you want to get more detailed tips on great conversation, don't hesitate to reach out to me!

Hayley Quinn smiling profile
About the author

Hayley Quinn is a leading dating and relationship coach, with 3 million views of her TEDx talk and 18 million YouTube views. She is spokesperson for Match, a columnist for Cosmopolitan, a regular contributor to international media, and has been published by Harper Collins (“The Last First Date”, 2022) and Simon & Schuster (“Do This, Not That: Dating”, 2023).

Stay connected with Hayley
Newsletter icon
By clicking “Accept”, you agree to the storing of cookies on your device to enhance site navigation, analyse site usage, and assist in our marketing efforts. Privacy Policy.