How to Shift the First Conversation from Awkward to Awesome and Leave Him Wanting More (Online, on the Phone, or in Person)

Feb 22, 2018 | by: Raeeka Yaghmai
114 Comments

Ah, that first conversation with a man who you don’t know from Adam is nothing short of awkward. I get it: all of a sudden you’re in a container called “dating,” and you gotta figure out if he’s the one or not.

All these questions are percolating in the back of your mind… Who is he? Could he be the man? Could this be the right person so I can just simply get on with my life and stop the exhausting dating thing? Is he marriage/long-term material? Is he the right match? I hope he’s the right match…I’m so tired of going on date after date! God, let him be the one… and the list goes on.

I seriously wish there was a button like one of those “Enter” buttons on our keyboards that we could just hit and the right man would appear! But unfortunately, finding love doesn’t work that way.

Like anything in life worth having, finding love requires our investment: time, energy, attention, resources, etc.

Based on Dating with Confidence’s philosophy of dating, you are the C.E.O. of your love life, meaning you get to be the Chief Experience Officer! So changing that first contact from awkward to awesome is 100% up to you. Here are four ways to help you make that awkward first contact with a man into an amazing experience for both of you, be it on phone, in an online message, or in person.

1- Keep your expectations in check
Here’s the reality for those of you who love facts and real talk: if you expect that you will magically connect with someone during that first conversation and it’s all based on luck, you’re setting yourself up for disappointment. Manage your expectations. Instead of expecting magic, create the magic by being curious to learn about this new man without judgment and by understanding that he, like you, might be very nervous and have his own set of 100 questions in his head. So be compassionate.
This ties in to points 2 and 3.

2- Be aware of judging
I totally get that as smart, savvy and ambitious women, you want to have answers and you want to have them now. But that’s not how dating works. Dating uses the exact opposite skills to create success. The best way to really know a man is to give it time to let him show his truth and his real colors. It’s so easy to go into dating being judgmental about a man: picking on every little thing and making up a story about it and thinking that you have the answers so you can make a quick decision. But what you’re really doing is making a decision based on your stories rather than a decision based on reality.

Instead, replace your judging with curiosity. Get curious and decide to learn about him. This is the step that so many smart women miss because they want to be safe and they want to make sure they don’t miss any red flags. So instead of being curious, they get all judgy and go in with an imaginary brick wall around them to protect themselves, and time and again I’ve seen women sabotaging their love lives by letting the good man – the potentially right man, who is a quality, relationship-ready man – get away.

3- Be compassionate
Be compassionate toward him. He could also be just as nervous about the whole dating thing as you are. The more compassionate you are, the more energy flow the conversation can have (and it can be lighter). Basically, you are creating a safe space for both of you to experience each other; and the safer it feels, the more you leave him with a good impression of the connection. Being compassionate in no way means to be easy and loose! It means being kind and caring—the exact qualities I’m guessing you would want a man to have. 🙂 Model that.

4- Ask open-ended questions
One of the best ways to get to know someone is by asking open-ended questions. This way, you’re not interviewing him but rather asking questions that allow him to express and explain more in his own way. An open-ended question is a kind of question that doesn’t ask for a Yes or No or one-word answer. Questions like “Do you have a job?” or “What do you do for a living?” are *not* open-ended questions. Instead, ask things like “What are you passionate about in life? What are some of the things you love about your life now?” These are open-ended questions. They allow him to respond in a way to share more, and so you get to know more about him. When you ask open-ended questions, the conversation goes from being like an interview to one filled with curiosity and learning about each other.

Now, following these tips doesn’t mean you will magically turn him into Mr. Right. But by making that first connection a pleasant experience for both of you, you will ensure that a potential right man doesn’t get away and that he will be able see you and not miss you just because that first connection was so awkward.

Bottom line is this: in an initial connection with a man, the safer you make it for him, the kinder you are, the less expectation you have, and the more curious you are to learn about him (rather than labeling him or comparing him to your ex), the easier it is to connect with him and learn who he really is. And that is the purpose of dating.

As always, I wanna hear from you. I wanna know the biggest insight you’re taking away from this blog. Leave a comment below. And if you enjoyed this blog, join Dating with Confidence’s FREE and PRIVATE Facebook group, “Dating Tips for Savvy Single Ladies,” where you can have more personal interaction with me and get support around your love life. And share this blog with your friends.
To your dating success!

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