• Alexandra Filia

First Questions, First Impressions, Making conversation on your first date

Updated: Mar 22, 2019

So, you met the man of your dreams and he is actually talking to you! Congratulations sister! Here is where you get to the next step or he politely drifts away. Unless you are a total knockout, you will need to get his attention and intrigue him enough to stick around.

Best way to do this is to ask him about himself and keep doing that. Marvel at his achievements, compliment him relentlessly and listen intently. Take a look at him and it may become quickly apparent what he is proud of. Does he look really fit? What is he wearing? Is it professional? Are his shoes shined? Does he have the latest phone? Any logos or other clues on his clothing?


Make some educated guesses and act like a professional sales person. What do I mean by that? When you start in sales, they first teach you how to observe the client. For example, when you walk into someone’s office and you see photos of his wife and children, compliment him on his beautiful family. If he is wearing a tie that looks like it was picked with care, compliment him on that; you get the picture, right?


Don’t make the mistake of half listening while you are thinking what you can say about yourself. Do not talk about yourself at all. Always steer the conversation towards him. As you are listening, look out for clues on the next subject. Did he say he has been traveling? Ask him where he’s been, ask for advice on places to visit. Cunningly align yourself with his interests by saying that it is your dream to visit there but you have not managed it yet. Keep asking questions looking for common threads. Be sensitive to subjects he does not seem to enjoy and quickly move on. If you manage to hit on his passion you have struck gold. Fan the flames and watch him fall in love.


When he goes home, he will remember the wonderful conversation he had with you and how wonderfully you made him feel. He will recall your time together as relaxing, inspiring and above all effortless. On to conversation number 2 on the next date. Use the time between dates to relentlessly research subjects that he raised and get up-to-date. Did he mention interest rates? The US election? Artificial Intelligence? Boxing? Learn, learn, learn. You will be the first woman he has met that knows so much about what he is interested in and can ask all the right questions. He will barely look at your outfit or the few extra pounds. Stars will be in his eyes! What an amazing girl you are….

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