How to Master the Art of the Compliment to Inspire Real Connection

Compliments are an all-too-often misused attempt at casting a rod to see if they bite. It's a great idea, in theory. But here I'm gonna explain why it doesn't work and how you can make a little adjustment that's going to feel really good to you regardless of where the connection goes.

So, you're at your favorite coffee shop standing in line and behind you walks up this human who's got eyes you could dive into, a smile that's making you melt, and hair that you'd like to see in your bed tomorrow morning.

First of all - you're not gonna say all that. Second - you don't even know if they're single! But - you just can't possibly wait in this line with such proximity to an opportunity without at least trying. So what do you do? Energetically cross your fingers and offer a complement -

You: "Your hair is amazing." 

Attractive Human: "Thanks." Followed by a slight smile and a short, uncomfortable laugh.

Most people will just leave it at that.

But if somehow you muster the confidence to say something else, the only thing you can do is kind of awkwardly un-transition into another random comment or question.

You: "This is my favorite coffee shop." 

Attractive Human: "Yeah, it's good."

AAAAAaaaaaaand awkward again. Just turn forward, shut up, and wait for the barista to save you from yourself. 

Ok, maybe you think I'm exaggerating. Maybe this approach has "worked" for you. But I would define it as working only if you're truly feeling the vibe of mutual connection between you and the person. And if it's turning into spending more time together, then awesome! Continue doing it! 

BUT! If you find that your compliments are falling flat - it could be because of some of these common reasons:

1. The person feels on the spot, threatened, defensive. Their sympathetic nervous system has come on line which creates the fight/flight/freeze response. So, the person will...

  • fight by objecting with "Oh, no, it's so dry and frizzy."

  • flee by deflecting with "Yours is awesome too."

  • or freeze by not knowing what to say or do and thinking silently, "What does this person want from me?"

2. The complement is not revealing of YOU [even though, you might think it took guts to go up to them]. This person is either feeling on the spot like the description above OR maybe they hear this compliment often. Oh, and you don't make it better by saying, "I'm sure you get this all the time..."

3. It’s a statement that doesn’t have any conversational leverage. There’s no real jumping off point for further deep-dive, awesome discussion.

So, here’s what to do about it!

How to give a compliment that actually goes somewhere...

  1. You notice something about someone that is attractive to you.

  2. Feel the impact it has on you. What's the energy or vibe you feel from this person because of that thing you noticed? 

  3. Get in your body and out of your head. Getting in your head will make you tighten up and not say it or say it weird. Take a breath, feel your feet, tune into your heart, whatever works for you.

  4. Say it, damn it! Tell them what you noticed and how it impacts you. So many times, people get so close to saying something and then, BAM! The other person picks up their phone, changes direction and is gone from your life forever. FOR-EV-ER! So, let’s not be so melodramatic. You’re a perfectly imperfect human just like the receiver of your compliment. So, go for it!


  • Check in with yourself to make sure you’re giving the compliment because you’re so inspired to give it. Like, there’s simply no other option than TO say it.

Why? Because the difference between motivated action and inspired action - if we’re motivated to act, we have an agenda or some external outcome we're looking for. When we’re inspired to act, we have an embodied impulse that’s gonna feel good to express regardless of the outcome.

Also, most people on the receiving end can smell “agenda” or “hitting on you” energy very easily. So, rather than focussing on trying to pick someone up, say the compliment because you’re inspired and it just feels good to you to say it.

  • Make sure to tell them what you noticed by using an "I" statement as opposed to a "you" statement. i.e. don't say, "You are stunning." "You are smart." "You're a really good dancer." These are arguable statements and put the spotlight on them. If you say, "I see you as smart" - that's YOUR opinion. It can't be argued. If you say, "I see you as smart, and it makes me feel inspired." Now you've revealed yourself too.

  • If you're about to say it and all of a sudden your shoulders are up near your ears, your ass is sweating, and your ears start ringing - you’re probably in fight or flight. That's OK! Preface what you’re about to say with how your feeling about saying it. You can straight up say, “I’m feeling a little nervous saying this, but I wanted to tell you that…”

This is a great example of how all that hype about the power of vulnerability can come into play. Being vulnerable like this indirectly tells the person - I'm honest, I’m human, I’m not here to intimidate you, and I’m sensitive to my emotions. By saying a preface like that, it’s also telling your body that you're paying attention to it, that you're not trying to override your system, that you're not judging, denying or repressing your feelings. You're honoring your sensitivity while also honoring your desire to connect with someone.


Chris was behind a girl in line at the grocery store and noticed she had neon pink and blue streaks in her hair. It was shaved on one side and spiky on the other.

Instead of saying, “Wow, your hair is so cool” [like she hasn’t heard that like 10 times today]. He said, “Wow, I feel playful and fun just looking at your hair.”

The girl’s energy completely shifted - her body perked up, her eyes brightened, and she smiled big as she launched into her story about how one day she was wearing a neon pink and blue shirt that made her feel more playful and she thought that if she dyed her hair the same way then she'd feel more playful everyday no matter what shirt she wore. She didn't even think of other people feeling more playful, so she was ecstatic to hear Chris' response.

Her story revealed so many other jumping off points for conversation had Chris wanted to connect more. 

And this is the type of thing that Chris and I experience on a weekly basis. We're not looking for dates or other partners, so maybe the lack of pressure is part of why it's so easy and natural and fun for us. We've started many conversations like this which have turned into beautiful friendships. 

We hope you'll take this as a guide, make it your own, and start connecting more in person than relying on online dating or letting people you're curious about pass you by. You've got this!