Easy Ways To Have Deep Conversations And Get Guys To Open Up To You

Stephen Hussey

“Constantly talking isn’t necessarily communicating.” – Joel, Eternal Sunshine of the Spotless Mind

Every relationship begins with a conversation.

Every friendship is defined by a long string of experiences and conversations about those experiences.

Even every bout of meaningless, passionate, wild sex is punctuated by the odd dialogue about who you both are and what you are doing in the universe.

Conversation never stops being important. It defines how much you know about your spouse, how well you connect with friends and work colleagues, and how much you can influence and attract new people into your life.

There are many books on sub-communication and body language that like to pretend that the actual words coming out of our mouths hardly matter. I don’t believe them.

Like dull writing, dull conversation is stale, unemotional, cliché, routine, passive, and can trap you in a nightmare spawned from hell if you have no choice but to endure it.

The anticipation of bad conversation is the reason you wince and consider rejecting the call when that particular friend or family member’s name appears on your Caller ID. It’s boring because you can predict the entire conversation. The routine is stale and pointless – the conversation is going to do nothing except remind you that you would never choose to speak to this person again if you weren’t related by blood.

This also happens in our romantic lives. Here’s an imaginary but familiar conversation between a couple at dinner:

How was work?
How’s Bill?
Yea, Bill’s good.
Did you call the electrician today by the way?
Also we really need to get that new furniture sorted this weekend. Let’s go to the store on Saturday.
Ok. Have you decided on which sofa set you wanted yet?

The questions are pedestrian. The answers are flat.

This back and forth can bruise your heart and wrench the life from your soul if you endure it long enough. Two people can talk, but both of them can know nothing about what’s really happening inside. Because not all conversation is connection.

I think conversations can change, and even save our lives. The best conversation is about encouraging someone else to dig out their soul and offer it up for examination. Here are some easy ways to encourage them:

1) Ask questions that give someone permission to open up emotionally

People are begging to express themselves to somebody. The film director Kevin Smith said people have three needs: Food, Sex, and the Need To Be Heard.

But people will be scared to open up for many reasons. They’re shy. They’re frightened of your response. They’re British… Which is why you need to give them permission to emotionally express themselves.

The easy way to do this? Ask them how they feel about something. For example:

“How did it feel when you beat your record in the marathon?”

“Was it difficult to deal with your parents divorce?”

“What was going through your head when they told you that you’d got the job?”

These questions prompt reflection on emotion. They cut through logic and ask someone to search their feelings, which makes them instantly feel more connected. An excellent recent Huffington post article talks about a couple who recently incorporated these kind of specific reflective questions into their relationship. In one quote the author, Glennon Melton, explains: “Questions are like gifts — it’s the thought behind them that the receiver really FEELS.”

I couldn’t agree more. Great questions make someone look forward to a conversation with you, because you are letting them speak about subjects and emotions they don’t usually get to talk about.

2) Use the Sigmund Freud Method

When a guy is opening up to you, be almost clinical in your responses. Do not judge. Do not criticize or noticeably gasp when he tells you something embarrassing or crazy or bad that he did. Make him feel like it is perfectly normal, then show him more curiosity. In other words, just give the other person room to speak!

Psychiatrists have the skill of being able to let someone speak and ask questions to prompt them to dig deeper. Be generous and probe for him to give more: What was that like? What else happened? Are there other things you are worried/excited about at the moment? Had you always wanted to do that?

People tend to reveal themselves when they feel like they (a) have PLENTY of room to speak, (b) won’t be judged for their actions, and (c) feel like you are curious to hear their answers. Do this and people will instantly feel at ease in bringing any conversation to you.

3) Give them a chance to be an expert

People want to share their wisdom. If you want someone to open up, just ask for his advice about what they love. This goes especially for guys who are ambitious and have lots of life experience they want to share.

Ask things like: “What would you tell someone starting off in your work today?”

“What’s the most important thing you learnt about yourself when you lived in that country?”

“What’s your routine for keeping fit/healthy?”

These question are interesting because they tell you about a person’s inner beliefs and perspective on life, which then let’s you share your perspective if you agree or disagree. People think they have to know a lot about what someone else does in order to connect with them, but it requires no knowledge: just ask them to teach you or give you advice instead.

4) Reveal your own vulnerabilities

Don’t be a model of stoicism or people will feel distant to you. Show that you’re human by revealing vulnerabilities and foibles. Nothing that says I’m a mess, but enough to say I have flaws, and I’m cool with that. As long as you say them with a sense of humour to show that you don’t take it too seriously, people will love you for it.

If you try to be too squeaky clean and perfect, people will feel alienated by you and won’t want to open up for fear of looking weak in front of you.

5) Change your stock phrases

If you notice yourself answering questions in the same way all the time, get yourself to be more honest. Ask yourself: What’s my real opinion on this? Why am I hiding it? Am I trying to play it too safe here?

Push the boundaries a bit further every time and you’ll get used to communicating with more honesty. Try to iron out any phrases you seem to repeat in response to questions over and over again and give a refreshingly honest answer.

6) Get someone speaking about what they would love to do

Engage someone by talking about their dreams and the big picture. Ask them what they would most like to have achieved when they look back on their lives, or what they would like people to say about them in the future.

The future is great, because it’s easy for people to get excited about their upcoming plans and you’ll learn a lot about their inner ideals when you ask them about their dreams and goals.

A conversation can change someone’s life. We can affect people in profound ways with the right question, or a truly honest response, or when we allow someone just to get something off their chest that they have never been able to say.

The world might love to talk, but it doesn’t mean everyone is having worthwhile conversations. We have to always be the exception, the beacon of truth amongst the dishonesty, the magnet of what’s real amongst the posing and superficiality. We have a chance with every word, in a world full of hot air, to be a person who talks substance. Or at the very least, you’ll get invited to more parties.


Want More Copy-and-Paste Scripts To Attract The Man Of Your Dreams? Grab a Copy Of My Bestselling How To Talk To Men  program…

Photo credit: Benson Kua

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