I’ve grown very fond of experimenting with vulnerability in dating. In my last long-term relationship, on our very first date we shared some of our biggest insecurities. I shared my wavering, expanding faith and how it was new, uncomfortable territory. He shared his insecurities with not acting like the person he felt he was deep down. It was refreshing to be able to share the areas of my life that I struggled with the most, right off the bat, to a person that I barely even knew. It was open, exposing and counter-intuitive. It gave me an incomparable high to be the person who spoke up first about the taboo, socially unacceptable topic of insecurity.

It’s not uncommon for me to coach women who don’t feel that comfortable with people they’ve been dating (or married to) for 5 years or more. The passion for sharing their deepest weaknesses is gone…if it was even there to begin with.

Here’s the truth: vulnerability is the catalyst for self-growth. Always.

I start all relationships, platonic or romantic, with a foundation of vulnerability. Not only does this allow me to feel more freedom emotionally with said person but also it gives them permission to claim the same space. I take down my guard and share what I wish wasn’t so about myself, uncovering the ugly, the judgmental, the shame, and the guilt so that they can look at me, let out a sigh and say, “me too.”

I have dozens of examples of doing this on a daily basis. Just ten minutes ago, I had an opportunity to train my vulnerability muscles.

“I love your tattoo,” she said.

“Thanks, I like it too. I used to not though. I got it during a break-up when I was in Thailand. It was almost like an act of defiance, saying, “You don’t own me, I can do what I want!” It was an immature, egotistic motive to feel like I was reclaiming my life. At the same time, it happened during a transformational time in my life that did lead to a lot of personal growth. I was reminded of pain for a while when I looked at it, but now I see growth and love. I like it now.”

She looked at me, nodded her head and said, “I’ve done that too…” gliding into her own story.

Not every conversation needs to be a heart-opening story time, but when you feel like the energy is there, and there’s potential for something good to come out of it, I say do it.

It’s this kind of thinking that led me to share the time I went to jail with my thousands of listeners.

It’s this kind of living that helped me to cry openly on Snapchat when I re-homed my first dog.

It’s this kind of dating that’s helped me to decipher which relationship is going to go somewhere, and which one will not.

There are five specific ways I’ve realized you can promote vulnerability in a partnership. Incorporate these points into all your relationships, and you’ll experience more authenticity in your conversations, growth and self-awareness.

1. CREATE THE SPACE (even if you have to go first)

“I have a deep-seated desire to be special, known, or maybe even famous. This is no good because it taints my message and work. I’d rather my work be purely motivated by serving others, but sometimes my desire to be unique and “different” can take over. It’s something I have to keep an eye-out for. I also know that this is an innate desire of all people, so I don’t judge myself for it. I just keep a look out for it. What’s something you’re working on?”

It’s not always easy to go first because you have no idea how the person is going to respond, but who cares? I would hate to live my entire life with people who have no depth because I was afraid to create depth out of fear they wouldn’t like it.

There are some people I know don’t want to open up to me and that’s fine, but those people are not my closest friends or romantic partners. If they do not share first, you go on ahead and create that space.

Personally, I have a lot of masculine energy and it’s something I’m actively trying to balance out (hellooo, more vulnerability for you) so I am highly attracted to men who take the initiative to start this conversation first, so I can follow suit. With that said, I’m more self-aware than the average joe so I don’t mind creating the space first. Either way, you can’t be vulnerable if you don’t get vulnerable. Start somewhere.


Do you really want to know your partner’s insecurities? Or do you ask “What about you?” only so that you can hurry up and talk about your own problems again when he’s done.

Slow down, listen and ask your partner questions. Ask him what he’s going through. Probe. Create more and more space.

“Why do you think you feel that way, honey?”

“Where do you believe this all began?”

“And what are you currently doing to become more aware of this?”

Don’t let your mind wander off to how you’re going to contribute to the conversation immediately when he finishes talking, but actively listen to what he/she is sharing and get as curious as you can so that you know how you can help him along in this journey.


What is it that you both want to get out of the conversation?

Say you’re coming home from work and you had an especially rough day. Your boss got onto you for an assignment that came out “completely wrong.” Your deepest insecurity at the moment is that you’re not pleasing your boss and you’re going to be fired at any moment. This comment hit you way harder than your boss probably knows because of the fact that he hit such a sensitive spot in your heart.

When you come home to your boo, don’t just start laying it all out there. Set up the conversation so that you get what you need out of it and there’s no room for miscommunication.

Let your babe know you just need to be heard. You don’t want advice, commentary or to have the problem “fixed.” You just need fifteen minutes to share and release the shame.

Or maybe you do want their insight. Let them know that too. Either way, preface the conversation so your partner knows what you need to get out of that time.


Sharing time is great, don’t get me wrong, but there’s something really sexy about being called out on your own bullshit in a loving way. If you have an insecurity that needs some work, having a partner help you along can be a great way to get “free” coaching. If you want to work on your insecurity, allow him or her to open up a conversation around it whenever it comes up.

“Ugh I really wish that NBC News would pick up on my story,” I said.

“Is that because you want the exposure, or you think it would help others?” he asked.

“Hmm….that’s a good question. I think it would definitely help my message get out more…but I think the desire to be on global news is for myself. To say I “made it”…” I said back.

“How can you authentically serve more people now without it being about you?” he asked in return.

Truth be told, the desire to be on the news is an ego-stroker. Sure, it would help my message but deep down in my heart I knew that the desire came from an egotistical place. And I think it’s pretty dang sexy that someone would bravely call me out on it.

This same process can be applied to pretty much all insecurities. Maybe you are afraid that people are judging you all the time. Your boo can help push you to do things you wouldn’t normally do, wear things you wouldn’t normally wear, or act a way you wouldn’t normally act, so that you can get closer and closer to the most authentic version of you. Tell him or her to help you stop caring so much about what other people think, and call you out (privately) whenever you’re people pleasing.


Insecurities pop up all the time. There are fresh, new wounds that need mending on a regular basis and it’s all too easy to keep them bottled up. Check-in with each other often about what you’re going through and what new areas you feel the most vulnerable about in your life.

I have a “Self-Improvement” folder in my Evernote where I keep various notes, such as quotes I love and people I admire, but one of the recent documents I’ve created is a “Things I Need to Work On” page. This is a document where I call myself out on things that I realize I want to change or strengthen. These things also happen to be the things I don’t want people to know about (aka shame) and exactly what I should be sharing (being vulnerable). My partner would be the first person to know about the things that make it to this list, and I suggest the both of you do the same.

What if you’re not in a relationship? If you’re dating, the same applies. It might not be possible to call each other out (it takes awhile to get there) but you can easily open up a conversation around vulnerabilities at the beginning phases of a relationship. You can ask over coffee, or even over text. This will quickly take your relationship from surface level to deep diving.

If you’re like “WTF MADDY. I can’t do that! That’s so awkward!” then obviously you’re the best candidate for it. Start opening up this conversation on all your dates and see what happens. I promise, you’ll find yourself creating more authentic conversations and never will it be a wasted moment. Even if you don’t receive the same insightful honesty from the person you’re with, you’ll be healing your own heart simply by sharing.

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