Conversations they’ll never forget

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July 2011

Everyone asks questions. But few people ask really good, well-thought-out questions. These questions force us to look deeper into ourselves. They can unearth information about ourselves we didn’t even know was there. All great conversations are built by great questions. It takes guts to offer them a conversation they’ll never forget. It will involve you asking unique questions. It will involve asking personal questions.


Blast past small talk

It’s important you blast past the small talk as soon as possible. Small talk gets you nowhere because it’s boring. Instead, dive in with questions that dig deeper into who they are. Their passions. Their values. Their secrets. Have conversations they’ve never had before.

Let them be the star

A person’s favourite topic is themselves. It doesn’t matter if they’re a powerful CEO or an Ordinary Joe, everyone has a story. Telling stories allows people to feel like their life matters, their opinions are valuable and that they’re special. Use the conversation to illuminate all the things that make them amazing. If they feel like a star talking to you, they’ll find you more attractive.

Speak up

Make your voice heard. Too many singles talk too softly. It doesn’t matter what you’re saying if no one can hear it. Be confident enough in your words to yell them over the roar of the stereo or crowd. Impress other singles with your boldness and vocal capacity.

Look them in the eye

Great conversations start with great eye contact. The eyes are the windows to the soul because they show your true interest and confidence levels. Keep eye contact with your conversation partner at least 70% of the time to assure them you’re confident and interested in what they’re saying.

Repeat their name

Once you’ve learned their name, slip it back into the conversation. This will develop some instant camaraderie despite the fact you just met them. People love to hear their name and are more comfortable around those who use it.

Master story-telling

Have half-dozen colourful stories you can tell. Have each practiced and perfected. Know what words to emphasize. Where to pause. When to hammer home the punch-line. This will allow you to weave one seamlessly into the conversation and appear extra interesting, entertaining and engaging. People love great storytellers as much as great stories.

Leave interviews to the police

What’s your name? Where are you from? Where do you work? Where did you grow up? When people answer these questions, the questioner often mistakes politeness for interest. Stay away from any question you were asked in your last job interview. These questions can be asked later in the conversation, after a connection has already been established.


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Say whatever pops into your head

Think before you speak. What sounds good in your head doesn’t always sound good when it escapes your lips. Give everything a sober second thought. Not doing so can wreck even a great conversation. Something witty can turn into something awkward, embarrassing or confusing if it comes out wrong. Save yourself some hassles and choose your words carefully.

The ex

People make the mistake of talking trash about their ex’s, not realizing it actually lowers their value. If you went out with an amazing woman – you must be amazing too. If you went out with flawed man – you must be flawed too. If you only go out with special singles, you insinuate you’re special and you won’t settle for anything less. If the topic comes up, complement the positive aspects of your ex and then add, “but it just didn’t work out.” Talking about failed relationships is everything but.

Switch personalities

If you’re loud and rowdy one moment and quiet and reserved the next, it’s going to put people off balance. Pick one personality. If you have multiple personality disorder you’re not going to do well in the dating world. Minor unpredictably is good, major unpredictably is scary.

Quickly switch topics

If you are discussing a topic they’re showing interest in, there’s no reason to change topics. If you don’t believe the topic will lead to a connection, slowly transition out of it and into a topic you believe can. Quickly jumping from topic to topic looks like you’re trying to win them over, not have a real conversation.


Talking about sex too soon does the opposite of what people hope it’s going to do. Instead of having them think about you sexually, they see you as sexually inadequate, a poor lover and sexually unconfident. The best way to broach this subject is suggestively. Sly words with a flirty smile. Dance around the topic. Insinuate. But never approach sex directly with someone you’ve just met.


Keep your wallet closed. People make the mistake of trying to show off how much money they have or brag about all the cool things they own. It doesn’t work – unless you’re trying to attract gold-diggers.


People of all political and religious backgrounds haven’t let their differences get in their way. Attraction, for most people, is based purely on personality. Unless you will only date people of a certain political party, religion or ethnic group, leave politics and religion out of the conversation. All you risk doing is alienating someone before they get to know the real you.