Pro Tip #4: Try Conversation

We hear a lot from many single women (and even some single men) about first or second dates gone badly because no real conversation or communication happened. The problem seems to fall into two broad categories; the guy can’t seem to speak or can’t seem to listen.

red logo ibilThere are guys who can chatter like crazy on-line, with their friends at work, or in school. But put them in front of a live human being of the opposite sex and suddenly they are completely unable to ask a question, answer a question, describe a personal experience, or give an opinion on much of anything. Then there is the guy who on a first date can’t stop talking about himself and can’t even pretend to be interested in his date. It’s all me-me-me- my job, my friends, my parents’ messy divorce, my ex-girlfriends.

But any way you slice it, can’t seem to speak or can’t seem to listen equals failed dates. Good people are missing out on friendship, and maybe something more because their natural ability to hold normal two-way conversation fails them at the very time it could do them the most good.

Here are a few suggestions.

Make a plan.

Spontaneity is a fine thing, but you can’t always count on it. If you are a guy going on a first date with someone you don’t know well, spend a little time thinking about what you might like to say and —just as importantly —what you might want to ask your date. Don’t second-guess or over analyze everything you might want to say or want to ask. What would you want a new friend to know about you and what would you want to know about them? The point is never to take spontaneity out of the conversation, but help it along with a little thought before hand.

Location, location, location.

If you are dating someone for the first time, spending that first hour or two in a very noisy or very crowded place is not going to help you get to know each other. Meet someplace —at least for that first hour together —, where you can hear and be heard. It also shows your date you put a little thought into your relationship, even before it has begun.

Mental prep.

How are your own emotions or attitudes affecting your ability to hold a conversation on a date? If you feel some extra stress or apprehension going into a first date, face that fact ahead of time. Don’t deny it, but don’t give into it either. This is an emotional balancing act. Many guys will tend to freeze-up and have a hard time making easy conversation, or chatter away because they are scared to death of an awkward pause in the conversation. Don’t be either of those guys and make up your mind ahead of time you will not. One more thing, if you have a case of nerves and can’t seem to shake it, don’t have that extra drink or two to relive the stress and loosen up. Buzzed or semi-drunk is not attractive.

Be humble.

Some lucky souls don’t have stress or apprehension about first dates. They have interesting jobs, interesting hobbies, fascinating personal histories, and deep personal philosophies about life. If you even think you could be one of those guys, or if an ex girlfriend has said something leaning in that direction, take the hint. Exert a little humility and self-discipline when explaining yourself and your life to your date. Being confident and self-possessed is one thing. That’s attractive. Being a self-absorbed bore or on an ego trip is not.


Good two-way conversation means you have to be fully present and in the moment on the date. Judging from war stories about failed dates,this is not as easy or as obvious as it sounds.While you are with your date, pay attention to her. Pay attention to the expression on her face. What is it telling you? Put away the iPhone. If you see some friends, say hello, but don’t desert your date while you have a conversation with a pal.Sounds like pretty simple stuff, and it is, but many women refuse a second date because a guy spent half their first date with his pals at the bar or checking messages.

If communication and conversation has been a problem in your dating life, try applying these ideas and let us know how it works.

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