How Do You Have The “Where Is This Going?” Conversation

How Do You Have The “Where Is This Going?” Conversation


First of all, don’t. But do ask them on the first or second date what’s on their mind.

Let me clarify.

Asking a guy “Where are we going” implies you’re already headed into the future with him, and you want him to jump on board. That’s a scary notion for somebody who doesn’t know if you’re the person they want to advance with, and rightly so. Most people with common sense aren’t committing to people they don’t know (and neither should you). So asking “Where are WE going” can trigger a fight or flight response (did you notice how quickly he sat back in his chair with wide eyes!) because, in his mind, you’re not a “WE” yet.


So don’t ask him a question that seems to say you’ve already included him in your future plans. Instead, let him know where YOU’RE going, and then ask him what he’s planning for himself.

Here’s how that goes:

“Hey, I just wanted to say, I’ve had my playtime and that was really fun! But now I’m really looking for someone to have a relationship with. You know, start a family, buy a house, travel the world with. What about you?” Sit back, and let him answer. If he’s on that particular page in his life, he’ll simply concur. “Yeah, me too.” If he’s not, you’ll hear this; “Uh, well, I’m actually not ready for a relationship right now, I just thought I’d get out there and meet people, hang out, see where things go.”

And now you know where he’s at in his journey. Look, just because he went on a dating app and messaged you for a date, it doesn’t mean he’s in the state of mind needed to be a generous, long term thinker, AKA a Man. He might be “in-between relationships” and looking for companionship. Someone to hang out with, go places with, have sex with, and that’s it. And he actually knows that on your first date already.

So asking for clarity is key to helping you decide what YOU want to do. Are you going to stay around and maybe catch feelings for someone who isn’t currently sharing the same goals as you are? Or are you going to cut this one loose, and stay open for the Man who’s ready to find the one who wants what he wants in life? You know, get married to, buy a house with, have kids with, and/or travel the world with?

The choice is yours. Just don’t call him an asshole if you didn’t ask within the first few dates, then fell for someone who had no intention of being your life partner in the first place.

Here’s what you can do going forward:  

When you need a vetting process and you’re ready to make sure your next kiss is with someone who’s amazing, get a copy of No More Assholes and find someone seriously ready to commit. He’s out there, I promise.

Once 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.


Chantal Heide

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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