Engaging Conversation

Have An Engaging Conversation When Going On A First Date With A Man

You’re at your favorite restaurant with your best friend, and you spot that adorable twosome on what is clearly a first date. You grin and stop your own conversation just for a moment to eavesdrop.

They like each other, you can tell. And their words flow so naturally. Before getting back to your own chat you think, “Wait a minute, I’m a good conversationalist, why don’t my first date topics spark?”

Do you want to know the secret? Know him. You can do this, and here’s how.

Have An Engaging Conversation When Going On A First Date With A Man


Do walk into your meeting place as if you already know him

What makes you a welcome first date is a way you connect with him when you first meet. Give yourself permission to pretend you already know him. It makes you safe, easy to be with, and comfortable.

Do greet him as if the two of you are already close to each other

How would you address your date if you two were already in a caring relationship? You’d be casual, friendly, relaxed, connected, and genuinely happy to see him, right?

Do ask the question you would ask if he was already your man

Once you’re settled at a table, ask the first question: “How was your day?” or “What happened today?” Or: “What happened to you this week?” You would ask this type of question to a friend or loved one.

Ask it here, it breeds familiarity and it puts him at ease.

Do listen

Actively listening tells him you are receptive, and you actually care about him as a whole person. It’s a way to be engaging, and start the ball rolling without all the pressure. After, “How was your day?” the conversation is organic.

You listen, he’ll start talking, and before you know it, you’ve learned a whole list of things about him like what he cares about, and what’s important to him – right from the start.

Do keep listening

He just might tell you everything you ever needed to know, if you’re willing to listen and not interrupt to change the subject. And he will tell you without you ever having to ask.


Do not interview your date

We all hate the interview. Hate is not too strong a word here. You hate it. He hates it. It’s the line of questioning we ask so we can judge if he can measure up to our (high) standards.

If you’re still unsure what is meant by interview questions, here’s a sample: Since we know we can’t ask, “How much do you make?” we’ll ask, “What’s your title?” and “How many people do you supervise?” We’re not fooling anyone – skip the interview.

Do not bring out your checklist

Let things unfold naturally. Learn about this interesting new person in front of you, without ticking off the boxes of compatibility.

Do not talk about how terrible it is to be single and dating

He knows. He’s in the same boat as you are. Your time is better spent focusing on what’s working, and what’s worthwhile. Instead, talk about things that make you happy.

Do not justify why you are single

Assume you two are both singles for a valid reason. You can learn what happened in past relationships when you two know each other better. The first dates are for finding out what’s important, what he cares about, who he is, what he’s up to, and the sharing of entertaining stories.


Feeling comfortable with your date creates a willingness to share, and offers a sense of grace in partnership from the moment you meet. This is an important quality for a man who’s interested in a committed relationship.

Source: Wendy Newman via expertbeacon.com
Photo Credits: ©Kirill Kedrinski – Fotolia.com; Check Man, Cross Man and Jump Man ©ioannis kounadeas – Fotolia.com

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