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Unhinged, A Dating Series: A Lesson in Ego

Editor Nicolle Monico heads to a singles event with matchmaker Sophy Love and learns that a little discomfort makes for the best conversations
Unhinged, a dating series: Nicolle Monico

In Unhinged, San Diego local and SDM editor Nicolle Monico shares her experiences dating in the city while hopefully finding love in the process

“What I’m hearing is that you don’t like to be the one answering questions because you don’t feel like you have much to offer,” says a stranger sitting in front of me, five minutes after I meet him.

I start to sweat. This happens a lot when I get nervous, and not in a charming way. It’s the kind that lingers on your upper lip as you talk so you’re continually wiping your face. 

With no plans for Valentine’s Day, I’d decided to take part in a Feb. 14 singles event hosted by matchmaker Sophy Singer of Sophy Love. As a group, we’ve just finished an hour-long workout, but this is the first moment where my sweat feels embarrassing. 

I’m sitting in a large circle. It feels as though neon signs blink overhead, calling out my insecurities, as I scan the room of 25 other singles. We begin the second half of the mixer, starting with a meditation before discussing “authentic relating,” a concept that author Ryel Kestano laid out in his book Authentic Relating: A Guide to Rich, Meaningful, Nourishing Relationships

As we meditate, I question why I’m here, who I could ever meet in this environment. Is finding a partner just not for me? Is everyone else as uncomfortable as I am?

Being a little uncomfortable is kind of the point, though. Authentic relating is designed to slice through the shallow pleasantries of the typical first date. “When you practice authentic relating, you are bringing your whole self into the relationship,” Singer says. “You’re not strategizing; you’re not playing games; you’re not changing yourself to be some version that you think the other person is going to like better than the real. And being seen and heard is healing.”

Kestano defines three levels of conversation: informational (pure facts), personal (feelings about facts), and relational. 

“[The relational level] is a conversation where you are revealing your experience and what it feels like to be in this moment with the other person. It is always new,” Singer explains. “It is unscripted. This moment that we are having here has literally never happened before.”

According to Singer, level three is the game-changing key to connecting authentically with others. She asks us to share with each other what is “alive” for us in this moment. In less woo-woo terms: How are you actually feeling as you’re being asked to get to know this person?

As we follow Singer’s prompts, my conversation partner zeroes in on the fact that I tend to push attention off of myself because I don’t enjoy feeling vulnerable with strangers. (Truthfully, this column is not easy to write, at all.)

It’s a far cry from the “What do you do?” convos I usually have with acquaintances. In this setting, I couldn’t feign perfection and hide the parts of me that feel complicated or weak. But neither could he.

As we spoke, I learned that he had never participated in any type of dating meet-up or event like this and that it was overwhelming for him—so much so that during a mid-session break, he quietly slipped out and went home. Nevertheless, our mutual willingness to analyze our reactions and interactions humanized him. I found myself caring about him more than I would have had we just prattled about our favorite hobbies. 

This is what seems to be missing in dating right now. Frustrated and fed up by endless failed dates and used to the split-second decision-making of swiping on apps, we might find it difficult to muster the energy to really connect with someone new, at least until we’ve assessed whether they’re worth the effort. 

But maybe that’s the problem. What if we approached every date as a chance to engage with an interesting new person, whether or not it leads to a relationship? Every stranger has a story to tell. “We think that people connect to the glossy version of ourselves,” Singer says. “ But actually, where most connection takes place is with the messiest parts of our human experience.” 

And, if we buy into Kestano’s words, being willing to get deep right away can help foster relationships built on honesty, integrity, trust, and wholeness.

The singles event wasn’t what I had expected, and it wasn’t always easy to release my ego and follow Singer’s suggestions. But I’m glad I went. The thing is, though, I’m nervous to share this post this week, because it all feels so obvious. 

Yet, from what I’ve seen—and read in the flood of DMs I’ve received since starting this series—we’re not actually putting these ideas into practice. Could our perspective on dating change if we started seeing one-off dates as a good thing—an opportunity to learn something new about others and ourselves?

After all, I didn’t meet anyone that night, but I did use some of these methods on my first date with Connor (not his real name) this past Monday. He asked me out again (more on this later). Maybe he was attracted to my mess.

As always, thanks for following along. See you next Friday!

Follow along for all the fun and updates at @monicles and @sandiegomag.

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By Nicolle Monico

Nicolle Monico is an award-winning writer and the managing digital editor for San Diego Magazine with more than 15 years of experience in media including Outside Run, JustLuxe and The San Francisco Chronicle.

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