How Do I Start a Conversation with That Handsome Man? Dating 101

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August 31, 2015
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September 8, 2015

How Do I Start a Conversation with That Handsome Man?                                        Dating 101

One of the most common questions we get here at Canada’s Dating Coach is, “how do I talk to men?”.

In preparation for the answer, I must first digress.

I spend a lot of time researching the dating world. There is a shocking school of thought everyone must behave the same way in order to meet a good man. I’m so utterly let down by my fellow humans who post advice like, “you just have to get over your shyness/insecurity/anxiety and push through”.

WRONG. That is bad advice! That is making light of someone’s personal struggle and telling them to ignore their instincts.

I can just imagine the kind of dating feedback a woman gets when she asks friends like these posters how to strike up a conversation with that cutie at the library. “Just go talk to him.”

If it were that easy, would she be asking for dating advice? *face/palm*

That’s the rant and here’s the advice.




The first step is to get prepared. One of the most common anxieties is that you won’t know what to say. Commit to memory 2 or 3 generic conversation starters.

Here are some suggestions:

Have you been here before?
What do you recommend?
How do you know the host?
Do you travel?
Read any good books lately?
What’s your favourite band?
What was the best part of your week?

Now collect some specific talking points. You’ll pull these out once the initial conversation has lulled. Get to know what’s going on in the world. Watch the news a few times a week, or at least catch the headlines on your favourite radio station. Chantal is a fan of setting talk radio to one of the dials in the car. You don’t have to be an authority on the subject, just have an opinion and be open to hearing someone else’s take.

When you see a man you’d like to speak with, catch his eye and smile.

It doesn’t matter if he’s with his friends or sitting alone. Did he smile back? Yes! Now is a good time to approach him and strike up some conversation.

Choose a starter that is based on your situation.

You do not have to start with your name and a handshake, but it works for me. Look him in the eye and don’t cross your arms, you will look relaxed (even if you’re nervous). And smile because you took that step! If the conversation lulls pull out one of those newsworthy items you read about this week. Choose something you’re interested in, “Did you hear about the Mars project that started this week?” for example.

If he gets going on a topic, don’t feel like you should interrupt and add a point. Be a good listener (on the other hand, if he interrupts you regularly or never asks for your opinion, recognize that he isn’t a good listener). He’s likely to say something that will give you something else to talk about, or ask about, and listening might give you a few minutes to settle your nerves. If he talks about something you aren’t familiar with, don’t panic. Ask him about it. Or if you’re really uncomfortable, change the topic.

Avoid questions that could be awkward such as what do you do for a living (what if the answer is “I just lost my job?), do you have kids (what if he can’t have any but really wants to?), anything prying or personal. This is an introduction, so save the personal stuff for later if it doesn’t come up organically.

Once you’re feeling comfortable with your conversation repertoire, practice. Chat up someone in line at the grocery store (“Oh that cereal looks good, have you tried that brand before?”). Say hello to the newspaper delivery person. Ask someone at the library for a recommendation. You don’t have to have a full conversation, just initiate contact and gain confidence. And when you see a man you would like to talk to, and you’re ready, smile!

There’s one more thing I want you to do: allow yourself to fail. I don’t mean fail on purpose, but rather take some of the pressure off of yourself by remembering that the only thing you can control is yourself. If you strike up a conversation with a handsome man and he isn’t interested or it gets awkward, that’s ok. Excuse yourself because you need to use the washroom/get back to your friends/call the babysitter/wash your hair. You will walk away. You can try again. But as you walk away please smile, because you took control and went after what you wanted!

Here’s what you can do going forward:

If he’s NOT ready to commit and you’re tired of this scenario, or just want to make sure your next kiss is with someone who’s ready, get a copy of No More Assholes and find someone seriously amazing and ready to commit. He’s out there, I promise.



If he’s ready to commit and it’s time to take it to the next stage (woohoo!), read After The First Kiss – 7 Steps to Making Your First Year Together Ridiculously Awesome  and make sure you’re creating a strong foundation together.

This is the book that helps you avoid turning little things into big fights, and you’ll love how the advice inside helps you create the Magical relationship you’re looking for. Peaceful, cohesive, passionate, and intimate.


Need help figuring the whole thing out? Let’s work together one on one so you can gain the clarity and peace of mind you need right now. My specialty is your peace of mind, and I’m adept at giving the perspective you need along with the tools you’ll use to start feeling happier, clearer, and on your way to the Love you want ASAP.


Look, nothing sucks more than giving your heart to someone who isn’t giving theirs back.


If this is something you’ve done too often it’s time to break that pattern, and lucky for you, you’ve met the pattern breaker. You’ll use different behaviors so you get a different outcome, and I know how to trigger a man’s brain in all the right spots.

Your happiness depends on your decisions first and foremost, not his, and I’m the Sherpa who carries the burden of knowledge and shows you the way.