The Fine Art of Conversation

 It’s no secret that most successful men have well-honed conversational skills. The ability to express thoughts and ideas efficiently projects the image of a self-confident, intelligent and witty individual. For those who are good at it, conversations are engaging, comfortable and they seem effortless. In addition, good conversationalists make others feel interesting, clever and valued.

Within the context of a date, the lack of good conversation skills is often a deal breaker. Make no mistake – her perception of you will be shaped by how well you are able to communicate with her and others. And while some people have a natural gift of gab, most good conversationalists have to work at it. This involves planning and an advance knowledge of your audience. If she’s agreed to go out with you, I hope you’ve had at least a few verbal exchanges with her. If you listened to what she shared, you will have plenty of subject matter to discuss.

Most conversations can be broken into three parts: Small Talk, or the superficial back and forth involving pleasantries, environment and inquiries about events or others; Purpose, the actual sharing of opinions and ideas between parties, and Integration, which is merging the ideas of the parties into a satisfying end or resolution. After a good, conversation, both parties walk away feeling connected and fulfilled. (see conversation skills)

Helpful Hints: 1) Ask open-ended questions, 2) Be relaxed, and 3) Take cues from your location

The Underappreciated Art of Listening

Nothing says “I’m interested” more than active mental involvement while your date is speaking. This requires maintaining constant eye contact, occasional head nods, indicating engagement, and verbal confirmation that you understand. It’s easier than most men realize. According to Dale Carnegie, most people like to talk about themselves, and they find you more likeable, or charming, when you let them. So all you have to do is get the ball rolling, sit back, and really listen to her.

Let her tell you about herself, allow her to share her opinions and discuss topics that she enjoys. But you have to be sincere. Don’t just act interested. You have to be interested. If she’s talking about potting plants and you are having a hard time remaining involved, direct the conversation toward another one of her interests where you can be more engaged. While listening, take occasions to paraphrase points and opinions to make certain you will remember the gist of the conversation when or if required, and ask clarifying questions as required to deepen or broaden the discussion. (see conversation topics)

Creating a list of Fallback Topics

Until you become great at conversation, there are things you can do to help yourself along. One of these involves creating in advance a list of topics you think she might like to discuss. Maybe it’s her job, her family, her pet, her ambitions or her favorite movie or book. It can be a mental list, or you can write it down on a small scrap of paper. Try to list at least five fallback topics, specific to what you know about her. That way, when you come to a lull in conversation, you can simply start at the top and work your way down.

Subjects to Avoid

A date is no place for a passionate discussion on politics. You are trying to discover and appreciate the best about each other. But unfortunately, most people are at their worst when spewing deep-seated political convictions, whether it’s from a soap box or from the gutter. With religion, keep the Bible closed. There is nothing wrong with sharing that you go to a specific place of worship and that your faith is important to you. But you must remember that over human history, millions have died over religious differences. Never air religious differences on a date. And as a rule, don’t argue with her about anything, even when you think she is wrong.

Sex and the Ex

Don’t bring up sex, don’t bring up the ex, and never bring both up in the same sentence. Let excitement flow in the undercurrent, but if you start up a sexual conversation, you’re taking a big  risk. The same discussion that you think is titillating might turn her off as sounding perverted. And don’t brag about your sexual prowess. She’s heard it all before.

As for the ex—be honest. You can explain your dating history and let your date know how and when the last relationship ended, but don’t dwell on the ex. In fact, it’s best not to mention her name or go into any detail about her. If you have children together, you should explain your role as a parent. (see ask men)


Women appreciate fun, and by extension, guys who can be funny. Unfortunately, we can’t all be spontaneously witty and entertaining, but a little pre-planning can help. Can you tell a joke? Do you even know one?

Comic relief is exactly what it is, relief. If you’re serious all the time, you come across as boorish and wet-blankety. Smile! Laugh! Say something funny every once in a while. If you need help, you can always contact me, or better yet, work with us by booking The Perfect Date. (see how to be funny)