How to Keep the Conversation Going on a Date

Last week I offered some advice on how to write an impressive first message. Hopefully you ran with it and are now knee-deep in the ladies. I also hope that  after charming them with your quality approach, you managed to keep the conversation going.

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If the chemistry is there, it shouldn’t be too hard, but even if the two of you are really into each other, the basic elements of discourse just don’t come naturally to some.

If this sounds like you, don’t worry. I’m here to offer you a few suggestions that will keep the dialogue flowing.

Ask Leading Questions

Try to avoid simple questions that require only one-word answers. Instead of “How’s your day going?” try something like “What did you do today?” You don’t want to pry or ask too many personal questions, especially if you’ve only started messaging, but you do want to give her a little something to run with.

Open Up a Little

The flip side of asking more detailed questions is that you should be prepared to provide detailed answers. I’m not suggesting that you should tell her everything right away. (She probably doesn’t need to know that you jacked off to porn last night, for example.) Just give her something to question you about or to respond with stuff from her own life.

Pay Attention and Respond

Don’t get so caught up in your own line of questioning that you fail to acknowledge her response. If she says something to propel the conversation in another direction, go with it. Otherwise she’ll feel that she’s talking with a robot. Nerves can lead to this kind of one-sided conversation, so just beware. If she takes things to a place you don’t want to go, just be honest and tell her you’re not comfortable with the question.

Keep It Casual

You don’t want to get too intense too quickly. Definitely follow her lead and don’t keep after her about something if she doesn’t want to open up. There’s a fine line between encouraging a good conversation and offering too much too fast. Try to joke a little, and talk about what you would like to do on your first date.

Go Easy on the Sex Talk

Even if the only thing you really want to do on your first date is don a pvc bodysuit and have her smear shaving cream all over your junk, you don’t want to lead with that. In fact, it’s kind of important that you let her get to know you a bit, and sometimes the excessive sex talk can get in the way of that. Even in you only want to meet for a hookup, be a gentleman about it. You do want to share your kinks early on… just don’t make that your primary focus.

Don’t Force It

Sometimes you can be doing all the right things, and she just won’t give you anything to go on. It’s frustrating, but there’s really nothing you can do. Don’t get angry or passive-aggressive. Don’t keep after her if she fails to respond. Just walk away. There will be plenty of opportunities to try out your stellar conversational skills.

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