Dating is exciting! It can also be a little bit nerve-racking. We become animated over the prospect of getting to know this new person, but end up worrying about boring our date, running out of things to talk about, or letting the dialog run dry.  Often we doubt our own ability to keep the conversation flowing while on a date, especially when dating someone new. These are valid fears because these things can happen if you let them. But you don’t have to let them and you won’t have to worry so much about this because we are going to give you a quick class on effective listening, conversation direction, and creating intrigue!

Most of the time we are only half listening during a conversation. The other half of our mind is developing what we actually want to speak about or what we’re going to say next because we are not so much listening as waiting for our turn to talk. This is one of the prime culprits in creating conversational dead-ends. Listen. When it becomes your turn to talk, you don’t necessarily have to reply or comment on the original conversation topic. Instead, if you were listening, a whole plethora of conversational avenues will reveal themselves.


Pay attention to the syntax. There are always keywords being stated that act as the algorithm you need to never run out of things to say.  The internet refers to evolving conversations as ‘Threads’, but I like to imagine that someone’s dialog is like a street. There is the principle road you start on, but there are many well-defined markers showing you where you can turn off to travel down a different route. Here is an example of something your date might say:

“I work in consulting. After college, my friend John and I started helping people we knew with their projects and small businesses in our spare time.”

Now your date just revealed several things about him or her and you could continue down the exact same conversational avenue related to your date’s work or you can ask about some of the things they mentioned. For example, here are a few conversational avenues that you could take:

1.     “Where did you go to college?”

2.     “How long have you known John? Tell me about your adventures together.”

3.     “When you started out just helping people, were you doing it for free?”

4.     “What’s it like running your own business?”

There are dozens of statements or questions that you could ask regarding each one of these conversation markers … and the beauty is, if one dead-ends you can U-turn down another road that was previously marked. If you originally diverted down ‘College Avenue’ and it runs its course, follow up with, “So tell me about your relationship with your friend, John.”

Your date won’t mind changing gears, these were things that they brought up and it proves that you were actually listening; and now you are very subtly directing the conversation.

Remember, with each new avenue, you can decide whether you are the driver or the passenger meaning you are taking over and speaking for a minute or asking a question then listening. If you pay attention and navigate the conversational markers, not only will you never run out of conversation on a date, but there will be a natural fluidity to the give and take of the dialog.


Ok so your date is going well. The conversation is flowing naturally and you really like this new person. So how do you ensure that this person comes back for more … and sooner than later? The answer is Cliffhangers and Open Loops. You are going to learn to apply the same tactics that have been used in literature, television and marketing for years.

You see it every day. Television shows ending an episode with you dying to find out what will happen next week, a book chapter ending in a way that leaves you reeling to turn the pages for the next chapter, and open-ended bait click ads on social media that get you to click into some ridiculous website to find out useless information about this celebrity or that.

You can incorporate these tactics into your casual conversation to keep the air interesting and your date piqued and intrigued. Whatever cliffhangers you choose, just be sure that you’ll eventually be able to give a decent answer! Here is a classic example:

You say: “I just noticed something quite interesting about you. I wonder if anyone else has ever noticed this …” Then change the subject and avoid answering for a while or after they press the issue, tell them something like, “I’ll tell you on our next date.”

You can mix it up, using a couple of small open-looped cliffhangers to keep the intrigue going. They allow for chances to re-open that loop or “avenue” in the conversation. Then leave your date with a bigger cliffhanger that will make them eager to see you again. Ultimately, you should be able to ad-lib your open loops based on the individual and the dating scenario itself.

Now you have the tools to become a conversational expert, so there is no need to fear first date dialog. You can artfully steer the conversation in a natural and fluid manner and even leave your date hanging on your every word!

How about you? Do you have any other tips on conversation?  If so, leave them in the comments below.

Remember You can find the love you’ve always wanted and receive the love you deserve.

You just have to Take the First Steps Now!