4 Keys to Having a Great Conversation with the Man You Like

Proverbs 20:5

Whether a guy approaches the woman or the woman starts a conversation with a man, many ladies struggle when talking with a guy because they lack some basic insights into the male mind.

So much more could be said, but these 4 points will really help you have a great conversation with the guy you like.

1. Men Want to Listen to You Talk More Than They Want to Answer Your Questions

Honestly, when a man meets a woman who gives long answers to his questions, he’s relieved. Even if you think you’re jumping all over the place and talking about random things he doesn’t care about, in most cases, the man is beaming inside. Why?

Because men are constantly working to keep conversations going with women. As the pursuers, men typically feel the pressure to lead the conversation. While I’m not saying you should lead the conversation, I am saying that you make his job a lot easier when you don’t hold back and you let your words flow.

Proverbs 20:5 states, “The purpose in a man’s heart is like deep water, but a man of understanding will draw it out.” When you open up and freely share your thoughts, feelings, and emotions, it makes this man feel like “a man of understanding” who was able to draw out those deep waters inside of you.

A lot of women make the mistake of asking a guy too many questions. I’m not saying you should never ask a question. If you want to know something, then ask it! And it’s certainly good conversation etiquette to be inquisitive, to reciprocate questions asked to you, and to ask follow-up questions to things someone just said. But just know that if you feel self-conscious about talking too much, you shouldn’t feel that way! The vast majority of men don’t want a conversation with a woman to be 50/50. They want to listen more than they want to talk.

Of course this is a generalization. There are some men who have a lot to say. But in most cases, a man would be happy to listen 75% of the time and talk 25% of the time. It takes the pressure off and makes him confident to approach her more often.  The more you talk to him, the more confident he becomes that you want to talk to him. This will lead him to ask more questions and to talk to you more too.

2. Ask Fewer Questions and Make More Inference-Led Statements

Again, don’t be afraid to ask questions. This advice is not meant to be legalistic. Rather, I’m referring more to emphasis and ratios. So rather than just asking questions, you want to mix it up. And one way to do that is to make inferences based upon what you already know about him.

Now it’s your turn to practice Proverbs 20:5, “The purpose in a man’s heart is like deep water, but a man of understanding will draw it out.” Sometimes making a statement about what you think a man is feeling will help draw out what is actually in him.

For example, it’s natural to ask a man what he does for a living. That’s not a bad question, but it isn’t great either. It’s pretty mundane. However, one way you can step it up is by assessing how he talked about his job and then making an inference like, “I bet your boss loves you. You seem like you’d be really good at being an engineer.” Or you could say, “I bet your boss has his hands full with you. You seem like the kind of guy who wants to lead rather than be led.”

You might be totally wrong, or you might nail it and be exactly right! But that’s what makes for an exciting conversation. If you’re wrong, he’ll correct you and say how he actually feels; if you’re right, he’ll confirm your assessment. Either way, a statement like this will elicit a response from him. You’ll be drawing out the deep things within him. You two are getting to know each other on a deeper level and in a much more interesting way than just asking questions.

Lastly, making an inference, even if you’re wrong, tells the man you’re really studying him, that you’re invested in getting to know him on a deeper level, and that you are not afraid to say what you think. It’s a sign of interest.

3. Balance Your Agreements with Disagreements

If all you do is agree, you’re boring. Also, too much agreement makes you feel disingenuous. It can make a guy feel like you’re just saying what you think he wants you to say.

However, if all you do is disagree, you’re annoying. You’ll feel contentious and he’ll assume you two are not connecting.

Enjoyable people have a way of drawing you in by focusing on your commonalities, but then keeping you engaged by retaining their own individuality. So you want to focus the majority of the conversation on the things you two have in common. But when you notice a difference in opinion, you should highlight it.

Proverbs 27:17, “Iron sharpens iron, and one man sharpens another.”

You might think disagreements would weaken the connection, and certainly, if it’s hostile or too often, it will. But when done right, disagreements actually help strengthen the connection because it will show this person you’re truly opening up.

4. Enjoy Yourself During the Conversation

As Howard Thurman said, “Don’t ask yourself what the world needs. Ask yourself what makes you come alive, and go do that, because what the world needs is people who have come alive.”

Similarly, it’s important not to just ask what a man needs in conversation. Rather, it’s important to ask what makes you come alive, because a great conversation requires two people enjoying life together.

Proverbs 17:22, “A joyful heart is good medicine, but a crushed spirit dries up the bones.” Emotions are infectious. The way you feel will influence the way he feels. The more you enjoy talking to him, the more he will enjoy talking to you.

While there are all kinds of tips and techniques that can help create a great conversation, there’s only so much you should try to do. In the end, the best conversations are those that involve two people who are naturally enjoying each other.

Therefore, while it’s important to think about the man you want to connect with, it’s just as important, if not more important, to actually pursue those topics of conversation you want to talk about. If his job is boring, don’t lean into that. If you’re interested in his family, lean more there.

One of the best questions to ask is “What do I want to talk about?” because a man wants to talk with a woman who seems interested in the conversation.

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