CitySwoon Blog

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Attn: Single Men. Exclusive Dating Advice by a top male dating coach.

Hello gentlemen!

We are well into cuffing season and headed right into the holiday craziness. In all this chaos, sometimes we forget to get out there and try and meet new people to date. I know it can sometimes feel like another job and can be exhausting. But anything great is worth working for, right?
So in order to help you guys out, I wanted to give some quick, exclusive dating tips for you so you can hopefully find someone wonderful to hibernate with.

Entertaining conversations

#1 Stop asking logical questions!

Anytime we meet someone new, whether it’s dating, networking or any other way, we just seem to run through the litany of normal, getting-to-know-you questions. “What do you do? Where are you from?
Where did you go to school? What do you like to do on the weekend?” Ugh! We go through the same ones every time and it’s so boring and logical. And are relationships logical or emotional? EMOTIONAL!


So we should be asking emotional questions. Instead of “Where did you grow up?”, ask “What’s one of your favorite memories from childhood?” In order to answer this questions, they have remember a happy time. As they remember it, it makes them feel happy. And most importantly, feelings of
positivity and you start to entwine. She feels so good when she’s around you, that she wants to be around you, to feel good! Make sure there is only a positive answer to your question and make sure it’s specific enough to have a memory attached to it.

Get great stories!

#2 Stories are a great way to showcase your different facets.

When we get together with friends, we love to tell stories.  It may be about something that happened this week.  It may be something that happened years ago.  But it’s fun trading stories, “Oh that reminds me of a time I…..”

While stories are a great way to learn about people, they also give you the opportunity to showcase your best traits.  Men should have 3 archetypal stories: the Triumphant story, the Joyous story and the Embarrassing story. 

The Triumphant story should have you beating the odds some way.  Maybe you saved someone’s life.  Maybe you go lost and got unlost.  Maybe you hit the game winning run that one your high school championship.  It demonstrates leadership and tenacity. 

The Joyous one should be about a moment or time in your life with deep emotion.  It shows that you are capable of deep emotions as well as demonstrating that you can recognize those moments when they happen.  Also, these two sort of balance each other out with masculine and feminine energies, of which we should all have a mix. 

The Embarrassing story shows that you don’t take yourself too seriously, which demonstrates confidence.  It also gives her some VIP info about you that others don’t know, which creates a psychological bond of trust between the two of you.  After you have these three, add more about you.  If you’re a good cook, tell a story that showcases your cooking skill.  If you’re super spontaneous, spin a yarn where your spontaneity takes center stage.

Realistic, achievable goals – relax, be yourself and smile.

#3 Make sure you have the right goals set.

Imagine you go to a party and say to yourself, “I’m going to get 4 phone numbers tonight!”  It’s a lofty goal.  But what happens if you don’t succeed?  You feel like crap!  And it was your fault because you set the wrong goal for yourself. 

Instead, set small, easily achievable goals at the beginning to set yourself up for success.  “I’m going to smile at one girl today.”  Can you do that?  Of course you can!  And how are you going to feel when you succeed?  You’re going to feel good about yourself.  Then up your goal a little bit.  “I’m going to smile at 5 women today.”  Every time you achieve your goal, you feel good.  And when you feel good, you want to continue pushing yourself to win more goals. 

The GOAL is to become the most interesting, dynamic and fun person that ends up drawing people to you.  Imagine you walk into a room and there is a guy telling story and everyone is gathered around.  Where do you immediately want to go?  To hear the story!  And he’s not telling it in order to get the right girl, but, because he’s the kind of guy that draws people to him, he might end up getting a great girlfriend as a side effect.

Every party, every bar, every interaction you have has the possibility to introduce you to your future partner.  But dating is a skill set like any other.  You need to practice it.  So go to a speed date (a matched one with Cityswoon of course!) and practice, practice, practice!  That way, when you turn your head and see an attractive woman behind you, you’re ready!

By our contributor, Hunt Ethridge