100 Intimate Moments

Get Naked! Gain Confidence!

“The verb ‘intimate’ means to make known or to reveal. Genuine intimacy in human relationships requires dialogue, transparency, vulnerability and reciprocity.” But where do we begin?

In an effort to increase intimacy in the relationships in my own life, I have spearheaded one of the most terrifying but transformative projects I have ever been associated with.

I realized with dismay that somewhere along the path of ‘growing up’ I had lost the ability to reveal myself, make myself vulnerable. I want to be playful, courageous and connected in my life, but it is difficult when wearing a rigid shell of self-protection.

In a courageous attempt to challenge myself to leave this mask-wearing-comfort zone, I have pledged to have 100 Intimate Moments to add more emotional depth and connection to conversations. Here are the ground rules:

1. Confidentiality.

2. 60 minutes together in an undisturbed place (can be video conference).

3. We are sober, present and willing to get uncomfortable.

4. I go first.

I am a third of the way through the challenge, with 30 conversations below my belt, and I cannot say, the conversations get any easier. Every single one has me terrified beforehand. Sometimes I am so afraid, I feel physically ill. But my desire for more spontaneity and increased connection in my life makes me take the plunge into the pool of suspense over and over again.

It is one thing to coach people, where my focus lies 100% on the client and their vulnerabilities, blockages and dreams; it is another thing entirely to open myself up. In these Intimate Moments, I share parts of myself that I’d rather hide, parts for which I might get judged, misunderstood or rejected. This has been my single biggest fear throughout the process: “What if the relationship ends over this?” “Good riddance!” you might think, but the danger feels real. Fear has a way of feeling disproportionally more substantial than the threat that triggered it in the first place.

Last week I had an Intimate Moment with a person whom I have known and loved for a long time. Yet there is something I had never shared with her, a fear of mine I have never expressed. Ahead of our conversation, I feel anxious. There seems to be a lot at stake with this person. What if this is a part of me that is unacceptable to her? I’m having palpitations, battling until the last moment whether to really bring this up or come up with a less intense, less vulnerable version for this conversation. I tell her, quickly, before I change my mind:

“I love you. I’m afraid I will lose you to your new husband.” As I say it a part of me silently comments: “You sound so needy, now you will lose her, you should play it cool. You are being selfish.”

Her reply is prompt: “I’m so glad you are telling me. I had the same thoughts about us. I’m afraid our relationship will change and that I will lose you as a friend.”

The space between us transforms instantly. It feels healing. There is an incredibly strong sense of connection. There is even more love and less doubt between us. I feel closer to her than ever — even though I did not think that was possible.

Whilst I felt there was a lot at stake with my friend, Intimate Moments with random people are just as petrifying. Take this very successful tech entrepreneur I met at a sporting event. I told him about the project and he said “I’m in.” When I tried to go a little beyond the surface at the sports event, he immediately went back into his safe zone. He became extremely intellectual, tried to impress me with random facts, a common defence mechanism I see both in clients and myself when conversations become uncomfortable. (There are plenty of others, including changing the topic, cracking a joke, feeling tired, mentioning sudden physical pain or physically leaving the situation altogether.)

This person clearly is very intelligent, experienced, educated and successful. How do I initiate an Intimate Moment with HIM, when even the prospect of a little more depth triggers such a strong defence? When the time approaches, again, dread…to the point of actually wanting to cancel the call. How am I going to be able to go deep with a perfect stranger? Why make myself vulnerable in this situation? What if he says something that completely catches me off guard and I won’t know how to respond? (Something that happens often) What if we go into awkward silences for really long periods of time? (This too, is a regular occurrence.) I vow not to bridge silence with superficial chit-chat or any other form of diversion to distract from uncomfortable moments.

Upon entering the conversation with him, the option of playing it safe arises again, but after sharing the initial ground rules, I tell him: “I’m surprised you are up for the challenge! Why do you want to do this?”

He responds: “Because your project sounds interesting and I’d like to support you with it.”

Pause… nothing else… nowhere to go.

I come up with a different question. I do not ask questions in every Intimate Moment. Sometimes people already know what they want to talk about.

“What I usually hide from people is….”

To my surprise, he goes first. In an impressive and very touching manner he starts to share something he has never shared with anyone: “I feel very insecure about my background. I feel out of place, as if I don’t belong. I wish I had gone to one of the Ivy League universities.”

I sense that admitting this does not come easy to him. I feel relief, tremendous relief because I can relate to what he is sharing. I have had moments of insecurity about my background, insecurity of having grown up in an all-white environment as a mixed-race child. I have also carried the insecurity about not having gone to an Ivy League university. I share all of this with him and…the fact that I have met plenty of Ivy League graduates who, despite having been top of their class, still carry a deep-seated insecurity about their background. Some feel like they’re hiding behind a label, regret not having had the courage to go after what really matters to them, and, deep down, still question who they really are. “When I touch on anything I truly love in life, I feel safe.”, I add.

I remember the man at the sporting event, wearing his grown-up mask. That person felt intimidating and miles away. The person I see now, the person who talked about his insecurity, feels close. The space between us has shifted. It feels warmer, gentler, tender and soft. I see a beauty in the person before me that I couldn’t make out before. I feel a connection. I am willing to be more of myself with him. I am impressed with this man’s courage. He owes me nothing, he agreed to participate on a whim and he showed up more powerfully than I would have ever imagined.

Intimate Moments started as a challenge to myself, but very quickly, I experienced that there is much more to the project. It has the power to transform the space between us, to facilitate a deeper sense of connection. It gives us confidence. Core-confidence, not the superficial and conditional kind that is based on achievements.

So I added another rule:

5. Pay it forward.

Make yourself a little more vulnerable with another person in your surroundings and watch what happens. I have received astounding feedback of people who did pay their Intimate Moment forward and saw a transformation in their relationships with others.

Every time ahead of an Intimate Moment conversation I feel like I am about to take a plunge into the ocean on a moonless night. I cannot see below the surface. I don’t know who or what else will be in there with me and I have no clue what the water will feel like.

The only way to find out is to jump.

It is terrifying, but coming out the other end always feels worth it a million times over.

I am very grateful to all the courageous individuals who have and currently are participating in 100 Intimate Moments. If an Intimate Moment conversation is something you would like to experience, or you would like more information please reach out. We can take a first step together from there.

This article appeared originally on Medium.