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

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

By Catherine Muss

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 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!

Catherine Muss is a freelance writer based in Waterloo Region. She has a Bachelor of Journalism from Ryerson University, and she would have minored in psychology if she’d taken the “right” psych classes, but she took the fun ones instead.

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Chantal Heide - Canada's Dating Coach
Chantal Heide - Canada's Dating Coach
Chantal Heide is an Author and Motivational Speaker, focusing on dating and relationship building. Her books Dating 101, Comeback Queen, Fake Love Need Not Apply, No More Assholes, After The First Kiss, Fix That Shit, Say Yes To Goodness, and Custom Made (available on this website, Amazon, and your favorite online book retailer) help her readers attract the love they're looking for, regardless of their starting point . View her BOOKS page for more information. Be sure to check out more free advice on Facebook, YouTube, and Itunes, as well as fun tidbits about her life on Instagram and Twitter.

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