How to Maintain Conversations with Women?

For over two years, I’ve had clients and the general population of men ask me the same question when it comes to talking to a woman.

“What do I say next?”

For many men, it’s a serious problem because not knowing what to say will inevitably lead to a whole lot of silence, even more awkwardness and an end to what could have been an amazing conversation with a really attractive woman. Some guys are becoming more and more comfortable with approaching and starting conversations with women and then they hit this roadblock.

“Ok, so I approached her and I got her to smile. She gave me her name and now she knows mine. Now what?”

Well, to really understand the answer, we have to really look into a couple myths and squash them once and for all.

Awkward silence is NOT awkward. Men (and even women) have this belief that silence in a conversation is a bad thing and feel compelled to fill it in with SOMETHING. I am here to tell you that it is NOT true. When two people make a connection, talking about something passionate or get into a serious conversation, there needs to be a time to have a “conversational exhale.” That happens when you actually need to sit and take in what just happened and soak it in a little. Some people will sit there in silence and think to themselves. Others may just jump into another conversational topic right away. Either way, this is another way to finds out about someone’s method of thinking and it can help you better connect. In the end, if there is silence (for just a few seconds), it’s not always a bad thing.

Conversation is mostly up to the man. Yup, I said it. Yes, one of the goals is to have her talk about herself and find ways to relate to her (and she may talk more than you throughout the conversation) but in the end, as the man who approached her, you are in charge to directing the conversation and determining where it goes. It’s as simple as that. To help yourself, think about some talking points that you’d like to mention. Your initial conversation with someone who could be a potential mate can also serve as a way to find out if she holds the basic qualities of someone who you’d actually be interesting in getting to know. So if you are into travel, make sure you bring up something about traveling, whether that may be flat out asking her a direct question,

“Traveling is such a major part of my life. Do you ever get a chance to travel?”

or you can just tell a story,

“It’s funny you mention that. I went to Jamaica a couple of months ago and it was such an awesome time. I got to try out this amazing fruit fusion drink and it had all of these fruits that I’ve never had before. I love being able to go to different places, experience unique cultures and try interesting food.”

Both can serve as a “test,” to see whether she possess that same quality. Because, if you are a traveler and she doesn’t like to fly, you two may not be to fully get along.

But if you are afraid to just randomly make a statement, you can also try this. The only disclaimer is that you have to do something that most men find difficult.

Listening to what she is saying.

It’s really important for you to listen to what she is saying so that you can easily be able to relate to her with your own statement. For example, let’s say you hear a song by Eve6 playing in the bar and you say,

"I like this song. I love Eve6.”

And she says,

“Yeah, I like this song too."

You can follow up by saying,

“You know, I saw them live once at the Hatshell in Boston. You would think that a band like that wouldn’t be a good performing group but they were awesome. Have you ever been to Boston?”

She may say yes, then you two can talk about places that the both of you have seen and what you thought about it. Or she can say no and then you inquire about two things.

A. If she likes to travel


B. If she’s seen a live performance.

Either way, by following up with what she is saying (even if it may not seem as much), you can create paths of conversation and directing it where you’d like it to go.

I’m not saying that it’s easy. Takes some time, listening and practice, but after a while, conversation will definitely get easier.

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