“If I were you, I would move this here,” he said, gently gripping the bright pink tube of Baby Lips in a gray hooded sweatshirt as he looked intently at Cartel Coffee’s portable chess board.

“Mmm hmm,” I murmured back, pretending to absorb the information. An attempt to learn chess was hijacked by the cute way he sincerely stared at my various lipglosses who acted as substitutes for missing chess pieces.


On our first dinner date, only a couple weeks before, I hoped he didn’t notice as I quickly snuck from the seat across the table to the one adjacent to him. I just wanted to be closer. Similarly, when he looked up from the chess board with a smile, I held myself back from audibly admitting what I was oddly thinking: “I want to squeeze you.”

Later that day I returned home and unpacked groceries while dancing towards the refrigerator, far too excited to stock its shelves. Just then a text was received, and I ran across the kitchen to check. It was from him: “I want to squeeze you.”


3 Years Later

The CVS bathroom on Goldwater Avenue was surprisingly roomy which semi-eased my anxiety as I ripped open packages of mascara, travel-sized toothpaste and a toothbrush. My face was makeup-less from a quick morning shower and major brain fart.

In a rushed attempt to make it to the coffee shop by 7:30 a.m. I left my travel cosmetic bag sitting on the coffee table of my friend’s condo where I stayed the night. After quickly brushing my teeth and bringing life to my lashes under the fluorescent lights, I dumped the evidence in the rental car, applied some deodorant and ran across the street to Sip Coffee.


I swung the door open like a hot mess and found him sitting in an antique padded chair waiting with a coffee. It was the first time seeing him since coffee shop chess three years before.

The True Hard Work of Love and Relationships

“We’re still at the very beginning of understanding ourselves as human emotional creatures. We’re still taking our first baby steps in the understanding of love, and we need a lot of compassion for ourselves. And no wonder we make horrific mistakes pretty much all the time.”

Alain de Botton wrote The New York Times most-read article of 2016, “Why You Will Marry the Wrong Person” and in his latest interview with Krista Tippett on OnBeing, his wisdom hit home. Consequently I’ve listened to the podcast on repeat which led me to recall one of my many mistakes that occurred in that kitchen 3 years before.


“I want to squeeze you.” The joy of mutual feelings mixed with the shock that there might be someone else as weird as me caused my cheeks to hurt from beaming so big as I looked down at the text. However, at the same moment, my mind subconsciously slipped into self-sabotage and fear took hold. Within 48 hours I imagined enough reasons that it wouldn’t work to send the “just friends” text, and that was the end of joint Shark Tank watching, healthy habit tracking and chess lessons. I didn’t see him again.

Until sitting across from him at Sip Coffee in workout clothes and CVS mascara, drinking an early morning mimosa to calm my nerves and rambling about what I had learned about life in the past 3 years. It was Annie-uncensored, and somehow he was still unfazed.

As we hugged goodbye it was hard to recall why I abruptly ended things and allowed time to lapse.


Why Did the “Just Friends” Talk Happen?

“The darker side of online dating is that it encourages the idea that a good relationship must mean a conflict-free relationship, and therefore, any relationship which has conflict in it, which has unhappiness and areas of tension in it, is wrong and can be terminated because we have this wonderful backup, which is alternatives,” Alain de Botton explained to Krista Tippett.

It wasn’t that I wanted alternatives, and it certainly wasn’t that we experienced any conflict within the few weeks of knowing each other. However, as a born-again virgin to relationships, I anticipated potential conflict like a chess master would predict the direction of his opponent’s pieces.

While I don’t recall the minute chess rules he tried teaching me via Baby Lips, I do remember the general guidance that was given regarding the game: You must be strategic and think two – maybe three or four – steps ahead, anticipating the other’s next move.


Without realizing it, I’ve been applying the rules of chess to dating, including him. From a simple, sweet text my mind jumps to commitment. From there my brain begins searching for potential flaws that would disrupt it. I mean, why didn’t he take my advice on the name of his startup? And how could I date someone who lived Downtown?

Flawed Participants

“And we feel in a way that we know them already, and we impose on them an idea…” Alain de Botton said in regard to the preconceived notions we hold about people, whether we just met them or have known them for years.

I thought that I knew him. I thought that I knew exactly what I wanted. And I thought I knew the next move. Which is something that I now realize I’ve done for years – both before and after the chess game – and that I still do with great guys today.


Since meeting at the coffee shop in late October, we’ve become actual friends. We texted over the holidays when both our families drank too much egg nog for their own good, in which I finally confessed the reason for an abrupt goodbye.

“You gotta chill I think. I don’t know you all that well, but I think you might be putting relationships on a pedestal,” he said in response to my long explanation on why I prefer friendships to the riskiness of relationships.

A Flawed Game

“And sometimes, we bring to adult relationships some of the same hope that a young child might have had of their parent.. And, of course, an adult relationship can’t be like that. It’s got to accept the person across the table or on the other side of the bed is just human, which means full of flaws, fears, etc., and not some sort of superhuman,” said Alain de Botton.

Flawed participants inevitably lead to a flawed game. But perhaps it’s more about how the game is played.


When it comes people, I’ve realized that flaws are in our favor. In the same way that he texted me, “You’re awesome” after witnessing the disheveled 7:30 a.m. mimosa mess. And when it comes to the game of dating, I’ve realized it’s not like chess. You don’t want to think two steps ahead. It’s not in your favor to be strategic. And the next move doesn’t matter. You must enjoy the simple Friday movie night-in, the nervous first kiss on the beach or a friendly chess lesson.

Because maybe the thing we should be concerned with are the pink tubes of lipgloss that we’re holding. While the pieces aren’t perfect, perhaps it’s the unknown, the excitement and the potential of a checkmate that make it worth the while.