When to Speak Up (Or Shut Up) When You’re Dating Someone New

When to Speak Up (Or Shut Up) When You’re Dating Someone New

You’ve been dating someone new for a couple of months. You talk and see each other regularly, have a lot in common and you’re really really starting to feel like this could be something real.

Until he says something that eerily reminds you of your ex. Oh, you’re spending another night with your girlfriends? Ok, then…. and now you’re feeling all kinds of panic.

Should you say something or keep the damn thing to yourself? How do you know which way to go? 

When you’re not sure if you should say something to the guy you’re newly seeing, ask yourself, ‘is this a “me” thing or an “us” thing?’.

Allow me to explain.

You know that communication is important for a healthy relationship and you’ve been told that it’s not only safe, but necessary, for you to tell a guy how you’re feeling. 

Which is all very true. Hell, I’ve said these very same things to you myself.

And since you’re a successful, high-achieving woman, I know that you’re capable of adding another layer to this – a layer that could take you from “forever single” to happily ever after.

When you’re wondering if you should say something to a guy you’re seeing start to break it down to understand if this is something you need to look at and possibly heal from on your own, or if it’s something you need to work through with the new man in your life.

Ask yourself:

What does this remind me of?

Am I I’m projecting my past onto my present?

What are the facts here?

What insecurities does this bring up for me?

Is this something that I need to work through on my own?


Is this something I need to talk to him about?

Is this something we can grow from, together?

This is going to require you to be exceptionally honest with yourself.

You may have the tendency to shy away from tough conversations, and so you’ll opt for the DIY option. Or, you’re used to dumping the load on someone else – in this case, the new man in your life.

Try to put your habits aside and look at the situation with fresh and curious eyes.

Is this an opportunity for you to practice being honest about your feelings?

Or is this your “own” stuff (aka shit) that you need to deal with on your own?

Is it up to you to let this go?

Or is a clarifying conversation with him the way to go?

As you may have guessed it, there’s no black or white answer. 

There’s the answer that’s best for you, and it usually has to do with your growing edge – otherwise known as, the next iteration of you, the more developed “you”.

Yes, communication is important.

So is managing your own emotional well being.

You need to decide which is called for here. Otherwise, you’ll be talking till the sun comes up. Every damn night. 

Ask yourself the hard questions. Feel into your truth. And if you’re still feeling stuck, get in touch with me.

With love,


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